David Letterman, known for his sharp wit and long career as a late-night host, has had interviews that, in today’s context, are viewed differently. One example is his 2006 interview with Jennifer Aniston while she promoted the film The Break-Up. During the 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.” While meant as humor at the time, it left Aniston visibly uncomfortable. She handled the situation professionally, laughing it off and explaining she had chosen her outfit because of the warm weather. The interview became more awkward when Letterman asked about her rumored relationship with co-star Vince Vaughn, and even about scenes in the film.
Aniston deftly redirected, suggesting he ask Vaughn instead. Throughout the interview, Letterman continued to comment on her appearance, creating a pattern that many viewers now see as inappropriate. This was not the first time Letterman made Aniston uncomfortable. In a 1998 interview, he handled her hair in a way that many today would consider invasive. Despite these moments, Aniston maintained her composure, demonstrating professionalism and grace.
Looking back, these interviews highlight how perspectives on celebrity interactions and humor have changed. While Letterman was a beloved host, moments like these serve as a reminder that what was once considered playful or funny can be experienced as uncomfortable and even disrespectful. Jennifer Aniston’s poise throughout these situations has remained widely respected.
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