The David Letterman Interview That Made Jennifer Aniston Squirm

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The David Letterman Moment That Made Jennifer Aniston Uncomfortable

David Letterman, once a late-night legend, is now facing renewed scrutiny over some of his past interviews—especially with female guests. One awkward moment that’s resurfaced involves Jennifer Aniston’s 2006 appearance on The Late Show.

Aniston was there to promote her film The Break-Up, but things took an uncomfortable turn when Letterman shifted focus to her legs, making the exchange feel less like an interview and more like an awkward encounter. What was once brushed off as humor is now being reevaluated in a more critical light.

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