David Letterman’s question that left Jennifer Aniston

A Legacy Reconsidered

David Letterman was once praised for his late-night charm,

but some interviews have not aged well. Critics now point to

moments that feel uncomfortable when viewed today.

The 2006 Interview

During a 2006 appearance on The Late Show to promote

The Break-Up, Jennifer Aniston became the focus of attention

for reasons unrelated to her film. Letterman repeatedly commented

on her appearance, especially her legs, while the camera zoomed in.

Awkward Moments

Letterman told her, “That’s a tremendous outfit…

because you have tremendous legs. Fantastic legs.”

He later added, “Your legs, you’ve got something there.”

Aniston laughed it off, saying she wore shorts because

of the heat, but appeared visibly uncomfortable.

Lasting Impact

Resurfaced clips have reignited criticism, with many arguing

these moments crossed boundaries. What once passed as

humor now fuels a broader discussion about respect and conduct in late-night television.

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