Their virtual onscreen reunion went down at the Dane Cook Presents Feelin' A-Live: Fast Times at Ridgemont High table read, with host Dane Cook bringing together a cast of A-listers to reenact the 1982 classic.
During the event, Aniston and Pitt played Linda Barrett and Brad Hamilton, appearing on screen together for the first time since their 2005 divorce.
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The two actors shared a hilarious moment in the script in which the character of Brad has a sexual fantasy about Linda, resulting in a live reading between the two exes that caused laughs by everyone.
Also featured in the live table read was Cook as Mark "Rat" Ratner, Ray Liotta as Mr. Hand, John Legend as Charles Jefferson, Henry Golding as Mr. Vargas, Shia LaBeouf as Spicoli, Matthew McConaughey as Mike Damone, Julia Roberts as Stacy Hamilton, Sean Penn as a delivery driver, Morgan Freeman reading stage directions and Jimmy Kimmel as all other characters.
Before the table read began, the A-list crew shared a few nervous laughs with Kimmel saying, “Break a leg everybody. Your career is riding on this.”
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His comment raised a few laughs, with someone saying, "This is going to be fantastic."
LaBeouf played the main character, Spicoli — a role previously played by Penn in the film — complete with a cigarette and a shirtless debut as his character.
His performance roused laughs and wide grins from the cast, in particular Penn and Pitt, 56, who has previously worked with LaBeouf in the 2014 film Fury.
At the end of the reading, the actors applauded each other, with Kimmel jokingly asking, "Can we just take it from the top and do it one more time?"
Roberts also congratulated Freeman for his reading, saying, "Morgan Freeman, you’re the MVP!"
Pitt and Aniston, 51, were married from 2000 to 2005, and have rekindled their friendship through the years which culminated in a friendly greeting backstage at the Screen Actors Guild Awards earlier this year.
Cook spoke to PEOPLE before the big night, explaining why he wanted to put such a huge event on as people around the world still struggled with the novel coronavirus pandemic.
"It's hard to not have those really great, dare I say, holy s—, entertainment moments, which we have summer to summer — the big movie or the big moment. And when I didn't see that was happening, when I started seeing the films that I was anticipating most move out of the summertime spot, I thought, man, wouldn't it be great if somehow, someway we could still create a version of that moment? And I think we have the chance to do that, which is so damn cool."
As for how the cast came together, Cook told PEOPLE, "I threw out a bunch of names originally, and was fortunate enough to get a couple of those names pretty quickly. I mean, Jennifer Aniston was lovely and was so gung-ho. Julia Roberts came in within that first week or two, and within 10 days, I knew that this could go the distance. In terms of casting and how we wanted it to come together, there's some expectation of what kind of person should be playing this role or that role, but truly it was about, let's really try to break up the diversity, and let's be unexpected. You know, a live read is a celebration of the written story."