David Letterman was once considered the king of late-night television, but some of his past interviews are now being viewed through a different lens. One exchange with Jennifer Aniston during her 2006 appearance on The Late Show has resurfaced online, leaving many viewers uncomfortable.

While Aniston was promoting The Break-Up, Letterman quickly shifted the conversation away from her film and toward her appearance. He praised her outfit, saying, “That’s a tremendous outfit… because you have tremendous legs,” before returning to the topic several times. Aniston smiled politely and tried to continue the interview, but the repeated remarks drew attention away from her work.

The awkwardness continued when Letterman added, “I can’t get over your legs,” and joked that someone should record the show because of “the shot.” He also questioned her about rumored boyfriend Vince Vaughn and even asked whether Vaughn wanted her to appear naked in the movie. Aniston briefly paused before cleverly avoiding the question, suggesting he should ask Vaughn instead.

The 2006 interview also reminded viewers of an earlier appearance in 1998, when Letterman unexpectedly grabbed Aniston’s neck and sucked on a strand of her hair. The clip has since gone viral, with many people describing the moment as invasive and inappropriate.

As these interviews continue circulating online, they have sparked renewed conversations about how female celebrities were treated on late-night television. Although Jennifer Aniston handled the uncomfortable moments with professionalism and grace, many viewers now see the behavior once dismissed as comedy as a clear example of disrespect, reflecting how public attitudes and cultural standards have changed over time.