David Letterman was long celebrated as a late-night legend known for sharp wit and easy charm. But in hindsight, some of his interviews haven’t aged well in the eyes of critics.
One moment that continues to resurface involves Hollywood star Jennifer Aniston. What seemed like a routine talk-show appearance at the time now feels noticeably uncomfortable to many viewers.
During her 2006 visit to promote The Break-Up, Aniston became the focus of repeated remarks about her legs. Wearing a black blouse and shorts, she tried to laugh off the attention, explaining she dressed that way because of the heat. Still, the exchange has since sparked renewed debate about how the moment played out on late-night television.
