David Letterman has long been hailed as a trailblazer in late-night television, known for his sharp humor and lasting impact on the format. However, as many memorable moments from his show resurface online, some interviews are being reconsidered—and not all are aging well.
One notable example features actress Jennifer Aniston during her 2006 appearance on The Late Show with David Letterman to promote her film The Break-Up. At the time, the interview appeared to be a routine celebrity conversation. But in recent years, clips have circulated widely on social media, leading viewers to reconsider the tone and focus of the exchange.
An Interview That Sparked Mixed Reactions
Throughout the interview, Aniston wore a chic black outfit—blouse and shorts—that suited the summer weather. Letterman complimented her look, often remarking on her legs. While playful banter is typical in late-night shows, some viewers have since pointed out that the repeated emphasis on her appearance made the interaction feel awkward rather than lighthearted.
Aniston handled it with professionalism and wit, joking that her outfit was simply due to the warm weather. Yet Letterman returned to the subject multiple times, which some feel detracted from the main purpose of the interview—to discuss her work.
