David Letterman, celebrated for his quick wit and decades as a late-night host, has had moments in his career that are now viewed through a very different lens. One of the most talked-about examples is his 2006 interview with Jennifer Aniston while she was promoting The Break-Up. During their conversation, Letterman repeatedly commented on Aniston’s legs, saying things like, “You have tremendous legs. Fantastic legs. You can only wear that if you have well-shaped, muscular legs.” Though intended as humor at the time, the remarks left Aniston visibly uncomfortable. She responded with grace, laughing politely and explaining that she had chosen her outfit simply because of the warm weather.
The exchange became even more awkward when Letterman pressed her about her rumored relationship with co-star Vince Vaughn and scenes from the film. Staying composed, Aniston skillfully deflected, suggesting he direct those questions to Vaughn instead. Still, Letterman continued to comment on her appearance throughout the interview — behavior that, by today’s standards, many now view as crossing professional boundaries.
This wasn’t the first time Aniston experienced discomfort on his show. In a 1998 appearance, Letterman unexpectedly touched her hair during their interview, an act that left both the audience and Aniston momentarily stunned. At the time, it was brushed off as comedic television, but in hindsight, it’s widely regarded as inappropriate.
Reflecting on these interviews, cultural critics and viewers alike note how much attitudes toward celebrity treatment and on-air “humor” have evolved. While Letterman remains a legendary figure in television, these moments serve as reminders of how media norms have shifted — and how Jennifer Aniston’s professionalism and composure continue to earn admiration long after the awkward laughter faded.