Throughout the late 90s to 2005, Jennifer Aniston and Brad Pitt were Hollywood’s favorite couple. Although the duo starred in an episode of the NBC sitcom FRIENDS, once, there was a time when both the stars were considered for the same Martin Scorsese film. Unfortunately, the dream of working together did not come true for the former lovebirds.
Scorsese’s The Departed ultimately became a classic with a star-studded cast of Leonardo DiCaprio, Matt Damon, and even Jack Nicholson. However, before all the actors were cast, both Aniston and Pitt were initially set to be a part of the now iconic film.
When Jennifer Aniston and Brad Pitt almost starred in a film together
In the landscape of Hollywood, casting choices often define the success or failure of a film. Yet, sometimes, the most surprising combinations can lead to unexpected outcomes. One such case involves the legendary director Martin Scorsese and his iconic 2006 thriller, The Departed.
According to reports from Far Out Magazine, Brad Pitt was initially set to take on Matt Damon’s role of Colin Sullivan. However, the actor chose to turn down a chance to star in the film. Instead, he decided to co-produce it. In an interview with Interview Magazine, the 60-year-old revealed how things played out.
I developed that for two and a half years. We fought for that movie, and then we got William Monahan on the script.
Although Pitt would have loved to be a part of Scorsese’s 2006 film, his heart lay in the production of it all. As for Jennifer Aniston, a post on X revealed that the actress had once been considered for the role of Dr. Madolyn Madden. However, the role eventually went to Vera Farmiga.
While Pitt and Aniston never had the chance to share the big screen together, they made do with their brief yet hilarious interaction on the beloved NBC sitcom in 2001.
Jennifer Aniston and Brad Pitt on FRIENDS
Long before their high-profile divorce, Jennifer Aniston and Brad Pitt starred in an episode of the NBC sitcom FRIENDS. Although the actress was a beloved cast member, her husband at the time wound up playing a character she knew from high school.
However, their relationship was far from normal. In fact, in the episode titled, The One with the Rumor, Aniston played Pitt’s high school bully who had fat-shamed him. Although the actor’s character, Will, seemed to be in the best shape of his life, he hadn’t managed to let go of the past.
After making his way to a Thanksgiving dinner with the gang, Pitt let it slip that he and David Schwimmer’s Ross had been a part of the “I hate Rachel Green club.” While that did not seem too bad, the now 60-year-old also wound up admitting to starting rumors about the former cheerleader.
The scene where Will exposes Rachel’s high school reputation, coupled with Aniston’s comedic reactions, created a memorable moment that resonated with audiences. In fact, it even showcased the lighthearted yet sharp humor that the beloved show was known for.
Years after Aniston and Pitt co-starred on the show, the 55-year-old sang nothing but praises about her ex-husband’s brief yet hilarious appearance on the iconic show.
Stream Jennifer Aniston’s FRIENDS on Netflix.
