David Letterman was long known for his humor and presence as a late-night host, but some of his past interviews have been reconsidered in recent years. One frequently discussed example is a 2006 appearance by Jennifer Aniston, who visited The Late Show to promote her film The Break-Up. Viewers looking back at the segment often note that the tone of the conversation feels different when viewed through today’s standards.
During the interview, Letterman shifted the focus away from the film and made repeated comments about Aniston’s appearance, particularly her legs. Although Aniston remained polite and professional, many viewers noticed that she seemed uncomfortable as the conversation continued. Letterman returned to the same topic multiple times, which added to the uneasy dynamic during the segment.
At one point, he joked about hoping the moment was being recorded at home, which further contributed to the awkwardness of the exchange. He also asked questions about media speculation surrounding her relationship with co-star Vince Vaughn and referenced aspects of the film involving her character, which Aniston tried to redirect toward her work. The interaction has been revisited online as part of broader conversations about interview styles and expectations in past decades.
Another example often discussed occurred in a 1998 appearance, when Letterman unexpectedly leaned in and touched Aniston’s hair during the show. The clip has resurfaced repeatedly, surprising many viewers who had not seen it before. While Aniston handled each situation with grace, these moments highlight how perspectives on media conduct and professional boundaries have evolved, reflecting ongoing conversations about respectful treatment in public interviews.
