David Letterman’s question that left Jennifer Aniston very uncomfortable

David Letterman was once celebrated as the king of late-night television, admired for his sharp wit, quirky humor, and unconventional interview style. However, as audiences have begun to reassess older media through a modern lens, many of his past interviews have drawn renewed scrutiny, particularly those involving female guests. One of the most widely discussed examples is Jennifer Aniston’s 2006 appearance on The Late Show, which left many viewers uncomfortable both then and now.

Aniston was promoting her romantic comedy The Break-Up and arrived in a chic black blouse and shorts, exuding her usual charm and warmth. Instead of focusing on her film, however, Letterman immediately commented on her physical appearance, saying, “That’s a tremendous outfit… because you have tremendous legs.” His remark set a tone that felt inappropriate and dismissive of her work. Though Aniston responded with polite laughter, it was clear that the compliment caught her off guard. As the conversation went on, Letterman returned to the topic multiple times, repeating that he “couldn’t get over” her legs and even suggesting that the moment should be recorded for “the shot.”

What might once have been brushed off as playful banter now reads as uncomfortable, even invasive. Throughout the exchange, Aniston tried to steer the conversation back to her movie, maintaining her composure while enduring a situation that grew increasingly awkward. Viewers watching the clip today often note her professionalism and restraint, qualities that highlight how often women in entertainment were expected to handle inappropriate behavior gracefully.

The interview grew more uncomfortable when Letterman shifted to her rumored romance with co-star Vince Vaughn. He asked whether Vaughn had wanted her to appear naked in the film, a question that left Aniston momentarily speechless before she tactfully replied that he should have asked Vaughn that question instead. Her attempt to deflect the comment with humor reflected both her quick thinking and her need to manage an interview that had veered far from promoting her work.

This was not the first time Letterman had made her visibly uncomfortable. In a 1998 interview, he surprised Aniston by reaching toward her neck and placing a strand of her hair in his mouth, an act that has since resurfaced online to widespread criticism. The moment, once treated as an odd bit of late-night spontaneity, is now viewed as deeply invasive and inappropriate. Many who have revisited the footage express disbelief that it was ever aired without objection.

Clips of both encounters have circulated across social media, sparking outrage and prompting discussions about how women were often treated on talk shows during the late 1990s and early 2000s. What was once accepted as part of the entertainment landscape is now recognized as an example of the casual sexism that pervaded much of the media at the time.

Despite these uncomfortable experiences, Jennifer Aniston continued to appear on The Late Show and handled each interview with remarkable poise. Her professionalism in the face of discomfort only underscores how frequently women in public life were forced to navigate inappropriate comments while maintaining their image and career.

Today, these interviews serve as powerful reminders of how far cultural standards have evolved. Behavior that was once excused or laughed off is now widely understood as disrespectful. The reevaluation of such moments not only highlights progress in how women are treated in media but also encourages continued reflection on the importance of respect and accountability in entertainment.