David Letterman, a well-known figure in late-night television, is remembered for his wit, but some of his past interviews have sparked new conversations about their appropriateness. A particular encounter with Jennifer Aniston in 2006 on The Late Show has recently resurfaced, drawing attention for its uncomfortable moments.
Aniston appeared on the show to promote her film The Break-Up. However, the interview took an awkward turn when Letterman repeatedly focused on her legs, complimenting them extensively. The camera even zoomed in on them, adding to Aniston’s visible discomfort. Despite her attempts to lighten the mood by explaining she wore shorts due to the heat, Letterman continued to bring up her legs throughout the conversation.
Beyond the focus on her appearance, Letterman also pressed Aniston about her rumored relationship with co-star Vince Vaughn and questioned her about a supposed nude scene in the movie. This was not the first time Aniston experienced discomfort during a Letterman interview; an infamous 1998 incident involved him grabbing her neck and sucking on her hair.
Despite these challenging interactions, Aniston consistently handled herself with grace and composure, even returning to The Late Show for future appearances. In a later visit promoting Marley & Me, she brought Letterman a thoughtful gift—the Brooks Brothers tie she wore on her GQ cover—creating a playful moment that contrasted with past awkwardness. While Aniston has never publicly criticized these encounters, many now view them differently, highlighting a shift in how celebrity interviews are perceived.
