David Letterman remains one of the most recognizable figures in late-night television, known for interviews that often blended humor, unpredictability, and discomfort. But as older clips continue resurfacing online, some of those moments are being viewed very differently today—especially his interviews with Jennifer Aniston.
A 2006 appearance by Aniston onThe Late Showhas recently drawn renewed attention, with many viewers revisiting the segment through a modern lens and questioning whether the exchange crossed professional boundaries.Continue Reading 
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