David Letterman’s question that left Jennifer Aniston very uncomfortable
As the interview continued, the conversation shifted to her co-star Vince Vaughn and the nature of their on-screen chemistry. Letterman also brought up rumors about her personal life, including questions about whether her appearance in the film was influenced by Vaughn. Aniston tactfully redirected the questions, suggesting that her co-star would be the better person to ask.
Clips of the interview have resurfaced online, with some fans pointing out how moments like these reflect a different standard of celebrity interviews in the early 2000s—particularly when it comes to how female guests were treated. The conversation has reignited broader discussions around media, tone, and how interviews are shaped by the times.
This wasn’t the only moment that’s being revisited. A 1998 interview between Aniston and Letterman also recently went viral, in which he briefly leaned in and touched her hair—a moment that has drawn mixed reactions today. At the time, it was played off as comedy, and Aniston remained composed, continuing the interview without missing a beat.
Despite these awkward moments, Aniston returned to The Late Show multiple times in the years that followed. One particularly memorable visit came in 2008, when she brought Letterman a gift—a necktie matching the one she famously wore on the cover of GQ. The gesture sparked laughter and warmth between the two, showing once again Aniston’s ability to navigate public moments with charm and professionalism.
While Aniston has never publicly commented on these interviews, the resurfaced clips have fueled online debate about how much late-night culture has changed—and how society is reevaluating the norms of celebrity interviews from decades past.
As standards continue to evolve, moments like these offer a chance for reflection—not only on how interviews are conducted, but on how public conversations around media, tone, and respect have grown more thoughtful over time.