Certain stars just tend to be drawn working together. Ben Affleck and Matt Damon, Emma Stone and Ryan Gosling, and Adam Sandler and Drew Barrymore just to name a few. Yet one high-profile duo that has really enjoyed working together and audiences enjoy watching in films areGeorge ClooneyandJulia Roberts.

These are two of the biggest stars in movies, whose names could instantly draw in a crowd. They both are Academy Award winners and still maintain a certain level of star power, despite it having faded away in an age where franchises and pre-existing characters are the draws for audiences. While they both had long and accomplished careers before they started collaborating at the beginning of the 21st century, these two have worked together on five films. Here they are, ranked.

Money Monster with George Clooney and Julia Roberts

5Money Monster

Money Monsterwas a 2016 crime thriller that was directed by Jodi Foster and featured George Clooney and Julia Roberts in the lead role. Clooney played a financial television host while Roberts starred as his producer who are put in a hostage situation when an investor takes the building under control.Money Monsterreceived mixed reviews from critics despite the talent in front and behind the camera. The movie was a success though grossing $93 million at the worldwide box office though it is likely the collaboration between the two stars most people forget.

4Ticket to Paradise

Clooney and Roberts' most recent collaboration was the 2022 romantic comedyTicket to Paradise, where the two play a divorced couple who decide to team up to stop their daughter from marrying a man she just met while on her summer after graduating from college. Over the course of the film the two need to not only accept their daughter’s decision but also begin to rekindle their feelings for one another.

Related:Best Julia Roberts Movies, Ranked

Ticket to Paradisemight not be the most groundbreaking film for either actor and is certainly their lightest collaboration in terms of tone. Yet the two not only have great chemistry but embrace their status as older more mature stars and work very well in comedy.Ticket to Paradisewas a nice returnto adult-skewing romantic comedies at the box office and was a hit at the box office grossing $168 million worldwide.

3Confessions of a Dangerous Mind

Confessions of a Dangerous Mindis an interesting collaboration between George Clooney and Julia Roberts, as the two not only co-star in the film together, but this film marks George Clooney’s first film as a director (though he was certainly not the right fit to direct a Charlie Kaufman screenplay). The movie tells the story of real-life game show host Chuck Barris who claimed he was also an operative for the CIA, one which the CIA denies.

Clooney filmed the movie right afterOcean’s Eleven, andit shows he enjoyed working with Roberts so well that he cast her as one of the leads for his film.Confessions of a Dangerous Mindwas a critical hit and not onlysolidified Clooney as a directorbut also helped establish the long-running working relationship between Clooney and Roberts.

Ticket to Paradise with George Clooney and Julia Roberts

2Ocean’s Twelve

The follow-up toOcean’s Eleven,Ocean’s Twelve, in the tradition of many sequels likeThe Great Muppet CaperandNational Lampoon European Vacation,takes the franchise out of the United States and into a global setting. In a nice contrast to the first film, where Roberts' character Tess was essentially Danny’s ultimate end goal and prize, here she gets to be part of the team, being the 12th member.

Related:The Best George Clooney Movies, Ranked

The film uses the funny real-world casting of Julia Roberts to have Tess in the movie pose as Julia Roberts to steal something, only to be accidentally sabotaged by Bruce Willisplaying himself in the movie, and thinking he is talking to the real Julia Roberts. It is a fun bit of meta humor about the casting and a fine line that only a filmmaker like Steven Soderbergh and a star like Roberts can pull off. It is a real shame that Roberts did not return forOcean’s Thirteen.

1Ocean’s Eleven

The first collaboration between George Clooney and Julia Roberts is still their best.Ocean’s Elevenwas a remake of the classic Rat Pack film of the same name from the 1960s, updating A-list stars from that filmlike Frank Sinatrato the biggest stars in Hollywood at the turn of the millennium. Clooney plays Danny Ocean, a thief who decides to rob three of the biggest casinos in Las Vegas with a crew of thieves. It is later revealed the three casinos he has chosen are all owned by the man who is dating his ex-wife Tess, played by Julia Roberts, and Danny’s real goal is to get his wife back.

Clooney and Roberts don’t share a scene together till halfway through the movie but when they do, they light up the movie, having great chemistry that feels lived in and tinged with a hint of sadness while also a spark of romance. A famous story from the production goes that Clooney sent Roberts a card asking her to be in the movie with a $20 bill in it, joking about the idea that Roberts reportedly got $20 million a picture. Roberts agreed to be in the movie and the rest is history as the two have now solidified a great working relationship that has delighted audiences for over twenty years.

George Clooney and Sam Rockwell in Confessions of a Dangerous Mind (2002)

Ocean’s Twelve

George Clooney and Brad Pitt in Ocean’s Eleven