David Letterman’s question that left Jennifer Aniston very uncomfortable

David Letterman was once hailed as the undisputed king of late-night television. His sharp wit, irreverent humor, and ability to connect with guests made The Late Show with David Letterman a fixture in American homes for decades. However, as the years have gone by, the cultural lens through which we view entertainment has shifted dramatically. The once-lauded figure is now being reexamined, and not all of his past interviews are aging gracefully. One such interview—his interaction with actress Jennifer Aniston in 2006—has recently resurfaced, drawing widespread attention for all the wrong reasons. What was once considered an innocuous, comedic moment has become the subject of discomfort and reflection, highlighting the changing attitudes toward gender, respect, and consent in media.

The Context of the Interview
In 2006, Jennifer Aniston was at a high point in her career. She had already established herself as a beloved TV star through Friends, and was now transitioning into film with roles like the one in The Break-Up, a romantic comedy co-starring Vince Vaughn. Aniston was a tabloid staple, with her personal life under constant public scrutiny, especially following her high-profile split from Brad Pitt. Her appearance on The Late Show was a standard promotional visit—an opportunity to plug her new film and chat with Letterman, a TV legend

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