David Letterman was once hailed as the king of late-night television, celebrated for his sharp humor and cultural influence. But as old interviews resurface, some moments—especially those involving female guests—are being reevaluated. One that now draws criticism is Jennifer Aniston’s 2006 appearance on The Late Show, which many viewers find uncomfortable in hindsight.
Aniston was promoting The Break-Up when the interview veered off course. Instead of focusing on her work, Letterman fixated on her appearance, repeatedly commenting on her legs. Though Aniston laughed politely and tried to redirect the conversation, he returned to the subject several times, creating visible discomfort. He later pressed her about rumors involving co-star Vince Vaughn, including an awkward question about nudity in the film.
The exchange felt invasive then and appears even more troubling today. It also wasn’t an isolated incident. A 1998 interview resurfaced years later showing Letterman grabbing Aniston’s neck and sucking on her hair—an act that shocked modern audiences.
While Aniston handled these moments with grace, the clips now fuel broader conversations about how “humor” once excused behavior that wouldn’t be acceptable today.
