David Letterman’s Interview with Jennifer Aniston Resurfaces: Fans Revisit an Uncomfortable Moment
David Letterman, once celebrated for his sharp wit on late-night TV, is now under renewed scrutiny for past interviews that haven’t aged well—especially one involving Jennifer Aniston.
During a 2006 appearance on The Late Show, Aniston was promoting The Break-Up when the conversation took an awkward turn.
Dressed in black shorts and a blouse, the actress quickly became the focus of Letterman’s attention—not for her film, but for her legs.
He repeatedly complimented them, even saying, “You can only wear that if you have lovely, well-shaped, muscular, lengthy legs.”
Despite her efforts to deflect with humor, Aniston’s discomfort was visible. The interview only grew more uneasy as Letterman returned to the topic multiple times and later asked about nude scenes and her rumored relationship with co-star Vince Vaughn.
This wasn’t the first time Aniston faced awkward moments on The Late Show. In a 1998 interview, Letterman shocked viewers by grabbing her neck and sucking on her hair—leaving her visibly uncomfortable.
To her credit, Aniston always handled these moments with grace. She even returned to the show in 2008, this time offering a thoughtful gift—a tie she wore on the cover of GQ.
While the interaction was lighter, past interviews now serve as reminders of how much standards for respectful media conduct have evolved.
Clips from these interviews are trending once again, sparking conversation about celebrity treatment in the media—and how some moments are better left in the past.
