David Letterman’s question that left Jennifer Aniston very uncomfortable

David Letterman was once hailed as the king of late-night television, known for his sharp wit and humor. However, many of his past interviews are now being reexamined, particularly his uncomfortable exchanges with female guests. One such moment that has resurfaced involves Jennifer Aniston’s 2006 appearance on The Late Show, which left viewers uneasy.

Aniston, promoting her film The Break-Up, appeared stylish in a black blouse and shorts. But instead of focusing on her movie, Letterman repeatedly commented on her legs, saying, “That’s a tremendous outfit… because you have tremendous legs.” Aniston, clearly caught off guard, laughed politely and moved on, but the host continued to bring up her appearance.