David Letterman, once a late-night icon, is now facing criticism for past interviews with female guests, especially Jennifer Aniston. A 2006 Late Show appearance has resurfaced, where Letterman repeatedly focused on Aniston’s legs instead of her film The Break-Up, making her visibly uncomfortable.

Wearing a black blouse and shorts, Aniston tried to redirect the conversation, but Letterman persisted with comments like “tremendous” and “well-shaped” legs. He also pressed her about a rumored romance with Vince Vaughn and nudity in the film, despite her attempts to stay composed.

This wasn’t their first awkward moment—back in 1998, Letterman bizarrely sucked on a strand of her hair on air. That clip, along with others, has gone viral, prompting renewed scrutiny.

Aniston continued appearing on the show, including a 2008 visit with a playful gift, but even that exchange included innuendo. Rewatching these interviews today underscores how cultural norms have shifted, sparking reflection on boundaries and respect for women in media.