David Letterman, once a late-night icon known for his sharp humor, is now facing renewed scrutiny over past interviews—especially those with female guests. A 2006 interview with Jennifer Aniston, promoting The Break-Up, has resurfaced, drawing criticism for its uncomfortable tone. Instead of focusing on her film, Letterman repeatedly commented on Aniston’s appearance, particularly her legs, making her visibly uncomfortable. His remarks, once brushed off as humor, are now being reconsidered as inappropriate.

The interview didn’t just stop at compliments. Letterman also asked invasive questions about Aniston’s relationship with Vince Vaughn and whether it was Vaughn’s idea for her to appear nude in the film. As Aniston tried to maintain professionalism, Letterman returned to the topic of her legs several more times. One particularly cringeworthy comment about “TiVoing the shot” she was in left Aniston clearly uneasy, a reaction that resonates strongly in today’s more sensitive cultural climate.
This wasn’t the only awkward encounter between the two. In a 1998 interview, Letterman shocked viewers by unexpectedly putting Aniston’s hair in his mouth. She pulled away and used a tissue to wipe off the saliva—an unsettling moment that has gone viral multiple times since. While Aniston has never publicly addressed these incidents, many viewers now see them as examples of how women in media were often subjected to uncomfortable situations, masked as comedy.
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Despite these awkward moments, Aniston continued to appear on The Late Show, always handling herself with grace. Yet, as clips resurface, they’re fueling broader discussions about sexism and boundaries in the entertainment industry. What was once dismissed as typical late-night banter is now prompting reflection on how female celebrities were treated—and how much has changed, or still needs to.