David Letterman has long been recognized as a pioneer of late-night television, celebrated for his quick wit and influence on the genre. But as many iconic moments from his show resurface online, some interviews are being viewed in a new light—and not all are standing the test of time.
One such moment involves actress Jennifer Aniston, who appeared on The Late Show with David Letterman in 2006 to promote her film The Break-Up. At the time, the interview seemed like another celebrity chat. But in recent years, clips have been shared widely on social media, prompting viewers to reflect on the tone and focus of the conversation.
An Interview That Left Viewers Divided
During the interview, Aniston wore a stylish black outfit consisting of a blouse and shorts—perfectly appropriate for the summer heat. Letterman complimented her appearance, with comments focused on her legs. While many late-night interviews include light banter, some viewers have noted that the repeated focus on her appearance made the moment feel more awkward than playful.
Aniston, ever professional, responded with her signature humor and grace. She brushed off the remarks, attributing her choice of attire to the warm weather. However, the host returned to the subject more than once, which some viewers now say overshadowed the reason she was there—to talk about her work.
Continue reading on next page…