David Letterman, once celebrated for his sharp late-night humor, is now facing renewed scrutiny over past interviews with female guests. A resurfaced moment from Jennifer Aniston’s 2006 appearance on The Late Show has drawn particular attention.

Aniston was there to promote The Break-Up, but Letterman focused less on her film and more on her appearance. He repeatedly commented on her legs, telling her, “That’s a tremendous outfit… because you have tremendous legs.” Although she laughed politely and tried to move forward, he continued to return to her body, later saying, “I can’t get over your legs,” and even joking that someone should record the episode because of “the shot.” The exchange grew increasingly uncomfortable as Aniston tried to stay composed.

He also pushed her about her rumored relationship with co-star Vince Vaughn and asked whether Vaughn wanted her to appear naked in the movie. Aniston sidestepped the question by suggesting he should ask Vaughn instead.

This wasn’t the first uncomfortable moment between them. In a widely shared 1998 clip, Letterman unexpectedly grabbed her neck and sucked on a piece of her hair—an action now viewed as invasive and inappropriate.

The resurfaced videos have sparked criticism and new conversations about how women were treated in late-night television. Despite these awkward encounters, Aniston continued appearing on the show, managing each situation with professionalism.

Today, these clips highlight how cultural expectations have changed and how behavior once excused as humor is now seen very differently.