David Letterman was once praised for his humor and interview style, but not all of his past moments have aged well. One particular interview with Jennifer Aniston stands out as an example.
In 2006, Aniston appeared on The Late Show with David Letterman to promote The Break-Up, a film she starred in alongside Vince Vaughn. At first, it seemed like a typical late-night talk show conversation. But looking back, some moments now feel uncomfortable.
Early in the interview, Letterman focused on Aniston’s outfit, particularly her legs. He repeatedly complimented them, and the camera followed his remarks with close-up shots. While Aniston laughed off the comments, she appeared uneasy.
Despite her efforts to shift the conversation, Letterman continued bringing up the topic. At one point, he even asked if Vince Vaughn had suggested that she appear without clothes in the movie. Aniston briefly paused before redirecting the question, suggesting Letterman should have asked Vaughn himself.
Letterman’s remarks about Aniston’s legs weren’t limited to that interview. He brought them up again while discussing her co-star, saying, “I can’t get over your legs.” At another point, he even joked about hoping someone recorded the episode so they could rewatch the shot he was referring to. Aniston’s expression made it clear she felt awkward.
This wasn’t the only time Letterman’s interactions with Aniston raised eyebrows. In a 1998 interview, he suddenly leaned in, grabbed a strand of her hair, and put it in his mouth. Aniston looked visibly uncomfortable and wiped her hair with a tissue he handed her.
Despite these moments, Aniston remained professional. She even returned to The Late Show in later years, handling each appearance with her usual composure.
More recently, a clip from one of her later visits resurfaced, showing her giving Letterman a tie as a gift. While the moment was lighthearted, discussions about past interviews have sparked fresh conversations about what was once considered normal in late-night television.