David Letterman, once praised as the king of late-night TV, is now being scrutinized for past interviews that made guests uncomfortable—especially women. One moment gaining renewed attention is Jennifer Aniston’s 2006 Late Show appearance, which left viewers uneasy.

While promoting The Break-Up, Aniston wore a black blouse and shorts. Instead of focusing on her movie, Letterman commented, “That’s a tremendous outfit… because you have tremendous legs.” When Aniston tried to move on, he continued, saying, “I can’t get over your legs,” and joked that someone should record “the shot.”

The exchange grew more awkward when Letterman questioned her rumored romance with Vince Vaughn, even asking if he wanted her “to appear naked in the film.” Aniston laughed it off, replying that he should ask Vaughn himself.

This wasn’t their first uncomfortable encounter—back in 1998, Letterman had shocked viewers by grabbing her neck and sucking on a strand of her hair.

Clips of these interviews have resurfaced, prompting outrage and reflection on how women were once treated in late-night television. Though Aniston remained professional, these moments now highlight how much attitudes toward respect and boundaries have changed.