David Letterman was once a late-night TV icon, but some of his old interviews haven’t aged well.
In 2006, Jennifer Aniston appeared on The Late Show to promote The Break-Up. Instead of focusing on the movie, Letterman repeatedly complimented her legs, even saying, “I can’t stop looking at your legs.”
He also pressed her about Vince Vaughn and her nude scene in the film, making the interview increasingly awkward.
It wasn’t their first uncomfortable moment. In 1998, Letterman famously grabbed Aniston’s neck and sucked on a strand of her hair.
Aniston later returned to the show, but resurfaced clips of these interviews continue to spark debate over how differently late-night humor is viewed today.
