Aniston, promoting her film The Break-Up, appeared stylish in a black blouse and shorts. But instead of focusing on her movie, Letterman repeatedly commented on her legs, saying, “That’s a tremendous outfit… because you have tremendous legs.” Aniston, clearly caught off guard, laughed politely and moved on, but the host continued to bring up her appearance.

He later remarked, “I can’t get over your legs,” and even joked that someone should record the show because of “the shot.” The repeated focus on her body made the interview increasingly awkward, with Aniston visibly trying to remain composed.

Letterman then pressed her about her rumored romance with co-star Vince Vaughn, even asking whether he wanted her to appear naked in the film. Aniston hesitated before deflecting, saying he should have asked Vaughn that question.

This wasn’t the first time Letterman had made her uncomfortable. In a 1998 interview, he unexpectedly grabbed her neck and sucked on a strand of her hair, a moment that has since gone viral for its invasiveness.

Clips of these encounters have resurfaced online, sparking outrage and renewed discussion about how women were treated in late-night television.

Despite these moments, Aniston continued to appear on the show, handling each situation with professionalism and grace.

Today, these interviews serve as reminders of how much cultural standards have shifted — and how behavior once dismissed as “humor” is now rightly seen as inappropriate and disrespectful.