The Question That Left Jennifer Aniston Uncomfortable How a David Letterman Interview Sparked New Conversations

David Letterman’s legacy as a late-night icon is undeniable, but many of his past interviews look very different when viewed through today’s cultural lens. One moment that continues to resurface involves Jennifer Aniston’s 2006 appearance on The Late Show, where what should have been a lighthearted promotional chat quickly shifted into uncomfortable territory. Aniston, there to discuss her film The Break-Up, was suddenly faced with Letterman’s fixation on her appearance rather than her work, setting the tone for an interview that has not aged well. Dressed in chic black shorts and a stylish blouse, she appeared poised, yet visibly unsettled when Letterman began complimenting—and then repeatedly commenting on—her legs.

What made the moment increasingly uneasy was Letterman’s persistence. Each time Aniston attempted to steer the conversation back toward her film, he circled back to her legs, praising them with remarks that felt intrusive even at the time. The discomfort deepened when he pressed her about rumors surrounding her relationship with Vince Vaughn and questioned whether Vaughn had encouraged her to appear nude in the movie. Caught off guard, Aniston deflected gracefully, but the imbalance of the exchange was unmistakable. His repeated comments, paired with a remark about hoping someone at home was recording the “shot,” left viewers—then and now—cringing at how much the focus had shifted away from her professionalism.

This wasn’t the first time Aniston had endured such an uncomfortable dynamic with Letterman. A 1998 interview between the two remains one of his most criticized moments: he unexpectedly grabbed her from behind and put a strand of her hair in his mouth. The shock on Aniston’s face was immediate, and though she attempted to smile her way through it, the clip has resurfaced over the years as a troubling example of behavior once passed off as “late-night humor.” As modern audiences revisit the footage, many express disbelief at how normalized such invasiveness once was, and how gracefully Aniston was expected to—and did—handle it.

Despite these unsettling interactions, Aniston continued to appear on The Late Show, meeting each visit with the same warmth and professionalism she’s known for. Her later appearances, including a playful 2008 segment where she gifted Letterman a necktie matching her famous GQ cover, carried a lighter tone but still underscored a recurring pattern in the host’s approach to female guests. Today, as these clips circulate widely online, they’re prompting deeper conversations about how women in Hollywood have long been treated in interviews. What was once brushed aside as comedy is now recognized as part of a broader issue—one that audiences are increasingly unwilling to ignore.