David Letterman’s question that left Jennifer Aniston very uncomfortable

An Old Interview with Jennifer Aniston Raises Eyebrows Today

David Letterman, once a late-night TV icon, is now facing fresh scrutiny over past interviews — especially with female guests.

One moment gaining attention is his 2006 interview with Jennifer Aniston. While promoting The Break-Up, the conversation took an uncomfortable turn when Letterman became oddly focused on Aniston’s legs, making viewers uneasy then — and even more so now.

What once passed as late-night banter is now being reexamined through a more respectful lens.

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