David Letterman built his legacy on sharp comedy and unpredictable interviews, but time has changed how many of his on-air moments are perceived. One clip that resurfaces often is Jennifer Aniston’s 2006 appearance on The Late Show, an interview that felt awkward even then and feels far more uncomfortable now. Aniston arrived to promote The Break-Up, relaxed and smiling, but Letterman immediately fixated on her appearance—especially her legs—returning to the topic repeatedly even when she tried to shift the conversation back to her film. Her polite smile couldn’t hide the tension.
As the interview continued, the questions grew more personal. Letterman joked about Vince Vaughn encouraging her to appear nude in the movie and commented on a camera shot he “couldn’t stop looking at,” catching Aniston off guard and making the atmosphere even more uneasy. This wasn’t an isolated incident: a 1998 clip frequently goes viral because Letterman pulled Aniston toward him, took a strand of her hair, and put it in his mouth—an act that left her visibly uncomfortable and still shocks viewers today. These moments now stand as reminders of how women in Hollywood were often placed in difficult, invasive situations during live television.
Despite these encounters, Aniston continued to appear on the show and always handled the awkwardness with remarkable professionalism. She stayed composed, redirected conversations with humor, and never publicly criticized Letterman—something few actresses felt empowered to do in the early 2000s while promoting major films. Even in later interviews, such as her 2008 appearance for Marley & Me, the tone remained similar: lighter at times, but still marked by comments about her appearance or innuendo.
Viewed through a modern lens, these interviews reflect a broader pattern from that era, when many actresses—Anne Hathaway, Lindsay Lohan, Britney Spears, Paris Hilton, and others—faced invasive questions and jokes on national TV. What stands out today is not Letterman’s humor, but Aniston’s grace. Her dignity, patience, and resilience have aged far better than the clips themselves, highlighting how much she navigated—and how much media culture has shifted since then.