David Letterman’s question that left Jennifer Aniston very uncomfortable

A resurfaced clip from a 2006 episode of The Late Show is sparking fresh debate about David Letterman’s interviewing style—this time involving Jennifer Aniston. While promoting The Break-Up, Aniston found herself in an unexpectedly uncomfortable moment when Letterman fixated on her outfit and legs, offering comments that felt more awkward than amusing.

Aniston tried to laugh it off, but the exchange has aged poorly in today’s media climate, where viewers are far more aware of power dynamics and inappropriate on-air behavior. What was once brushed off as late-night humor is now being revisited as an example of how casually women in Hollywood were objectified—even in front of millions.