David Letterman built much of his reputation on sharp comedy and unpredictable interviews, but time has changed the way many of those moments are viewed. A clip that repeatedly resurfaces is Jennifer Aniston’s 2006 appearance on The Late Show—an interview that already felt awkward years ago and feels even more uncomfortable now.
Aniston was there to promote her film The Break-Up. She walked onstage looking relaxed, dressed in a simple black blouse and tailored shorts. The conversation started normally, but almost immediately shifted when Letterman focused on her appearance, especially her legs. He complimented her outfit, then made several comments about her “tremendous legs,” circling back to the topic even when she tried to redirect the conversation toward the film. She smiled politely, the way many guests did, but the discomfort was clear.
The interview continued to drift into personal territory. When the topic of Vince Vaughn came up, Letterman joked about whether Vaughn encouraged her to appear nude in the film, catching her off guard. She deflected carefully, trying to steer the conversation back to safer ground. Later, Letterman commented on a camera shot he “couldn’t stop looking at,” leaving viewers to interpret the moment on their own. Aniston kept her composure, but it was difficult to watch even then.
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