20 Fun Facts About Ocean’s Eleven

By jon o'brien | dec 7, 2021.

George Clooney and Brad Pitt star in Steven Soderbergh's Ocean's Eleven (2001).

Has any other popcorn flick boasted a more impressive star-studded cast than Ocean’s Eleven ? Well, apart from Ocean’s Twelve , Ocean’s Thirteen , and the female-fronted reboot Ocean’s 8 , obviously. There was George Clooney , Brad Pitt, Matt Damon, and Julia Roberts all at the peak of their powers; past and future Oscar favorites Andy Garcia, Don Cheadle, and Casey Affleck; and Hollywood royalty Carl Reiner and Elliott Gould—not to mention a cameo from everyone’s favorite German-American lion tamers Siegfried and Roy. Even better, the remake of the 1960 classic was actually good! Here are 20 little-known facts about the caper that even-out cooled the Rat Pack .

1. Ocean’s Eleven nearly starred the Wilson brothers.

Scott Caan and Casey Affleck in Ocean's Eleven (2001).

A then-relatively unknown Casey Affleck and Scott Caan more than held their own against their A-list co-stars as siblings Virgil and Turk Malloy. But a real-life pair of brothers were initially tapped to play the crafty mechanics. Yes, director Steven Soderbergh’s first choices for those roles were Luke and Owen Wilson , but the pair had to pass due to their commitments on The Royal Tenenbaums . Owen, in particular, is unlikely to have regretted the decision: Alongside regular collaborator Wes Anderson , he picked up an Oscar nomination for Best Original Screenplay for the dysfunctional family dramedy.

2. Mark Wahlberg turned down a role in the movie.

Mark Wahlberg’s loss turned out to be Matt Damon’s gain as the one-time Calvin Klein model was the first actor to be offered the part of pickpocket Linus Caldwell. However, another remake of a ‘60s classic, Planet of the Apes , proved to be more tempting. Despite the latter’s critical mauling, Wahlberg doesn’t appear to believe he missed out. In fact, he later told Today , “People tell George Clooney it's great, but we all know it sucked ... I made two bad movies instead— Planet of the Apes and The Truth About Charlie —but doing that was better than sitting with Brad and George, telling the press how great everybody is!”

3. Bruce Willis also passed.

Bruce Willis might now be stuck in VOD action movie purgatory. But in 2000, he was still one of Hollywood’s most bankable names. Little wonder, then, that Ocean’s Eleven producers approached him to appear in their star-studded ensemble. Unfortunately for both parties, this approach came just a little too late. Indeed, Willis told WENN , “By the time I got to it, all the good stuff was done and I wanted to play one of the gang.” The tough guy must have gotten a case of FOMO, though, as he did sign up for Ocean’s Twelve , despite the fact the role was a minor one playing himself.

4. George Clooney is not a fan of the original 1960 movie.

George Clooney starred in all three installments of the Ocean’s trilogy and served as executive producer on Ocean's 8 . But his commitment to the franchise certainly doesn’t stem from a love of the original movie. In the production notes for Ocean’s Eleven in 2001, Clooney claimed that the 1960 version’s "classic" reputation is only built on its star power: “Everybody will say, you know, ‘Oh, that’s one of my favorite films,’ and I’ll always say, ‘Have you ever seen it?’ The truth is, most people never saw the original Ocean's 11 .”

5. Julia Roberts was wooed with a $20 bill.

Back at the turn of the century, when she’d just been awarded the Best Actress Oscar for Erin Brockovich , Julia Roberts was the highest-paid actress in Hollywood. But the fact that she reportedly commanded a $20 million fee didn’t deter Clooney from courting her for the role of Danny Ocean’s ex-girlfriend Tess. In fact, he played upon her costly status by sending her a screenplay attached with a $20 bill alongside the note, “I hear you get $20 a picture now.” Roberts obviously appreciated the cheeky gesture as she signed up for the part and reprised it in the sequel, too.

6. Every actor took a significant pay cut to appear in the movie.

Roberts might not have come on board for just $20. But like her Ocean’s Eleven castmates, her paycheck wasn’t quite as hefty as she was accustomed to. Clooney led by example by offering to cut his salary to get the movie made. "We said, if we all get paid, we can’t make the movie, so why don’t we all just take a big chunk of the back end, work cheap, and see if there’s any money at the end," Clooney explained to WENN . The gamble paid off: The movie grossed $450 million worldwide—five times its budget and over three times the Ocean’s gang’s haul.

7. Don Cheadle apologized for his accent.

Keanu Reeves in Bram Stoker’s Dracula . Josh Hartnett in Blow Dry . Dick Van Dyke in Mary Poppins . Don Cheadle unwittingly joined the exclusive club of all-time worst English accents ever to grace the big screen thanks to his Ocean’s Eleven performance as Cockney explosives expert Basher Tarr. “His utter dismantling of the British accent is not just bad, it's disastrous,” TIME magazine said in one of the more favorable reviews. Even worse, it was apparently the Oscar nominee’s idea to give the character a London twang. While accepting the 2007 Spirit of Independence Award at the Los Angeles Film Festival, Cheadle apologized for his cinematic crime: "Forgive me! I won’t do it again!"

8. Rusty’s snacking habit was Brad Pitt’s idea.

While Cheadle made things more difficult for himself by giving his character a Cockney accent, Brad Pitt did the same by suggesting that career criminal Robert "Rusty" Ryan should always be snacking. The actor believed that with all the planning that goes into a multi-million dollar casino heist, square meals wouldn’t be an option. Essentially getting paid to eat may sound like the dream, but the scene where Rusty is waiting for Roberts’s Tess had to be re-shot so many times that Pitt ended up consuming a sickly 40 shrimp.

9. There are cameos from two of the original movie’s cast members.

Sadly, the majority of the original film's main cast members, including the legendary Frank Sinatra , Dean Martin , and Sammy Davis Jr. , had passed away by the time that Clooney and co. stepped into their shoes in 2001. But eagle-eyed viewers may well have spotted two of its surviving stars in brief cameos. Henry Silva and Angie Dickinson, who played gang member Roger Corneal and Danny’s wife Beatrice Ocean in the Rat Pack version, briefly appear during the boxing scenes filmed at the MGM Grand. It was Silva’s final big screen appearance and Dickinson’s penultimate.

10. Lennox Lewis’s Ocean's Eleven cameo harmed his boxing career.

Lennox Lewis can briefly be seen sparring against Russian giant Wladimir Klitschko in the boxing ring in Ocean’s Eleven . But the two days he spent filming the scene in Las Vegas ended up costing him three world titles and a bumper pay deal worth $75 million—according to his one-time promoter, anyway. Panos Eliades told The Guardian that his former client’s Hollywood detour gave next opponent Hasim Rahman an advantage in the training stakes and ultimately allowed the American to pull off a shock victory. Eliades called Lewis’s timing crazy, adding, “And does he think that Julia Roberts will want to know him now that he's an ex-champion?”

11. Don Cheadle asked not to be credited.

Scan the credits of Ocean’s Eleven and you’ll notice one major name missing. Indeed, Cheadle asked for his performance as Basher Tarr to go uncredited—and not because he was embarrassed about the mess he made of the character’s accent. The actor later explained to Black Star News , “With Ocean’s , there was some stuff that happened behind the scenes that I didn’t like how it went down, so I just said, ‘Take my name off it.’” While what exactly went down has never been confirmed, the rumor mill version is that Cheadle wanted top billing right alongside Clooney, Pitt, and Damon; when he was told no, he allegedly asked that his name be removed completely.

12. Shaobo Qin had never acted before.

Shaobo Qin almost stole the show from under all the A-listers’ noses with his acrobatic performance as The Amazing Yen. Who can forget that gravity-defying backflip in the vault, for example? Remarkably, the China native had never acted before landing his role in Ocean’s Eleven —producers spotted his talents during a rehearsal with the Peking Acrobats in Las Vegas. Qin is one of only two names to appear in all four of the 21st century Ocean’s movies, with Elliott Gould as one-time casino owner Reuben Tishkoff the other (Damon’s cameo in Ocean’s 8 was cut from the final edit).

13. A scene had to be re-shot post-9/11.

The hotel that Tess and Terry see being demolished by explosives is an entirely fictional one named The Xanadu. But when the scene was filmed, the two characters were meant to be witnessing the demise of the New York-New York Hotel and Casino. After the tragic events of 9/11, producers worried that audiences would be reminded of the World Trade Center and so set their CGI team to work to create an alternative just in time for the film’s December release. The original version, however, can still be seen in the DVD special features.

14. The film took over the Bellagio Hotel & Casino.

Las Vegas’s hotels will typically restrict any disruption from film and TV production to the twilight hours. But thanks to producer Jerry Weintraub’s friendship with Bellagio owner Steve Wynn, the Ocean’s Eleven crew were pretty much given free rein. Approximately 30 percent of the hotel’s casino floor would be taken up by the movie shoot at any given time, while its famous fountains, valet parking, and botanical gardens were regularly shut down, too. But director Soderbergh recognized that the Bellagio was handsomely rewarded for being so accommodating, remarking in the production notes , “The movie is like a two-hour commercial for Las Vegas and the hotel.”

15. Steven Soderbergh wasn't sure he was the right director for the movie.

It’s hard to imagine Soderbergh, a pioneering name in independent American cinema—who’d just picked up a Best Director Oscar for Traffic —having job insecurities. But while promoting Ocean’s Eleven , the filmmaker admitted to the BBC that he had doubts about his suitability for the heist caper. “To my mind there is a certain technical standard involved in making a film like this, and I was concerned that I wouldn't measure up, so I made sure that I did a lot of homework,” he said. The movie’s success must have reassured Soderbergh as he also took the reins for 2004’s Ocean’s Twelve and 2007’s Ocean’s Thirteen .

16. The cast was forced to hang out together.

The natural camaraderie between all the heist crew is one of the main reasons Ocean’s Eleven works. And it was built up thanks to the producers’ insistence that all main cast members needed to be as sociable off-camera, too. In the film’s production notes , Weintraub remarked, “It wasn't hard to do because they all liked each other and as soon as they started spending time together away from the set, real friendships developed.” Indeed, Pitt and Clooney, in particular, have become renowned for their long-lasting bromance, also appearing together in 2008’s Burn After Reading .

17. A friend tried to steal Bernie Mac’s role.

With friends like Steve Harvey, who needs enemies? In 2003, Bernie Mac revealed to Ebony magazine that the Family Feud host, whom he’d toured alongside for the hit documentary The Original Kings of Comedy , had tried to steal his part in Ocean’s Eleven . Apparently a Harvey representative contacted producers to inform them that their client would be far more suitable for the role of blackjack-dealing conman Frank Catton. "The Hollywood game that we are in, it's a cold game," Mac said. "And the sad thing about it is all of us are doing well, so I don’t really see the problem."

18. It shared a prop with Austin Powers.

Ocean’s Eleven is surely the only example of Pitt having something in common with buck-toothed horndog Austin Powers . The unflattering wig that Rusty sports in a bid to pass as a doctor is the very same one that Mike Myers wore during rehearsals for his comic creation’s first big-screen outing, International Man of Mystery . Pitt reportedly compared the hairpiece, which he complements with a pair of spectacles that also wouldn’t look out of place on the groovy secret agent, to a beaver when first presented with it by the make-up team.

19. The pinch is real.

In one of the film’s most pivotal scenes, Cheadle’s Basher Tarr manages to knock the casino’s entire power source out for several seconds with a device dubbed "a pinch." It may look like the work of fiction, but in fact, production designer Phil Messina got the idea from real-life scientists. He explained in the production notes , “We did a lot of research early on because we wanted to at least have it be based on reality ... We went into chat rooms and basically posed design questions. Then our property master visited a lab in Northern California that had a pinch and he brought back photographs and diagrams.”

20. Ocean's Eleven proved George Clooney was a terrible gambler.

George Clooney, Brad Pitt, Matt Damon, Elliott Gould, and Don Cheadle in Ocean's Eleven (2001).

While Damon had competed at the World Series of Poker and appeared in the high-stakes drama Rounders before signing up to Ocean’s Eleven , Clooney was a complete gambling novice. The Good Will Hunting star told the BBC that the film’s leading man was reluctant to take a chair at the casino they frequented during filming, and it turns out with good reason. He subsequently lost at blackjack an incredible 25 times in a row. "I was sitting there thinking the mathematical probability of this is mind-boggling, I can’t believe you haven't won yet," Damon said.

Brad Pitt Admits To Shamelessly Stealing Matt Damon’s Identity

"They'll figure it out later."

Brad Pitt Admits To Shamelessly Stealing Matt Damon’s Identity

As it turns out Brad Pitt is regularly mistaken for fellow actor Matt Damon. So, Pitt just fakes Damon’s signature.

You’d think everyone would be able to recognise Brad Pitt; the dude is one of the most famous actors on the planet. He’s starred in some truly iconic films – like Seven , Ocean’s Eleven and Fight Club – and has won multiple awards, including two Oscars.

And yet, apparently, some people regularly bump into Pitt and mistake him for Matt Damon. An old clip of Pitt has resurfaced online and the actor – who’s won People ’s Sexiest Man Alive award twice – says people confuse him for Damon all the time.

Pitt also admitted that he doesn’t correct these fans and instead just signs autographs as Damon.

“I’ve actually signed autographs as Matt… They’ll figure it out later.” Brad Pitt

The short clip has obviously been taken from an interview where Pitt along with Leonardo DiCaprio and Margot Robbie were promoting the 2019 film, Once Upon a Time in Hollywood . And in the same clip, DiCaprio says he also gets mistaken for Damon.

“I get Matt Damon.” Leonardo DiCaprio

DiCaprio obviously corrects people when they confuse him for Damon though, as he looked shocked (but also amused) when Pitt admitted to faking Damon’s signature; Robbie exclaimed “Really?!”

Just when you think Pitt couldn’t get any cooler, he admits to doing something as hilarious as this… And for those of you who have met Matt Damon and got his signature, maybe double-check that it wasn’t Pitt.

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Ocean's Thirteen

Brad Pitt, George Clooney, Don Cheadle, Matt Damon, Andy Garcia, Casey Affleck, Elliott Gould, Scott Caan, Bernie Mac, Carl Reiner, Eddie Jemison, and Shaobo Qin in Ocean's Thirteen (2007)

Danny Ocean rounds up the boys for a third heist after casino owner Willy Bank double-crosses one of the original eleven, Reuben Tishkoff. Danny Ocean rounds up the boys for a third heist after casino owner Willy Bank double-crosses one of the original eleven, Reuben Tishkoff. Danny Ocean rounds up the boys for a third heist after casino owner Willy Bank double-crosses one of the original eleven, Reuben Tishkoff.

  • Steven Soderbergh
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  • 1 win & 5 nominations

Ocean's Thirteen

  • Danny Ocean

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  • Linus Caldwell …

Michael Mantell

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Al Pacino

  • Bank's Junior Executive

Eddie Jemison

  • Livingston Dell

Don Cheadle

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Shaobo Qin

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Scott Caan

  • Turk Malloy

Bernie Mac

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Carl Reiner

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  • Trivia Matt Damon's London street scene--showing Linus walking through London speaking on the phone--was shot while Matt Damon was in London filming "The Bourne Ultimatum". The Ocean's Thirteen production took advantage of this happy coincidence as they wanted the character Greco to be a British classmate of Roman Nagel. Thus Linus's being in London played well to the story.
  • Goofs When Yen places a bet on the roulette wheel, he covers numbers 11,12 and 13, to fit in with the previous statement that the 'fixed' ball could be assumed to land on one of three numbers. 11,12 and 13 do not appear consecutively on a roulette wheel. If you wanted to cover a bet on '12', for example, you'd need to place chips on 12, 8 and 29 on an American table.

Terry Benedict : [referring to Danny donating Terry's share of the money to charity] You think this is funny?

Danny Ocean : Well, Terry, it sure as shit ain't sad.

  • Crazy credits Each of the logos from the studios involved in the opening sequence is colored a dull blue color, a throwback to the original studio cards from "Ocean's 11"
  • Alternate versions Two versions are available, depending on your location, the original theatrical release and an edited cut in Croata. Runtimes are "2h 2m (122 min)" and "1h 54m (114 min) (Croatia)", respectively.
  • Connections Featured in Siskel & Ebert: Pirates of the Caribbean: At World's End/Bug/Knocked Up/L'iceberg/Severance (2007)
  • Soundtracks Don't You Want Me (1981) Written by Jo Callis (as John Callis), Phil Oakey (as Philip Oakey), and Philip Adrian Wright (as Adrian Wright) Performed by Martin Blasick

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  • June 8, 2007 (United States)
  • United States
  • Warner Bros (France)
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  • Bellagio Casino & Hotel - 3600 Las Vegas Boulevard South, Las Vegas, Nevada, USA
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  • $85,000,000 (estimated)
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  • Jun 10, 2007
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  • Runtime 2 hours 2 minutes
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Brad Pitt, George Clooney, Don Cheadle, Matt Damon, Andy Garcia, Casey Affleck, Elliott Gould, Scott Caan, Bernie Mac, Carl Reiner, Eddie Jemison, and Shaobo Qin in Ocean's Thirteen (2007)

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Matt Damon Was the Third Choice for His ‘Ocean’s Eleven’ Role

  • A-list actors like Mark Wahlberg and Johnny Depp turned down roles in Ocean's Eleven , but now regret their decision due to the franchise's continuing popularity.
  • George Clooney used his wit to convince Julia Roberts to join the cast, attaching a $20 bill to the script to reference her high paycheck.
  • Other actors considered for roles in the film included Owen Wilson, Ewan McGregor, the Coen Brothers, Ralph Fiennes, Mike Myers, and Alan Arkin, showcasing the high demand and competition for the star-studded cast.

In 2001, Steven Soderbergh assembled a team of Hollywood's finest movie stars to star in his remake of Ocean's 11 . The cast needed an ensemble of fresh A-list talent in order to match the heights of the original Rat Pack production, which starred Frank Sinatra , Dean Martin , and Sammy Davis, Jr. among others. But who was 2001's answer to the Rat Pack? George Clooney led the cast as the titular Danny Ocean, accompanied by love interest Julia Roberts , antagonist Andy Garcia, and heist partners Brad Pitt , Don Cheadle, and Matt Damon . This cast very nearly looked quite different, however.

"Steven had just done Erin Brockovich [also starring Julia Roberts] and Traffic [also starring Don Cheadle], and he was nominated for directing both films," Clooney recently recalled at 2023's TCM Film Festival. "So, people really wanted to work with Steven." As Soderbergh interjects though, "Some people did say no" to the production. "They did. Some very famous people told us to f— right off." Clooney then went on to name names, including his Three Kings co-star Mark Wahlberg and his fellow Robert Rodriguez collaborator Johnny Depp . "There were others. They regret it now." And rightly so, given the franchise's continuing popularity.

'Ocean's Eleven' Earned Itself Three Sequels

The film sees George Clooney's character assembling a team of the world's best thieves, whereas Clooney himself was trying to assemble a cast of the industry's brightest stars in order to rival the original. When sending Julia Roberts the script, Clooney recalls attaching a $20 bill and a note that said, "I hear you get 20 a picture now," referring to her $20 million-per-film rate. The joke landed and Roberts joined the cast. This playful wit translated well to the screen too, with the film turning out to be a major success. It received critical and commercial success, earning $450 million worldwide compared to its $85 million budget. This marked the biggest opening weekend for both Roberts and Brad Pitt, likely triggering regret in some actors who initially turned the film down.

It went on to warrant two sequels called Ocean's Twelve and Ocean's Thirteen , as well as a spin-off starring Sandra Bullock as Danny's sister Debbie who assembles her own all-female team in Ocean's 8 . The film was released in 2018, 11 years after we last saw Danny Ocean in Ocean's Thirteen . In it, Debbie frequently visits Danny's grave, alluding to Clooney's character having died off-screen between movies. "They killed me, by the way," joked Clooney. Soderbergh also joked at TCM Fest that he tried to soften the blow by taking two years off Clooney's age with the dates on the mausoleum, to which Clooney replied, "Sure, but I'm dead." Barbie 's Margot Robbie and Ryan Gosling are both attached to yet another Ocean's movie , currently in the works.

RELATED: 10 Iconic Roles That Almost Went To Other Actors

How Would Mark Wahlberg and Johnny Depp Have Fit Into 'Ocean's Eleven'?

Much like the 1960 original, Ocean's Eleven sees Danny Ocean (originally portrayed by Frank Sinatra) assembling a team of skilled thieves to pull off the simultaneous heists of several Las Vegas casinos. Danny enlists the help of his friend Rusty Ryan (Pitt) and former casino owner Reuben ( Elliott Gould ) to devise a plan before hiring the rest of the team; con men Frank ( Bernie Mac ) and Saul ( Carl Reiner ), auto specialists "the Malloy twins" ( Casey Affleck and Scott Caan ), explosives expert Basher (Cheadle), surveillance technician Livingston ( Eddie Jemison ), acrobat Yen ( Qin Shaobo ), and a young pickpocket named Linus (Damon).

According to Entertainment Weekly , Johnny Depp was offered the role of Linus, which eventually went to Matt Damon by way of Mark Wahlberg. The character served as the third lead, and the crew's new kid on the block, and although Wahlberg and Damon are both Bostonians of a similar age, Depp's casting in the role would have added at least seven years to the character. Depp may be harder to imagine as being interchangeable with Damon, but Wahlberg is often confused by fans as being Damon in real life, making their comparison more understandable. The two would eventually star alongside each other in Martin Scorsese 's The Departed , alongside Leonardo DiCaprio , whose refusal to play Eddie in Boogie Nights led to Wahlberg getting the star-making role. Everything comes full circle.

Owen Wilson, Ewan McGregor and the Coen Brothers Were Also Considered

George Clooney's commitment to Ocean's Eleven forced him to turn down the lead role in Unfaithful , so he understood why actors might have turned down the opportunity to join Ocean's Eleven . "It's also important to understand where we were at this time," he told EW . "The studios were making very big, broad, not very good films at the time. Steven had this idea of trying to infuse all of this independent film stuff that all of these young filmmakers were learning back into the studio system. It was going to get back to the things that they were doing from like 1964 to 1975." In looking to independent cinema, Clooney was interested in hiring Bottle Rocket 's Luke Wilson and Owen Wilson as the Malloy twins , but their commitment to The Royal Tenenbaums got in the way.

The roles of the Malloy twins were eventually considered for writer-directors Joel and Ethan Coen , who had recently worked with Clooney on O Brother, Where Art Thou? Soderbergh eventually cast Scott Caan and Casey Affleck as brothers in spite of the fact that Affleck is the real-life brother of actor Ben Affleck , with whom Matt Damon wrote and starred in Good Will Hunting . Bruce Willis was attached to star at one point , in a role later offered to Ewan McGregor . Ralph Fiennes was also attached to star , as was Mike Myers and Alan Arkin . Wahlberg was said to have dropped out in order to work on a different '60s remake, Tim Burton 's Planet of the Apes . Planet of the Apes was also the project that caused Tim Roth to turn down the role of Snape in Harry Potter .

In the end, once a film is shot, it's hard to imagine anyone in a role other than the actor whose performance is now immortalized in celluloid. It's fun to speculate, but given the success of Ocean's Eleven and the franchise as a whole, one can only assume that any other combination of talent might have jeopardized the end product. Johnny Depp and Mark Wahlberg may very well regret turning down the role of Linus in hindsight, but they've done extremely well for themselves in spite of it, regardless. Even George Clooney joked about his own regrets , rounding out his statement with an empathetic, "They regret it now. I regret doing f—ing Batman "!

Matt Damon Was the Third Choice for His ‘Ocean’s Eleven’ Role

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How Matt Damon became the chill cameo king of cinema

brad pitt and matt damon yacht

By Lucy Ford

Image may contain Matt Damon Matt Damon Matt Damon Electrical Device Microphone Purple Clothing Hat and Adult

Warning: mild spoilers for Drive-Away Dolls .

In 1997, Matt Damon landed comfortably into the A-list category for starring in (and winning an Oscar for writing) Good Will Hunting , and has stayed there ever since.

He's fronted his own action franchise (The Bourne series), earned prestige stripes in films like The Talented Mr. Ripley and The Martian and filled out a Roladex of frequent director collaborators that includes Spielberg, Soderbergh, Scorsese and Nolan . What we're saying is that Matt Damon is a big deal. One of cinema's biggest cheeses, if you will. He's the kind of star that can demand top billing or, at the very least, the coveted ‘And’ at the tail-end of an ensemble credits sequence. It's funny, then, that he's made a habit of volunteering himself up as a glorified bit-player in more films than most actors have film credits.

From Thor: Ragnarok to Confessions of a Dangerous Mind to the upcoming Coen brother (singular) film Drive-Away Dolls , he's not committed to the bit, he's committed to the business - the serious business, that is, of popping up as a cameo in his mate's films for three minutes before disappearing in a metaphorical puff of smoke (no seriously, almost all of his cameos seem to fall under the filmmaking equivalent of ‘cracking open a cold one with the boys’).

Where many actors of similar stature would turn their noses up to the prospect of a few minutes of sometimes-uncredited screentime, Damon seems to revel in it. Like the prospect of a blink-and-you'll-miss-it, ‘Was that who I think it was?’ appearance lights some kind of fire in him. Maybe that's why he does it so much.

Here are just some of the finest Matt Damon cameos in cinema, because he iconically has so many it's hard to rank them all.

8. Drive-Away Dolls (2024)

In the pantheon of Matt Damon cameos, his small appearance in Ethan Coen's lesbian road movie Drive-Away Dolls falls into the ‘expected’ category – he is in the trailer and his name is on the poster. What's unexpected about it, however, is the thimbles-worth of screentime he's given despite that. By our estimation, Damon racks up a max of five minutes of screen time in the film, and that includes a drive-by shot of him on a billboard and a surreal, de-aged sequence of him having sex with Miley Cyrus (yes, seriously).

Why did he do this?: The reason for this cameo seems pretty obvious: Damon starred in both Suburbicon and True Grit by the Coen Brothers, so for Ethan's first solo feature-film outing, he called on a gaggle of old faves.

7. Thor: Ragnarok (2017)

Thor's third film burst in like a huge sigh of relief, with Taika Waititi breathing new, goofy life into a superhero who, for the most part, had been weighed down by dull, deistic grandiosity. Damon's surprise bit-part that lasts no more than a minute comes in as a touch of light court entertainment, starring as an actor playing Tom Hiddleston's Loki in production aimed at entertaining the king (who is also secretly Loki). It's never not fun when actors poke fun at acting, even if it's taking place on a fictional Norse planet.

Why did he do this?: This is yet another case of a chill hang with the guys. “Chris (Hemsworth) just called me up, and Taika called me up, and I’m friends with those guys,” Damon has said about showing up as Asgaard's premiere Am-Dram performer.

6. Finding Forrester (2000)

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It's weird to say that, just three years after his big break, Matt Damon was already passing on the baton to a younger generation of prodigies, but that's exactly what his small cameo at the end of Finding Forrester conveys. Like Good Will Hunting , which made Damon a superstar, Finding Forrester follows an underprivileged student taken under the wing of a professor who sees his potential where others don't. Damon pops up at the end as an attorney tasked with telling the lead character Jamal (the Will Hunting proxy) that his mentor has passed and that he's included in the will. The short scene gives weight to the idea that once these films end, these characters' lives still go on.

Why did he do this?: Gus Vant Sant directed both Good Will Hunting and Finding Forrester , and Damon's cameo marks a trend of him popping up in his previous directors' later films.

5. Interstellar (2014)

Matt Damon's role in Christopher Nolan 's Interstellar is less of a cameo and more of a small but significant role that no one was expecting. In the run-up to the release, his name hadn't been announced, nor had any rumours of his involvement, so reaction to the moment his frozen astronaut is unzipped from a cryo-chamber and revealed elicited the kind of cinema-goer gasp that would make Tom Cruise 's toes tingle. Damon's appearance in Interstellar is important – almost as soon as he enters he's gone, but not before he betrays our flight crew and tries to leave them on a deserted ice planet. Nolan's choice of Damon is masterful because he understands the genial shorthand of him as a screen presence. Anyone not as instantly recognisable as trustworthy would have been a red herring from the start.

Why did he do this?: When Christopher Nolan calls, you answer.

4. Jay and Silent Bob Strike Back (2001)

The ‘actor pokes fun at his image by playing an asshole version of himself’ is a tried and tested (and always delightful) right of passage for many. Matt Damon's turn at the trend came in Jay and Silent Bob Strike Back, where he and Ben Affleck pretend to be shooting Good Will Hunting 2: Hunting Season . In between takes, they're pretentious and narcissistic, berating the crew and lamenting having to debase themselves with a crummy sequel. When police barge in mid-scene, Damon thinks Affleck has been caught soliciting sex workers again and sighs and says “Oh Jesus, again Ben?”. It's only about a minute, but they firmly solidify themselves as Hollywood's fave besties.

Why did he do this?: Kevin Smith, the Silent Bob of Jay and Silent Bob, was best friends with Ben Affleck after working together on Mallrats and Chasing Amy . Smith was actually the one who brought the script for Good Will Hunting to Miramax, who then famously went on to make it. Jay and Silent Bob Strike Back is essentially a big stew of all those things – the movie, Miramax, the enduring Affleck friendship – bubbling together.

3. Confessions of a Dangerous Mind (2002)

Matt Damon's cameo in Confessions of a Dangerous Mind is so blink-and-you'll-miss-it you'll still be saying “Wait, was that Brad Pitt ?” before you go “Wait, was that also Matt Damon?!”. Damon and Pitt star in George Clooney's directorial debut as two contestants on the 70s show The Dating Game , which was basically the same as Blind Date. The camera pans across the pair slowly, stopping for a fraction of a second on each of them as if Clooney is winking at you through the camera like ‘Yeah, that’s who you think it is.' They don't even have lines!

Why did he do this?: Simple – George Clooney . The pair had just starred together in Ocean's Eleven, marking the start of a decades-long collaborative friendship that's responsible for multiple films and the normalisation of movie stars playing pranks on each other.

2. Deadpool 2 (2018)

Matt Damon's cameo in Deadpool 2 isn't blink-and-you'll-miss-it, it's stare-at-the-screen-the-whole-time-and-have-no-idea-you're-watching-Matt-Damon. Even looking at the clip now, it's hard to believe anyone cottoned on to the fact he was in the film at all. Josh Brolin's villain Cable is introduced by landing on Earth next to two hicks talking about toilet paper on the back of a pick-up truck. Damon is in full hillbilly prosthetics, complete with long hair, beer belly, fake nose and trucker cap. He's zapped to death, ultimately, but his ‘Brendan Fraser in The Whale' -esque transformation lives on.

Why did he do this?: Ryan Reynolds may be coming for Damon's cameo crown (although his often comes with way more heavy a wink and a nudge), the pair joined forces thanks to Damon's relationship with Deadpool director David Leitch, who frequently used to act as his stuntman before jumping behind the camera.

1. Eurotrip (2004)

In the canon of Matt Damon cameos, there's no better, more baffling, more bewildering and more beautiful one than his random appearance in the interrailing sex comedy Eurotrip . He drops in as the lead singer of a pop-punk band singing about all the ways he boned a girl behind her boyfriend's back, and from the shaved head to the fake tattoos to the spiked labret chin piercing, it's about as un-Damon as you can get. For someone who, at that point, literally had an Oscar to his name, Eurotrip , a film that involves Zena Warrior Princess sodomising someone in an Amsterdam sex club and fraternal twins making out, seems pretty low-brow. But you sit there and tell us that the way he commits to the bridge lyric “I did her on his birthday” isn't award-worthy in itself.

Why did he do this?: He was just there. No, literally. He was in Prague filming The Brothers Grimm , and he was college buds with the writers of Eurotrip who were also making their movie there. So he got the clippers out, and the rest is cinema history.

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How Matt Damon Became the Chill Cameo King of Cinema

brad pitt and matt damon yacht

By Lucy Ford

Image may contain Matt Damon Matt Damon Matt Damon Electrical Device Microphone Purple Clothing Hat and Adult

Warning: This story contains mild spoilers for Drive-Away Dolls .

In 1997, Matt Damon landed comfortably into the A-list category for starring in (and winning an Oscar for co-writing) Good Will Hunting , and has stayed there ever since.

He's fronted his own action franchise (The Bourne series), earned prestige stripes in films like The Talented Mr. Ripley and The Martian, and filled out a Rolodex of frequent director collaborators that includes Spielberg , Soderbergh , Scorsese and Nolan . What we're saying is that Matt Damon is a big deal. One of cinema's biggest cheeses, if you will. He's the kind of star that can demand top billing—or, at the very least, the coveted “And” at the tail-end of an ensemble credits sequence. It's funny, then, that he's made a habit of volunteering himself up as a glorified bit-player in more films than most actors have film credits.

From Thor: Ragnarok to Confessions of a Dangerous Mind to the new Coen brother (singular) film Drive-Away Dolls , he's not committed to the bit, he's committed to the business—the serious business, that is, of popping up as a cameo in his mate's films for three minutes before disappearing in a metaphorical puff of smoke.

Where many actors of similar stature might turn their noses up to the prospect of a few minutes of sometimes-uncredited screentime, Damon seems to revel in it. Like the prospect of a blink-and-you'll-miss-it, wait-was-that-Matt-Damon? appearance lights some kind of fire in him. Maybe that's why he does it so much.

Here are just some of the finest Matt Damon cameos in cinema—because he iconically has so many it's hard to rank them all.

8. Drive-Away Dolls (2024)

In the pantheon of Matt Damon cameos, his small appearance in Ethan Coen's lesbian road movie Drive-Away Dolls falls into the “expected” category—he's in the trailer and his name is on the poster. What's unexpected about it, however, is that Damon racks up approximately five minutes of screen time in the film, maybe less. And that's counting a drive-by shot of him on a billboard and a surreal sequence in which a de-aged Damon has sex with Miley Cyrus (yes, seriously.)

Why did he do this?: The reason for this cameo seems pretty obvious: Damon starred in the Coen Brothers' True Grit and George Clooney's Coen-penned Suburbicon, so for Ethan's first solo feature-film outing, he called on a gaggle of old faves.

7. Thor: Ragnarok (2017)

Taika Waititi 's Thor film breathed new, goofy life into a superhero who, for the most part, had been weighed down by dull, deistic grandiosity. Damon's surprise bit part lasts no more than a minute; he plays an actor playing Tom Hiddleston's Loki in an entertainment meant to amuse the court of the king (who is also secretly Loki). It's never not fun when actors poke fun at acting, even if it's taking place on a fictional Norse planet.

Why did he do this?: For a chill hang with some bros, that's why. “Chris (Hemsworth) just called me up, and Taika called me up, and I’m friends with those guys,” Damon has said.

6. Finding Forrester (2000)

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It's weird to say that, just three years after his big break, Matt Damon was already passing on the baton to a younger generation of prodigies, but that's exactly what his small cameo at the end of Finding Forrester conveys. Like Good Will Hunting , which made Damon a superstar, Finding Forrester follows an underprivileged student taken under the wing of a professor who sees his potential where others don't. Damon pops up at the end as an attorney tasked with telling the lead character Jamal (this movie's Will Hunting figure) that his mentor has passed and that he's included in the will. The short scene gives weight to the idea that once these films end, these characters' lives still go on.

Why did he do this?: Gus Vant Sant directed both Good Will Hunting and Finding Forrester , and Damon's cameo marks a trend of him popping up in his previous directors' later films.

5. Interstellar (2014)

Matt Damon's role in Christopher Nolan's Interstellar is less of a cameo and more of a small but significant role that no one was expecting. In the run-up to the release, his name hadn't been announced, and no rumors of his involvement had leaked, so reaction to the moment his frozen astronaut is unzipped from a cryo-chamber and revealed elicited the kind of gasps from cinema-goers that would make Tom Cruise 's toes tingle. Damon's appearance in Interstellar is important— almost as soon as he enters he's gone, but not before he betrays Matthew McConaughey and crew and tries to ditch them on a deserted ice planet. Nolan's choice of Damon is masterful because he understands the genial shorthand of him as a screen presence. Anyone not as instantly recognizable as trustworthy would have been a red herring from the start.

Why did he do this?: When Christopher Nolan calls, you answer.

4. Jay and Silent Bob Strike Back (2001)

Poking fun at your image by playing an asshole version of yourself is a tried and tested (and almost always delightful) right of passage for many an actor. Matt Damon got his chance in Jay and Silent Bob Strike Back, where he and Ben Affleck pretend to be shooting Good Will Hunting 2: Hunting Season . In between takes, they're pretentious and narcissistic, berating the crew and lamenting the crummy sequel with which they've debased themselves. When police barge in mid-scene, Damon thinks Affleck has been caught soliciting sex workers again and sighs and says “Oh, Jesus—again, Ben?” The scene only lasts about a minute, but they firmly solidify themselves as Hollywood's fave besties.

Why did he do this?: Kevin “Silent Bob” Smith was best friends with Ben Affleck, who he'd worked with on Mallrats and Chasing Amy . And it was Smith who brought the script for Good Will Hunting to Miramax, who then famously went on to make it. Jay and Silent Bob Strike Back is essentially a big stew of all those things—the movie, Miramax, the enduring Affleck friendship – bubbling together.

3. Confessions of a Dangerous Mind (2002)

Matt Damon's cameo in Confessions of a Dangerous Mind is so blink-and-you'll-miss-it you'll still be saying “Wait, was that Brad Pitt ?” before you go “Wait, was that also Matt Damon?!”. Damon and Pitt star in George Clooney's directorial debut as two contestants on The Dating Game , which was basically a ‘70s version of Blind Date. As the camera pans across the pair slowly, pausing on each of them for a fraction of a second, it’s as if Clooney is winking at you through the camera, chuckling “Yeah, that’s who you think it is.” They don't even have lines!

Why did he do this?: Simple— George Clooney . The pair had just worked together on Steven Soderbergh's Ocean's Eleven, kicking off a decades-long collaborative friendship that's responsible for multiple films and the normalization of movie stars playing pranks on each other.

2. Deadpool 2 (2018)

Matt Damon's cameo in Deadpool 2 isn't blink-and-you'll-miss-it—it's stare-at-the-screen-the-whole-time-and-have-no-idea-you're-watching-Matt-Damon. Even looking at the clip now, it's hard to believe anyone cottoned on to the fact he was in the film at all. The scene introduces Josh Brolin's villain Cable, who lands on Earth next to two hicks on the back of a pickup truck, having a conversation about toilet paper. Damon is in full hillbilly prosthetics, complete with long hair, beer belly, fake nose and trucker cap, and while he's soon zapped to death, his Brendan-Fraser-in- The-Whale -worthy transformation is indelible.

Why did he do this?: Presumably as a favor to Deadpool director David Leitch, who worked with Damon on a couple of Bourne films in his former life as a stunt performer.

1. Eurotrip (2004)

In the canon of Matt Damon cameos, there's no better, more baffling, more bewildering and more beautiful one than his random appearance in the train-based sex comedy Eurotrip . He drops in as the lead singer of a pop-punk band singing about all the ways he boned a girl behind her boyfriend's back, and from the shaved head to the fake tattoos to the spiked labret chin piercing, it's about as un-Damon as you can get. By this point he was already Academy Award winner Matt Damon , and you wouldn't necessarily expect to run into him in a film that involves Xena Warrior Princess sodomizing someone in an Amsterdam sex club and fraternal twins making out. But you sit there and tell us that the way he commits to the lyric “I did her on his birthday” isn't Oscar-worthy in itself.

Why did he do this?: He was just there. No, literally. He was in Prague filming The Brothers Grimm , and he was college buds with the writers of Eurotrip, who were also making their movie there. So he got the clippers out, and the rest is cinema history.

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George Clooney, Brad Pitt and Matt Damon to ‘reunite for new Ocean’s movie’ 15 years after the last film

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George Clooney , Brad Pitt and Matt Damon are set to reunite for another instalment of the Ocean’s franchise 15 years after the last film, according to reports.

The Hollywood stars will join forces once again for Ocean’s 14 after previously vowing Ocean’s 13 would be their last movie in the series.

According to The Sun , a source said: “Rumours of a film starring George, Brad and Matt have swirled for years but the timing was off and their jam-packed schedules meant that it was just not possible.

“Finally the right team for the job has come together in a bid to make it a huge success and the main stars thought it would be good fun to revisit.

“The franchise is hugely popular and the brilliant storyline was an opportunity that was too good to miss.”

The Evening Standard has contacted representatives for Brad Pitt, George Clooney and Matt Damon for comment.

Ocean’s Eleven kicked off the film franchise and centred on Danny Ocean (George) and Rusty Ryan (Brad) as they planned a $160 million heist from casino owner Terry Benedict (Andy Garcia), the lover of Danny’s ex-wife Tess ( Julia Roberts ).

Released in 2001, the movie made a whopping $450million at the box office and was followed by two sequels, 2004’s Ocean’s Twelve and Ocean’s Thirteen in 2007.

In 2018, the film inspired spin-off Ocean’s Eight with an all-female cast lead by Oscar winners Sandra Bullock and Cate Blanchett.

Previously Don Cheadle , who plays Basher Tarr in the films, spoke how plans to make an Ocean’s 14 were axed following the death of fellow cast member Bernie Mac in 2008.

Cheadle said at the time: “We were talking about it, and then Bernie passed, and very quickly we were like, ‘No, we don’t want to do it.’”

Although filming plans were put on ice, Damon expressed interest in another film last year but said the future of the franchise was up to its director Steven Soderbergh after two of the original cast have passed away, Carl Reiner and Mac.

Speaking on Good Morning America, he shared: “It would always be up to Steven Soderbergh if there was a story.

“We have lost a couple of our members, so we would have to figure it out, we are a depleted gang now.”

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Minnie Driver Reveals the Advice She'd Give Her Younger Self After Matt Damon Split

Minnie driver reflected on her reaction to seeing ex matt damon and ben affleck win the screenplay oscar for good will hunting in 1998 and what she wishes she could tell herself back then..

Minnie Driver is sending her younger self some goodwill.

The Good Will Hunting actress recently shared insight into what it was like seeing her reaction to ex Matt Damon  winning the  Oscar  for writing the 1997 film and revealed what she wishes she could've told herself back then.

"First of all, I want to wrap my arms around that young woman and hug her and go, 'It's all going to be fine, honey. Don't worry,'" Minnie said on the March 14 episode of The Jennifer Hudson Show . "We'd recently broken up. I was nominated, he was nominated, the movie was so amazing, he had a new girlfriend. I was totally heartbroken."

Being in the public eye, she couldn't navigate that heartache with total privacy.

"Anyone who's been heartbroken can understand," she shared, "it's like the last thing you want is everybody having a window in on that and it was so public."

And while Academy Awards viewers may witnessed her pain on screen when Matt and Ben Affleck  won the original screenplay prize during the 1998 ceremony, Minnie said she'd only recently seen the video of her watching the pair take the stage .

"I hadn't seen the clip—I don't know that I'd ever seen it," the 54-year-old, who was also nominated for her supporting role in Good Will Hunting , explained. "I'd never seen my face—the reaction when they won. And they cut to me 'cause it was a camera right in the face of the poor, young, 25-year-old girl who's about to burst into tears."

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So Minnie's comment —in which she recalled being "devastated"  and noted Matt had broken up with her only weeks before—was in response to the "raw and vulnerable" moment. And if the Circle of Friends star could go back in time, she'd tell herself everything would be OK.   

"From this vantage point—you know, 20/20 vision much later in my life," she added, "I wish I could have told her, ‘Honey, it's cool. Like you can celebrate, and life's gonna be great, and beautiful, and hard and amazing. And you're gonna love again. It'll be fine.'"

Still, Minnie indicated she would have appreciated a little more empathy from the public at the time.

"A heartbreak is private," she noted. "And then if you're an actress, it can be very public. So maybe just us all relating to each other a bit more as humans and we have these similar experiences through different lenses—perhaps we can treat each other all a bit more kindly."

To see more celebrity relationships you may have forgotten about, keep reading.

They played doomed lovers twice, in 1990's Too Young to Die? and 1993's  Kalifornia , but in real life they had a perfectly lovely relationship .

"I still love the woman," Pitt, who was Lewis' date to the 1992 Oscars when she scored a Supporting Actress nomination for  Cape Fear , told Vanity Fair in February 1995. "There's some real genius there. I had a great time with her...It was one of the greatest relationships I've ever been in. The problem is, we grow up with this vision that love conquers all, and that's just not so, is it?"

It wasn't just a Gen X fever dream, they really closed out the 20th century as a couple after, legend has it, being introduced by Gwyneth Paltrow   (who famously dated Damon's best bud Ben Affleck ). They split up in 2000.

After the fact, Damon called Ryder a "great woman" in a 2004 Playboy  interview , while Ryder told Black Book in 2009, "Matt couldn't be a greater, nicer guy. I'm really lucky that I'm on good terms with him."

There was something about their chemistry at the 2003 Nickelodeon Kids' Choice Awards, where Diaz presented Timberlake with the award for Best Burp—because they dated for almost four years, seriously enough to issue a statement when their relationship ended in 2007, "mutually and as friends, with continued love and respect for one another."

The  Scandal  star appeared on the cover of  InStyle Weddings  in 2005 when she was engaged to the  Big  actor , but they split up in 2007.

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After her divorce from Ryan Phillippe and before marrying agent Jim Toth , Reese starred with Jake in the 2007 thriller  Rendition  and they dated for a couple of years.

"She is, as I would say about most of the women who I'm close friends with or had relationships in my life," Jake said admiringly of his ex , "one of the smartest, strongest people I've ever met."

Before marrying  Livia Giuggioli  in 1997 (they separated in 2019), Firth had a five-year relationship with Tilly that produced son William Joseph Firth , who was born Sept. 20, 1990. The younger Firth is also an actor who appeared with his father in  Bridget Jones's Baby .

This was them: The U.S. Open champ courted the A Walk to Remember  star between 2003 and 2004, but ultimately it wasn't a love match .

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You can't blame the  Mad Men  star for liking funny guys . Jones and Sudeikis dated for a few months in 2010, five years before she briefly dated Will Forte .

The  Good Will Hunting  stars paired off in real life, too, but they didn't drive off into the sunset together .

"Well, I'm single," Damon said on  The Oprah Winfrey Show  in January 1998. "I was with Minnie for a while, but we're not really romantically involved anymore. We're just really good friends, and I love her dearly….I care about her a lot. We care about each other a lot. It wasn't meant to be, you know? And if it's not meant to be, then it's not meant to be."

The pronouncement was a bit too public for Driver's taste. "It's unfortunate that Matt went on Oprah ," she told the  LA Times later that year. "It seemed like a good forum for him to announce to the world that we were no longer together, which I found fantastically inappropriate."

The stars met on the set of the 1981 movie  Excalibur  and eventually lived together (Neeson says Mirren gave him his first driving lessons) before they broke up in the mid-'80s.

"I should be so lucky and be honored to have spent three or four years with that lady," Neeson told  ET Canada  in February 2023. "She's really something else."

Finding love in Jurassic Park ? Talk about a meat cute.

The co-stars began dating after filming the 1993 blockbuster , with Goldblum telling The Chicago Tribune at the time, "I was struck, I'd been a big fan of hers. I think she's an amazing actress, and a spectacular person. I was struck from the beginning. But after the movie we realized we liked each other."

They got engaged in 1995 but ultimately split two years later. They reunited on-screen for the first time in 2022's  Jurassic World: Dominion , the sixth installment in the franchise.

The X-Files alum was in a relationship with  The Crown  creator between 2016 and 2020. Anderson won an Emmy for her turn as  Margaret Thatcher in the Netflix hit in 2020.

According to Arquette, the two dated while filming their 1995 Western Wild Bill .

The  Clueless actor confirmed a little-known rumor during a  Reddit AMA chat in November 2015, revealing that he used to date the actress. The two had starred in the 1992 TV movie  Desperate Choices: To Save My Child .

"She was my first actress girlfriend," he said. "We had a long distance relationship for a long time. I was so into her."

E! News exclusively broke the news that the Real Housewives of New York star and Modern Family actor were a pair in 2015. But by the following year, they had split. 

The Southland  alum and the actor, who played Theo Huxtable on The Cosby Show , dated for several years before calling it quits in 2013.

The famous bachelor was actually settled in with Preston pre- John Travolta back in 1987. They even lived together and shared a potbellied pig named Max before breaking up in 1989.

Why, yes, she does believe in life after love. The Top Gun star and the legendary diva dated back in the '80s following her divorces from Sonny Bono and Gregg Allman . 

Before he was Heidi Klum 's ex, the "Kiss from a Rose" musician romanced a different supermodel.

The duo reportedly started dating after meeting on the set of the 2005 film Brick , but they only stayed together for six months.

The Dawson's Creek alum and the Josie and the Pussycats star dated for about a year back in 2002.

The NCIS: LA stud and America's sweetheart dated way back in 1993, when 17-year-old Witherspoon first moved to Los Angeles.

The man who now rocks the Iron Man suit for Marvel admitted that drugs and alcohol were to blame for the end of his seven-year relationship with the Sex and the City star. "I liked to drink, and I had a drug problem, and that didn't jibe with Sarah Jessica," he admitted in an a 2008 interview with Parade , "because it is the furthest thing from what she is. She tried to help me. She was so miffed when I didn't get my act together."

The Friends alum and The Hangover star supposedly had a fling 2003, but it didn't last long enough to be more than a little blip on the Hollywood hookup radar.

The 2 Broke Girls actress dated her Thor costar briefly in 2010, appearing very cozy while attending Comic-Con to promote the Marvel film. But their relationship fizzled by the time the movie premiered the following year.

In 1999, way before he wed Blake Lively , Reynolds dated the 3rd Rock From the Sun star. The duo even attended the premiere of  The Green Mile together.

The child actors turned A-listers briefly dated in 2006 but remained close friends—and co-starred in the intense 2009 drama  Brothers .

"She's a vegan," Gyllenhaal pointed out when presenting Portman with the Desert Palm Achievement Award in 2011, "which makes it really frustrating when you're picking a place to eat."

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The True Story Behind The Epic 'Wounded Letter' Prank George Clooney Played On Tina Fey And Amy Poehler, And How Matt Damon Totally Got Roped In

Nobody loves a prank like George Clooney!

George Clooney in Ticket to Paradise, Tina Fey in 2024's Mean Girls, Matt Damon in Ford Vs Ferrari (side by side)

It's awards season, meaning award show junkies can look forward to many comedic monologues starting off the many star-studded ceremonies. Hosts come and go, but we will never forget when Tina Fey and Amy Poehler hosting the Golden Globes together was a regular thing . They were fantastic, always making audiences howl with laughter before the awards were given out. However, one year, a joke directed at George Clooney got them involved in a hilarious prank war with the movie star, and somehow, he found a way to rope his pal Matt Damon into the whole thing. 

The Jokes Amy Poehler And Tina Fey Made At The 2014 Golden Globes

Fey and Poehler are considered some of the best Golden Globes hosts of all time, and they got that reputation for a reason. Not only do they have impeccable chemistry and stage presence, but also know how to make a hilarious joke aimed at movie stars. At the 2014 Golden Globes , the SNL alumni decided to make a silly jab at Matt Damon for his role in Behind the Candelabra , a TV movie for HBO subscribers . They joked:

Matt Damon is here for 'Behind the Candelabra.' Matt, on any other night, in any other room, you would be a big deal, but tonight, and don't take this the wrong way, you're basically a garbage person.

The joke got a big laugh, and highlighted the large amount of A-list talent in the room. The funny ladies additionally made a joke about George Clooney , and his brief role in 2013’s Gravity . They said:

[Gravity is] the story of how George Clooney would rather float away into space and die than spend one more minute with a woman his own age.

The joke also was met with a strong postive reception, including from Clooney himself, who famously has a great sense of humor and can make a joke at his own expense. It was a nod to his “forever bachelor” image, which he held for a while before he wed Amal Clooney in 2014. Even though Clooney seemed to think the joke was funny, he still wanted to get Poehler and Fey back in his own way, and pulled a prank on the two co-hosts, using the joke about his friend Matt Damon as fuel. 

How George Clooney Plotted And Executed His Revenge

Clooney is famous for his practical jokes, so a prank response was expected from the actor. He once left Matt Damon and Don Cheadle stranded at a haunted house, and even pranked Richard Kind into thinking his cat was chronically constipated. But this prank on Poehler and Fey may have been his best yet. In an interview with Sirius XM radio, the Michael Clayton star explained that he got the Sisters stars back by obtaining stationary made with Matt Damon’s name on it, and wrote a note to the comedians pretending to be the famous Good Will Hunting actor. He said: 

I sent [Tina Fey] a letter going ‘Dear Tina… listen…” And it [says it’s] from Matt. It just says, ‘Look it sounds hypocritical ‘cause I laughed at the jokes about George and Leo, but that’s sort of what people think about them. But when you call me a garbage man, it just sounds like low hanging fruit. It sounds like an easy joke and I don’t want an apology or anything else. I just want you to know that my kid now calls me the garbage man, so I just wanted you to know how I felt.

This was a hilarious move, and even more funny knowing that George Clooney had to go the extra mile and get that stationary custom made. He decided not to let Damon in on the joke, either, so the actor had no idea that his Ocean’s 11 co-star decided to rope him into his schemes. The Jason Bourne star may have been an innocent victim of the practical joke, but this somehow makes it funnier. 

How Tina Fey And Amy Poehler Responded To Matt Damon

Of course, all parties had to have figured out that George Clooney was pranking them eventually. Luckily, Amy Poehler and Tina Fey seemed to figure out by how the letter was written that something was off. The Damon joke was very mild, and the Boston-born actor has a great sense of humor. Tina Fey told Good Morning America (via Wonderwall ) that after receiving the letter, they decided to send Matt Damon apology fruit baskets, while also telling him that they suspected George Clooney was pranking them. 

When Damon received this massive gesture from the comedians, he was understandably confused. After reading the letters attached to the fruit baskets, it became very clear that he was being pranked, and the culprit was very obvious. He told the story from his perspective on The Late Show with David Letterman , saying:

I get these two fruit baskets, the size of your desk. I’m not [kidding], they are the biggest things I’ve ever seen. One says ‘Letter #1’ with an envelope attached, and one says ‘Letter #2’ with an envelope attached. I opened letter number one and it’s this apology from Tina and Amy saying ‘We really thought you could take a joke, you know we’re sorry we hurt your feelings.’ And then I open ‘Letter #2’ […] and ‘Letter #2’ says, ‘Dear Matt, if your note is part of some George Clooney prank, as I strongly suspect it is, you A-list amateurs are going to have to step it the f- up. We are not some easily confused starlets you’re dealing with here. We are grown ass professional comedians!’

Fey and Poehler must’ve assumed Matt Damon was in on the joke, but this token of “sincerity” was the first the actor had heard of it. He realized pretty quickly what had happened, and that Clooney made stationary impersonating him. He technically had it coming, considering he helped Brad Pitt play a prank on Clooney while filming in Italy . The whole thing is hilarious, and the way the comic duo responded made the whole thing even funnier. I hope Damon was able to get through all the fruit. 

It seems like the pranks from Clooney have slowed down over the years, however Matt Damon did mention the actor's love for practical jokes when honoring Clooney at the Kennedy Center . All four of these actors are absolutely hilarious, and I never get tired of this story. Clooney famously is unbeatable when it comes to these antics, but in 2014, he finally met his match with Amy Poehler and Tina Fey. 

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brad pitt and matt damon yacht

Matt Damon cuts a relaxed figure in a white shirt as he heads out on a boat on day four of Cannes Film Festival

By Ella Hodson For Mailonline

Published: 20:27 EDT, 9 July 2021 | Updated: 20:37 EDT, 9 July 2021

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Matt Damon looked relaxed as he headed out on a boat at the 74th Annual Cannes Film Festival on Friday. 

The actor, 50, wore a white shirt and black sunglasses as he joined a group of friends to sail on the mediterranean sea. 

The star wore beige chinos and a beige polo top with black trainers and he enjoyed some downtime from the event. 

Chilled: Matt Damon, 50, looked relaxed in a white shirt as he headed out on a boat at the 74th Annual Cannes Film Festival on Friday

Chilled: Matt Damon, 50, looked relaxed in a white shirt as he headed out on a boat at the 74th Annual Cannes Film Festival on Friday

He has been attending the star-studded festival ahead of the release of his new film Stillwater.

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The new thriller flick Stillwater, is about a man who travels from Oklahoma to France to help his estranged daughter, as she is in prison for a murder she says she didn't commit. 

This outing comes as he was in high spirits at a photo call for the new film with his co-star, Camille Cottin.  

On the water: The actor wore a white shirt and black sunglasses as he joined a group of friends to sail on the mediterranean sea

On the water: The actor wore a white shirt and black sunglasses as he joined a group of friends to sail on the mediterranean sea

Stylish: He has been attending the star-studded festival ahead of the release of his new film Stillwater

Stylish: He has been attending the star-studded festival ahead of the release of his new film Stillwater

The duo celebrated positive reviews with their co-stars after the crime drama movie was met with a standing ovation following its premiere screening the night before.

Meanwhile, actress Marion Cotillard cut a chic figure as she stepped out at the festival.

The beauty looked relaxed in a white cropped T-shirt and light blue jeans while out and about at the festival.  

Happy days: Matt and co-star Camille Cottin put on a jovial display as they attended a photocall for the new film Stillwater during the 74th annual Cannes Film Festival in France on Friday

Happy days: Matt and co-star Camille Cottin put on a jovial display as they attended a photocall for the new film Stillwater during the 74th annual Cannes Film Festival in France on Friday 

 She looked glowing as she wore her sleek raven tresses in a side parting around her shoulders, and wore retro-style sunglasses which framed her face. 

She held a dark green bomber jacket in her hand and paired the look with bright purple stilettos.   

The Inception star has been attending the event ahead of the release of her new film  in the upcoming musical film Annette alongside Adam Driver, which is being screened at the festival.

Effortlessly chic: Meanwhile, actress Marion Cotillard cut a stylish figure as she stepped out at the festival. The beauty looked relaxed in a white cropped T-shirt and light blue jeans while out and about at the festival

Effortlessly chic: Meanwhile, actress Marion Cotillard cut a stylish figure as she stepped out at the festival. The beauty looked relaxed in a white cropped T-shirt and light blue jeans while out and about at the festival

The film tells the story of a provocative stand-up comedian (Driver) and his wife, a world-famous soprano (Cotillard). 

Their glamorous life takes an unexpected turn when their daughter Annette is born, a girl with a unique gift. 

It marks French filmmaker Leos Carax first feature film since the critically-acclaimed 2012 film Holy Motors for this new musical. 

Beautiful: She wore her sleek raven tresses in a side parting around her shoulders, and wore retro-style sunglasses which framed her face

Beautiful: She wore her sleek raven tresses in a side parting around her shoulders, and wore retro-style sunglasses which framed her face

New film: The Inception star has been attending the event ahead of the release of her new film in the upcoming musical film Annette alongside Adam Driver, which is being screened at the festival

New film: The Inception star has been attending the event ahead of the release of her new film in the upcoming musical film Annette alongside Adam Driver, which is being screened at the festival

Dramatic: Annette documents the story of an opera singer and her husband coming to terms with their life after welcoming their first child together

Dramatic: Annette documents the story of an opera singer and her husband coming to terms with their life after welcoming their first child together

Share or comment on this article: Matt Damon looks relaxed as he heads out on a boat on day four of Cannes Film Festival 

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Brad Pitt, Leonardo DiCaprio and Matt Damon

Brad Pitt, Leonardo DiCaprio and Matt Damon turned down Brokeback Mountain

The movie could have looked very different

It is sometimes difficult to imagine a film in any other way than how it ended up, especially when they are as successful as Brokeback Mountain , but the movie could actually have turned out very differently. Gus Van Sant – the Oscar-winning director behind the likes of Good Will Hunting – was initially offered to direct Brokeback Mountain and has spoken out about who he wanted to cast for the movie.

"Nobody wanted to do it," Van Sant said. "I was working on it, and I felt like we needed a really strong cast, like a famous cast. That wasn’t working out. I asked the usual suspects: Leonardo DiCaprio, Brad Pitt, Matt Damon, Ryan Phillippe. They all said no."

Brokeback Mountain

Van Sant admitted that his struggle to nail down any of the stars he had wanted eventually ended up in him moving away from the movie.

"What I could have done, and what I probably should have done, was cast more unknowns, not worried about who were the lead actors. I was not ready. I’m not sure why. There was just sort of a hiccup on my part. There was something off with myself, I guess, whatever was going on."

Of course, in the end, the movie was directed by Ang Lee with the lead roles going to Jake Gyllenhaal and Heath Ledger – and Brokeback Mountain went on to win three of the eight Oscars that it was nominated for.

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Matt Damon: 'I spend my life trying to be like Brad Pitt'

Bad news for the residents of New York City: After many years of making it his home, Matt Damon is packing up and moving his family to Los Angeles. But the TODAY anchors wanted to see if they could entice him to stick around a little longer when he visited on Tuesday, even suggesting he'd be a great mayoral candidate.

"Basically all of our friends with little kids are out there," said Damon. "We're a little conflicted. We love it here, we're really happy here and New York will always be here. It might just turn out to be a little jaunt out there and then a return.... It's hard to leave here."

Later on, however, he got down to business with Lauer and discussed his new sci-fi action film, "Elysium," which was directed by "District 9's" Neill Blomkamp. It takes place in a futuristic world where Earth is a third-world country and the "haves" live on a rotating space station called Elysium, but while it has "cool resonant themes," said Damon, it's not meant to rabble-rouse.

"Neill, the director, would just go crazy if he thought anybody was saying it was a 'call to action,'" he said. "All he really wants to do is make up the most entertaining ... sci-fi movie that he can."

One last matter: Lauer brought up an interview in which Damon suggested that his frequent co-star Brad Pitt was actually envious of him. Damon explained the envy actually came from the fact that he could walk with his kids in New York and not be assailed by photographers, unlike Pitt.

"What else would it be?" laughed Damon. "I spend my life trying to be like Brad Pitt."

Elysium opens in theaters on Aug. 9.

‘Deadpool 2’: How an Actor Who Was Nearly Cable Ended Up with an Unforgettable Cameo

Ryan Reynolds and director David Leitch talk about those two huge A-List cameos in the sequel.

Spoilers for Deadpool 2 follow below.  

Leave it to the Deadpool franchise to waste the biggest movie stars in the world. Indeed, if you’ve seen Deadpool 2 you may or may not know that Brad Pitt and Matt Damon have cameos in the film—one is insanely brief, and another has the actor covered in prosthetics to the point that he’s completely unrecognizable. Classic Deadpool .

Pitt plays X-Force member The Vanisher, and his cameo lasts about eight frames when the superhero hits an electrical wire. Damon, meanwhile, plays the fat redneck who happens upon Josh Brolin ’s Cable when his character arrives from the future. So when we caught up with Ryan Reynolds and director David Leitch , we had to find out how these cameos came to be, and what it took to make them happen.

When it comes to the Brad Pitt cameo, some fans may be aware that the actor was in early talks to potentially play Cable in the film, but the deal never came together. Leitch says that meeting went so well that it lead to Pitt’s cameo:

“I was ecstatic [about the Pitt cameo], I couldn’t believe it. We had early talks with him about Cable, you remember the artwork was leaked and we had to pull it back from the internet. It was serious talks and I think he was really interested, he loves the universe and he loves Deadpool. But for whatever reason it didn’t work out, and he kind of left the door open when we left that meeting, like, ‘If you guys ever need anything give me a call, I’d love to be involved,’ and Ryan just said, ‘Oh I have an idea.’ So we started to think about what it could be and The Vanisher thing was perfect.”

Reynolds revealed that Pitt was paid for his cameo with a single cup of coffee:

“I can confirm that that is Brad Pitt. I still don't even know how we got him for the movie. I just wrote him a letter and explained what it was we were doing and the sort of premise behind it was, ‘What's the most wasteful way to use the biggest movie star in the world?’, and it was through a character that is largely invisible and worthless throughout the movie. Then just having him show up for eight frames of footage, I guess Brad found that funny, we all found that funny. And he said, yes and the next thing you know he came and shot for about seven minutes. It took him longer to drink the coffee that he requested as payment than to shoot the cameo. He’s such a gentleman, and such a funny, charming human being, and probably the biggest movie star on earth. That was pretty exciting for all of us.”

But while Pitt was considered for the role of Cable, Leitch says he can’t imagine anyone other than Brolin in the role now:

“It always works out, and now I can’t see it any other way. That’s sort of how casting goes, I mean you start down this road and you work with actors and you’re trying to find the right person for the role, and then you just land this person that’s perfect, it’s serendipitous.”

And Brolin has a bit of a True Grit reunion in his cameo with Matt Damon, which Leitch says came about because of the actor's friendship with Ryan Reynolds:

“[The cameos happened] because you have the celebrity star-power of Ryan Reynolds, you have a franchise that is beloved, and then I have worked with both of them as a stunt double, so I think having all of those things helped. Moreso Ryan Reynolds and moreso Deadpool being beloved, but me knowing who they were cracked the door open a bit, and actually Matt knows Ryan really well too.”

Indeed, Reynolds merely asked Damon to make a cameo while they were having dinner:

“The Matt one came from Ryan just having dinner with Matt and he was telling him about the gag and was like, ‘Would you want to do it?’ It was that simple. I don’t even know if Matt knew I was directing the movie at the time.”

Then came the decision to shroud the cameo in secrecy by putting Damon in full prosthetic makeup, to the point that the crew didn’t even know it was him:

“Bill Corso, our makeup artist, he’s a master at prosthetics. He had Matt in the chair for three hours, and a lot of the crew didn’t know. There were some people who had worked with him on movies, and if you’re on a run of a show of a movie you’ve worked with him for four months, you look at him every single day. But we didn’t even tell the crew, his name wasn’t on the call sheet—it was a fake name. Nobody really knew what that scene was about, they were like, ‘Why are we shooting these two rednecks?’ We just didn’t tell anybody.”

And indeed most fans didn’t even recognize it was Damon until his cameo was revealed by writers  Rhett Reese  and  Paul Wernick . So yeah, it’s oh-so-very  Deadpool  to have two of the biggest movie stars in the world in this movie in ways that are almost delightfully wasteful of their talents.

For more on  Deadpool 2 , peruse links to our recent articles below:

  • Here's How That 'Deadpool 2' Post-Credits Scene Happened & What Didn't Make the Cut
  • 'Deadpool 2': Ryan Reynolds and David Leitch on If [SPOILER] Is Really Dead
  • 'Deadpool 2': Let's Talk about That Marvel Supervillain Cameo
  • Exclusive: Ryan Reynolds Gives an ‘X-Force’ Update and Talks about the Film’s Rating

Brad Pitt and Leonardo DiCaprio say they both get mistaken for Matt Damon by fans, and Pitt has even signed their autographs

  • Leonardo DiCaprio and Brad Pitt both get mistaken for Matt Damon, the pair confirmed in an interview with BBC Radio 1.
  • "I may have even gotten a Brad Pitt once," DiCaprio told the interviewer.
  • Instead of letting the fans down gently, Pitt said he prefers to keep them in blissful ignorance and sign an autograph on Damon's behalf.
  • "They'll figure it out later," Pitt said.
  • Watch the interview in full below.
  • Visit INSIDER's homepage for more stories.

Insider Today

If you think you met Matt Damon recently, you might want to check whether that autograph is the real deal.

In an interview with BBC Radio 1's Film Critic Ali Plumb  and their "Once Upon A Time In Hollywood" costar Margot Robbie, Brad Pitt and Leonardo DiCaprio revealed that they both get mistaken for an unlikely fellow A-lister: Matt Damon.

"I get Matt Damon," DiCaprio told Plumb, to which Pitt chipped in: "I get Matt!"

Read more: Jimmy Kimmel said his staffers were too scared of Quentin Tarantino to eat popcorn when they watched 'Once Upon a Time in Hollywood' with him

As well as being three of Hollywood's biggest leading men for decades now, both DiCaprio and Pitt have worked with Damon in the past — DiCaprio in "The Departed" and Pitt, of course, in the "Oceans" saga — which may explain the confusion.

"I may have even gotten a Brad Pitt once," DiCaprio added.

"You can't be mad about that," Robbie chimed.

"You can't be mad about any of them," DiCaprio agreed.

Robbie then said she recently got mistaken for her lookalike actress Emma Mackey, who stars in the Netflix series "Sex Education."

Robbie said she let the fans down gently and told them that she was not, in fact, in "Sex Education," and that they had her confused.

Pitt, it seems, likes to take a different approach.

"I've actually signed autographs as Matt," he said.

Gesturing a random squiggle with his hand, Pitt confirmed that he just made a signature up for his colleague: "They'll figure it out later."

"Yeah, why ruin their day? Why ruin the moment?" Robbie said.

Watch the interview in full below:

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COMMENTS

  1. Ocean's Eleven

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