Jennifer Aniston Once Felt Doing a Film With Her Ex-Husband Brad Pitt Was Asking for Trouble

Jennifer Aniston and her ex-husband Brad Pitt were both huge names in the film industry in their own right. But while they were a couple, the two stars decided it was best to avoid starring in films together.

Have Brad Pitt and Jennifer Aniston ever done any projects together?

Brad Pitt and Jennifer Aniston smiling at a movie premiere.
Jennifer Aniston and Brad Pitt | Jon Kopaloff/FilmMagic

Although Pitt and Aniston were both actors, they co-starred in very few film projects together. The only exception during their relationship was a guest appearance Pitt had in Aniston’s hit show Friends.


Apart from the hit sitcom, the two somewhat reunited for a virtual table read of Sean Penn’s Fast Times At Ridgement High for a fundraiser.

The event caught the attention of many fans since it saw Aniston and Pitt working alongside each other years after their divorce. But Aniston shared she and Pitt have always kept in touch as friends, which made their reunion not as odd as some may have thought.

“You know, Brad and I are buddies. Like, we’re friends and we speak. And there’s no oddness at all, except for everyone that probably watched it and was wanting there to be or assumed it to be,” she once said in an interview on The Howard Stern Show (via Cinemablend).

Jennifer Aniston once felt working alongside Brad Pitt would’ve been a mistake

At the height of their relationship, both Aniston and Pitt had their hands tied with several film projects. But given the couples’ A-list status, many wondered about the possibility of Aniston and Pitt combining their star power for a movie. Aniston didn’t outright dismiss the idea, but she figured a Pitt and Aniston film wouldn’t happen anytime soon.

“That would be just asking for trouble. You wouldn’t even see the movie, because it would be too much of a show in another way. Maybe years down the line, if the right thing came along, of course, we’d love to. Ocean’s Twenty, maybe,” she once told BBC about the idea.

Pitt shared a similar sentiment. The Troy star pointed out that films starring real-life Hollywood couples weren’t doing too well. And Pitt wasn’t too confident that he and Aniston would be the ones to break the pattern.

“You look at past case studies of couples working together in films, and the odds are really against us,” Pitt once said in an interview with News 19.

Jake Gyllenhaal once felt awkward meeting Brad Pitt after having racy scenes with Jennifer Aniston in ‘The Good Girl’

They may have never decided to be in front of the camera on the big screen. But Pitt and Aniston would apparently support each other while they worked on other films. Aniston once offered Pitt a little help with his Fight Club role. Pitt would also stop by to visit his then-wife on film sets like The Good Girl.

Aniston was working alongside Jake Gyllenhaal at the time. In an interview with W magazine, Gyllenhaal described the awkward encounter he had with Aniston’s ex when he stopped by.

“I was working with Jennifer Aniston, who was his wife at the time, and there were a lot of very racy scenes. I remember putting my hand out to shake his, and accidentally hitting the door. He said, so confidently and kindly, ‘Well, you have another one. It’s all right.’ He was very, very, very sweet to me, and it was actually a really lovely exchange. But, yeah—I was starstruck,” Gyllenhaal remembered.

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