David Letterman, once celebrated for his late-night wit, hasn’t aged well in critics’ eyes—especially his interviews with Jennifer Aniston. A 2006 appearance on The Late Show promoting The Break-Up became infamous for Letterman repeatedly fixating on Aniston’s legs. Wearing black shorts and a blouse, Aniston was praised over and over, leaving her visibly uncomfortable despite handling it with grace.
Letterman also pressed her on personal topics, including rumors about co-star Vince Vaughn and a nude scene in the film. This wasn’t Aniston’s first awkward encounter with him; a 1998 interview included him grabbing her neck and sucking a strand of her hair.
Despite these moments, Aniston returned to the show in 2008 wearing a pink dress to promote Marley & Me, this time showcasing both her charm and thoughtfulness. She gifted Letterman a Brooks Brothers tie from her GQ cover shoot, leading to playful banter and a lighthearted moment—proving she could rise above even the most awkward encounters.