David Letterman’s question that left Jennifer Aniston very uncomfortable

David Letterman was long seen as a late-night icon, but some past interviews now feel uncomfortable in hindsight. One moment with Jennifer Aniston has resurfaced, drawing fresh criticism.

During her 2006 appearance promoting The Break-Up, the conversation quickly turned awkward as Letterman repeatedly focused on her legs. While he praised her outfit, his comments became excessive, with the camera even zooming in. Aniston, caught off guard, tried to laugh it off, saying she chose the outfit because of the heat—but the moment has since been viewed very differently.