David Letterman has long been recognized as a pioneer of late-night television, celebrated for his quick wit and influence on the genre. But as many iconic moments from his show resurface online, some interviews are being viewed in a new light—and not all are standing the test of time.
One such moment involves actress Jennifer Aniston, who appeared on The Late Show with David Letterman in 2006 to promote her film The Break-Up. At the time, the interview seemed like another celebrity chat. But in recent years, clips have been shared widely on social media, prompting viewers to reflect on the tone and focus of the conversation.
An Interview That Left Viewers Divided
During the interview, Aniston wore a stylish black outfit consisting of a blouse and shorts—perfectly appropriate for the summer heat. Letterman complimented her appearance, with comments focused on her legs. While many late-night interviews include light banter, some viewers have noted that the repeated focus on her appearance made the moment feel more awkward than playful.
Aniston, ever professional, responded with her signature humor and grace. She brushed off the remarks, attributing her choice of attire to the warm weather. However, the host returned to the subject more than once, which some viewers now say overshadowed the reason she was there—to talk about her work.
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.
An Earlier Interview Under Scrutiny
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.
Looking Back—and Looking Forward
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.