George Clooney and Brad Pitt have often shared the screen together throughout their careers, bringing their real-life friendship into their work. The duo famously starred in Steven Soderbergh’s Ocean’s trilogy together, but this isn’t their only collaboration. They have also worked together on a documentary, a televised play, and some other critically acclaimed movies. In 2024, Clooney and Pitt led the cast of Wolfs, a crime movie by Jon Watts that features the two stars as lone fixers tasked with the same job, forcing them to work together.
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It’s been 17 years since Clooney and Pitt signed off from the Ocean’s franchise, but Clooney recently announced in press for Wolfs that Ocean’s Fourteen is currently being developed in very early stages. While that doesn’t confirm it will happen, it shows that Clooney and Pitt are still interested in collaborating more. Not to mention, a Wolfs sequel seems to be in development at Apple TV+, with both stars and the director hoping to return.
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9 IF (2024)
George Clooney Plays Spaceman & Brad Pitt Plays Keith
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IF
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*Availability in US Director John Krasinski Release Date May 17, 2024 Cast Ryan Reynolds , John Krasinski , Cailey Fleming , Steve Carell , Matt Damon , Emily Blunt , Phoebe Waller-Bridge , Vince Vaughn , Sam Rockwell , Maya Rudolph , Jon Stewart , Awkwafina
Brad Pitt is listed in the credits for IF, so he is technically one of Clooney’s co-stars, but the truth isn’t so straightforward. George Clooney voices Spaceman, an imaginary friend with the appearance of an astronaut, possibly as a subtle reference to his role in Gravity. Brad Pitt’s role in IF is much weirder. He is credited as Keith, a silent and invisible imaginary friend with a habit of tripping Ryan Reynolds’ character. The character of Keith is a reference to Brad Pitt’s cameo in another Ryan Reynolds movie. He plays Vanisher in Deadpool 2, an invisible superhero who shows his face for a split second.
Brad Pitt is listed in the credits for
IF,
so he is technically one of Clooney’s co-stars, but the truth isn’t so straightforward.
Whether this credit counts as another collaboration between Pitt and Clooney is questionable at best. It’s more of an in-joke for Ryan Reynolds fans who know about the joke in Deadpool 2. Regardless, IF boasts an all-star cast with or without Pitt. The cast hasn’t translated into too many positive reviews, however, with critics despairing over the complex and meandering plot. IF still has an earnest sweetness to it, and it can connect with anyone in search of their inner child, but it’s not the most original children’s story by any stretch.
8 His Way (2011)
George Clooney & Brad Pitt Give Interviews
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His Way is a documentary based on the life of Jerry Weintraub, a film producer and talent agent with a long legacy in Hollywood. Brad Pitt and George Clooney give interviews as two of the many talents who worked with Weintraub over the years, and the documentary also features Bruce Willis, Julia Roberts, and even George H. W. Bush. It’s apt that Pitt and Clooney both show up in His Way, since Weintraub was pivotal in launching Steven Soderbergh’s Ocean’s Trilogy. Weintraub even appears as an extra in all three Ocean’s movies.
It’s apt that Pitt and Clooney both show up in
His Way,
since Weintraub was pivotal in launching Steven Soderbergh’s
Ocean’s Trilogy.
His Way is an interesting look into the life of a Hollywood icon who most people won’t know about. Even for those who aren’t familiar with Weintraub or his work, His Way provides a peek behind the curtain to show the hectic and constantly changing movie industry. Weintraub wasn’t just a film producer, though. The title of His Way is a reference to Weintraub’s work with Frank Sinatra, and he also rubbed shoulders with Elvis Presley, Led Zeppelin, and many more legendary musicians. His Way is a light and entertaining portrait of a dazzling personality.
7 8 (2012)
George Clooney Plays David Boies & Brad Pitt Plays Judge Vaughn Walker
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8 is a filmed play based on the landmark case that ruled that Proposition 8, which made gay marriage illegal in California, was unconstitutional. Written by Oscar-winning screenwriter Dustin Lance Black, who previously wrote Milk and J. Edgar, 8 uses as much dialogue from the court transcripts as possible. The proceedings were filmed, but they have been locked away, legally barred from seeing the light of day. Instead, 8 tries to recreate the case with as much fidelity as possible, although there are some entirely fictionalized scenes spliced in which take place outside the courtroom.
8
is a filmed play, based on the landmark case which ruled that Proposition 8, which made gay marriage illegal in California, was unconstitutional.
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Brad Pitt plays Judge Vaughn Walker, and George Clooney plays one of the lawyers arguing in favor of gay marriage. The rest of the cast is just as impressive, with Jamie Lee Curtis, Michael Sheen and John C. Reilly. Despite the fact that they are all carrying their scripts around on stage, they still manage to deliver some powerful moments. 8 also has a great sense of humor. By simply reframing some of the absurd statements from the courtroom, the proceedings turn into a comedy. 8 gives audiences permission to laugh at the paradoxical bigotry of the arguments against gay marriage.
6 Wolfs (2004)
George Clooney & Brad Pitt Play Unnamed Fixers
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The problem with
Wolfs
is it just doesn’t materialize into the type of movie these two stars deserve to be making together.
As for feature-length movies starring George Clooney and Brad Pitt, Wolfs is the worst option available. It’s not necessarily that it’s a bad movie; it’s just that, for the first time seeing these two movie stars on screen together in sixteen years, it’s rather underwhelming. For a movie that relies so heavily on the star power of two of the greatest movie stars of their generation, Wolfs should be a lot more enjoyable. It even has a fun crime movie genre premise that feels like it could be a throwback to the types of movies made in the 2000s, but it falls short in almost every regard.
It would be impossible to point a camera at George Clooney and Brad Pitt and not get anything good. The two stars radiate so much charm and talent that even with a worse script, they’d still be fun to watch. And again, Wolfs isn’t bad. There are some hilarious moments that work really well, particularly between the two leads when they’re allowed to banter and poke fun at each other, which is exactly what one would hope for in a comedy starring the two. The problem with Wolfs is it just doesn’t materialize into the type of movie these two stars deserve to be making together.
5 Ocean’s Twelve (2004)
George Clooney Plays Danny Ocean & Brad Pitt Plays Rusty Ryan
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Ocean’s Twelve
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*Availability in US Director Steven Soderbergh Release Date December 10, 2004 Cast George Clooney , Brad Pitt , Matt Damon
After the exhilarating heights of Ocean’s Eleven, Ocean’s Twelve is a predictably difficult sequel. There’s a good reason why heist movies don’t usually have sequels, since the big score feels like such a triumphant finale. After Danny and his team get away with their audacious Las Vegas job at the end of Ocean’s Eleven, there’s no need for a continuation of the story. Ocean’s Twelve was created due to the financial success and the popularity of the first movie, and not because the characters had much more life in them.
After the exhilarating heights of
Ocean’s Eleven, Ocean’s Twelve
is a predictably difficult sequel.
It would have been easy to try and repeat the same formula from the first movie, but Steven Soderbergh takes some admirable swings in Ocean’s Twelve. The story follows the gang across some exotic European locations as they attempt to pull off a couple of seemingly impossible heists while competing with another master thief. Pitt’s character gets a new love interest, played by Catherine Zeta-Jones, but the focus remains on his dynamic with Clooney’s Danny Ocean. Ocean’s Twelve was a low point for the Ocean’s franchise, as none of the heists feel as satisfying or intelligent.
4 Ocean’s Thirteen (2007)
George Clooney Plays Danny Ocean & Brad Pitt Plays Rusty Ryan
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Ocean’s Thirteen
Director Steven Soderbergh Release Date June 8, 2007 Cast George Clooney , Brad Pitt , Matt Damon , Michael Mantell , Elliott Gould , Ray Xifo , Al Pacino , Adam Lazarre-White , Eddie Jemison , Don Cheadle , Shaobo Qin , Casey Affleck , Scott Caan , Bernie Mac , Carl Reiner , Eddie Izzard , Maggie Rowe , Ellen Barkin , Kris Kane , Soledad St. Hilaire , Olga Sosnovska , Jerry Weintraub Expand
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Ocean’s Thirteen marked a return to form for the Ocean’s franchise, even if it didn’t quite recapture the brilliance of Steven Soderbergh’s first movie. The final movie in the trilogy takes things back to basics, with a single heist in Las Vegas. Still, there are a few fun twists to separate it from Ocean’s Eleven. The most obvious of these is the addition of Al Pacino as the new villain. He delivers a characteristically splashy performance, and he seems to have a lot of fun when playing the bad guy.
Ocean’s Thirteen
has enough fun banter and exciting action to make it a crowd-pleasing end to the trilogy.
Pacino’s role doesn’t quite make up for the absence of Julia Roberts, however. Tess goes from being the object of Danny’s desires in the first movie to being a part of the team in the sequel. It would have been interesting to see her taking on even more responsibility in Ocean’s Thirteen, but Soderbergh had other ideas. Ocean’s Thirteen still has enough fun banter and exciting action to make it a crowd-pleasing end to the trilogy. After the modest success of Ocean’s 8, the franchise is being kept alive with an Ocean’s Eleven prequel starring Margot Robbie and Ryan Gosling.
3 Confessions Of A Dangerous Mind (2002)
George Clooney Plays Jim Byrd & Brad Pitt Plays Brad
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Confessions Of A Dangerous Mind
Director George Clooney Release Date December 31, 2002 Cast Sam Rockwell , Drew Barrymore , George Clooney , Julia Roberts , Rutger Hauer
Confessions of a Dangerous Mind is one of George Clooney’s rare directorial efforts. Like most of the other movies he has directed over the years, Clooney gives himself a role in Confessions of a Dangerous Mind, and his directorial debut features Brad Pitt too. Confessions of a Dangerous Mind is based on the autobiography of Chuck Barris, the TV personality who created The Gong Show and The Dating Game, as well as claiming to be an assassin for the CIA. These claims have been denied by the CIA, and they are generally believed to be nothing more than an entertaining fantasy.
Clooney injects a lot of humor into the unbelievable story, with a big helping hand from screenwriter Charlie Kaufman.
Whether Barris’ story is true or not, Confessions of a Dangerous Mind adapts his autobiography as if it’s a factual document. Sam Rockwell delivers a fantastic performance as Barris, swinging between his charming TV persona and his cold-blooded second life as a hitman. Clooney injects a lot of humor into the unbelievable story, with a big helping hand from screenwriter Charlie Kaufman. Confessions of a Dangerous Mind steers clear of the debate over Barris’ honesty. Instead, it plays out his fantasy on the big screen with all the glamour and excitement that he could have hoped for.
2 Burn After Reading (2008)
George Clooney Plays Harry Pfarrer & Brad Pitt Plays Chad Feldheimer
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George Clooney has made several movies with the Coen brothers, including O Brother, Where Art Thou and Hail, Caesar! Brad Pitt joined him for Burn After Reading, a farcical spy story featuring a couple of dimwitted gym employees who stumble onto some files which they believe contain some top-secret government information. Pitt plays a meathead who thinks that he can play the game of espionage, while Clooney is a seasoned professional who represents the glamour-free reality of being a government agent. Burn After Reading’s brilliant cast also includes Frances McDormand, John Malkovich and J. K. Simmons.
The death scene is a great punch line, and a sly meta joke at the expense of anyone excited about seeing Pitt and Clooney’s dynamic.
Burn After Reading isn’t one of the very best Coen brothers movies, but it has a lot of good qualities. Like Fargo and The Big Lebowski, Burn After Reading features a complex criminal plot, with plenty of eccentric characters bouncing off each other. Pitt and Clooney’s characters don’t cross paths until Clooney finds Pitt hiding in a closet, and he immediately, reflexively shoots him in the head. The death scene is a great punch line and a sly meta joke at the expense of anyone excited about seeing Pitt and Clooney’s dynamic.
1 Ocean’s Eleven (2001)
George Clooney Plays Danny Ocean & Brad Pitt Plays Rusty Ryan
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Ocean’s Eleven
Director Steven Soderbergh Release Date December 7, 2001 Cast Brad Pitt , Don Cheadle , Julia Roberts , George Clooney , Matt Damon , Andy Garcia
Ocean’s Eleven is one of the best heist movies of all time, and it inspired plenty of imitators throughout the 2000s and 2010s. George Clooney and Brad Pitt set out to do the impossible – remaking a Rat Pack movie with even more style – and they pulled it off. Clooney and Pitt’s dynamic is never more enjoyable or more aspirational than it is in Ocean’s Eleven. Danny Ocean and Rusty have a friendship that allows them to finish each other’s sentences. Although the other nine members of the gang have their own charms, none of them sparkle quite like the lead duo.
Steven Soderbergh’s slick direction oozes cool, but
Ocean’s Eleven
has enough substance to go with its style.
Steven Soderbergh’s slick direction oozes cool, but Ocean’s Eleven has enough substance to go with its style. The twisty story sets up an elaborate heist with Rube Goldberg-level intricacy. It still presents plenty of surprises in its third act, as twists pile up on top of each other in a beautifully choreographed but breathlessly chaotic finale. Ocean’s Eleven has enough humor and action to keep the pace moving throughout, and it all adds up to a riotously entertaining experience. It’s exciting to see Pitt and Clooney back together for Wolfs, but beating the appeal of Ocean’s Eleven is a tall order.
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