‘Ocean’s Eleven’ Cast Then & Now: See George Clooney, Julia Roberts & More 19 Years Later

In the mood for a heist? Well, ‘Ocean’s Eleven’ is celebrating its 19th anniversary. This star-studded cast features basically all of Hollywood’s biggest and best actors. Take a look at the cast then and now.

Ocean’s Eleven became a massive hit when it was released on Dec. 7, 2001. Everyone was intrigued by Danny Ocean and Rusty Ryan’s plan to steal $160 million from casino owner Terry Benedict. The movie, directed by Steven Soderbergh, became such a sensation that it spawned two sequels.

The film stars some of Hollywood’s biggest A-listers. Even after all these years, it’s such a fun ride to George Clooney, Brad Pitt, and more onscreen together. See what the cast has been up to since 2001.

George Clooney

George Clooney, 59, starred as Danny Ocean in Ocean’s Eleven and the additional two sequels. Just 5 years later, George won his first Oscar for Best Performance by an Actor in a Supporting Role for his performance in Syriana. He’s also earned acting Oscar nods for his roles in Michael Clayton, Up in the Air, and The Descendants. In 2013, he won the Academy Award for Best Picture for producing the movie Argo.

The actor has continued to step behind the camera. He’s directed films like Good Night, and Good Luck, The Ides of March, and The Midnight Sky, which will be released Dec. 23 on Netflix.

He married human rights lawyer Amal Alamuddin in 2014. Amal gave birth to twins Ella and Alexander in 2017.

Julia Roberts

Julia Roberts, 53, played Tess Ocean in both Ocean’s Eleven and Ocean’s Twelve. The same year as Ocean’s Eleven, Julia won the Best Actress Oscar for Erin Brockovich. She reunited with George for his directorial debut film, Confessions of a Dangerous Mind.

Since 2001, the actress has starred in other films like Valentine’s Day, August: Osage County, Wonder, and Ben is Back. She earned another Oscar nomination for August: Osage County. The actress also notably starred in the HBO film The Normal Heart and starred in the Amazon Prime Video series Homecoming.

Julia married Danny Moder in 2002. Julia gave birth to twins in Nov. 2004 and had a son in 2007.

Brad Pitt

Brad Pitt, 56, starred as Robert “Rusty” Ryan in the Ocean’s trilogy. In the years following Ocean’s Eleven, Brad became one of Hollywood’s biggest stars with movies like Mr. & Mrs. Smith, Troy, and World War Z. He’s also become a prolific producer. Brad won his first Oscar for Best Supporting Actor in 2020 for his role in Once Upon A Time in Hollywood. His upcoming films include Babylon and Bullet Train.

At the time Ocean’s Eleven was released, Brad was married to Jennifer Aniston, 51. They divorced in 2005. Brad and Angelina Jolie, 45, fell in love after meeting on the set of Mr. & Mrs. Smith. They married in 2014 and have 6 kids: Maddox, Pax, Zahara, Shiloh, Vivienne, and Knox. Angelina filed for divorce in 2016. Brad and Angelina are still in court over their divorce and custody of their kids 4 years later.

Don Cheadle

Don Cheadle, 56, played Basher Tarr. He also reprised his role in the subsequent sequels. He earned his first Oscar nomination in 2005 for his performance in Hotel Rwanda. Don notably replace Terrence Howard in the role of James Rhodes/War Machine in Iron Man 2. He has continued to play the role in multiple Marvel movies.

From 2012 to 2016, he starred in the TV series House of Lies. He won the Golden Globe for Best Performance by an Actor in a Television Series – Comedy or Musical in 2013. Since 2019, he has starred in the Showtime series Black Monday, which has earned him back-to-back Emmy nominations.

Matt Damon

Matt Damon, 50, starred as Linus Caldwell in all 3 Ocean’s movies. Matt was already an Oscar winner when he starred in Ocean’s Eleven, and his career has only gotten bigger since then. In 2002, Matt kicked off the Bourne franchise, and he’s starred in 4 out of the 5 movies. Matt’s other notable roles include The Departed, The Martian, Ford v Ferrari, and more. He’s been nominated for an additional 3 Oscars since Good Will Hunting.

Matt married Luciana Bozán Barroso in 2004 after meeting at a bar where she was bartending. They have 4 children together, including a stepdaughter from Luciana’s previous marriage.

Andy Garcia

Andy Garcia, 64, starred as Terry Benedict in the Ocean’s movies. In between Ocean’s movies, Andy co-wrote, directed, and starred in The Lost City. His other notable movies include Mamma Mia! Here We Go Again, Book Club, and The Mule. He recently starred in the films Words on Bathroom Walls and Ana.

Bernie Mac

Bernie Mac played Frank Catton in all three Ocean’s movies. Ocean’s Thirteen was one of his final film roles. He also starred in movies like Charlie’s Angels: Full Throttle, Guess Who, and Bad Santa. Bernie notably starred in The Bernie Mac Show from 2001 to 2006. Bernie sadly died at the age of 50 in 2008 due to complications from pneumonia.