It has been 20 years since Jennifer Aniston finalized her divorce from Brad Pitt, but the high-profile split remains one of the most talked-about events in Hollywood history. In her new Vanity Fair cover story, Aniston reflected on the relationship’s ending, almost exactly two decades after her original September 2005 Vanity Fair cover, which was her first in-depth interview following the breakup.
“I haven’t looked at that article in forever,” Aniston said in her new interview, referencing the 2005 feature. “I just remember the experience of doing it—which was kind of jarring. It was also such a vulnerable time. But yeah, that was one for the memoirs.”
Aniston and Pitt married in July 2000, but in January 2005, they announced their separation. By April of that year, Pitt had gone public with his relationship with actress Angelina Jolie. The divorce was finalized in October 2005, only weeks after Aniston’s widely discussed Vanity Fair interview hit newsstands. Less than a year later, in May 2006, Pitt and Jolie welcomed their first biological child, Shiloh Jolie-Pitt, now known as Shiloh Nouvel Jolie.
Elsewhere in the interview, Aniston reflected on the unusual overlap between her personal and professional life during that period. She was filming the romantic comedy The Break-Up with Vince Vaughn at the same time she was experiencing her real-life split from Pitt.
“I might’ve just gone through a separation—that little separation, I’m sure nobody remembers that,” she joked, referencing the intense media coverage of her marriage’s end. “It was kind of cathartic to go right from that. So when they came to me with the role, they were a little nervous about making the offer, thinking, ‘Oh, is that insensitive? Is it inappropriate?’ But I actually thought, ‘What a great opportunity.’”
The new Vanity Fair profile highlights how Aniston’s career and personal life have often intertwined in the public eye, with the actress candidly acknowledging the lasting public fascination with one of Hollywood’s most famous breakups.
