David Letterman’s interview style was once considered bold and entertaining, but many past moments are now viewed more critically. A resurfaced clip from 2006 featuring Jennifer Aniston has reignited the debate about awkward celebrity interviews.
During her appearance on “The Late Show” to promote “The Break-Up,” Aniston found herself in an awkward situation when Letterman focused on her appearance – specifically, her legs. Despite her attempts to steer the conversation toward her film, Letterman repeatedly commented on her outfit and physique, leading to an uncomfortable conversation. He later pressed her with rumors about her co-star Vince Vaughn, surprising her even more.
This wasn’t the first time Aniston encountered awkward situations on Letterman’s show. A clip from 1998 shows him unexpectedly grabbing her hair – an interaction that today seems more intrusive than playful. Although Aniston handled these moments with aplomb, they highlight how often women in Hollywood were subjected to inappropriate comments.
As media norms evolve, interviews like this remind us how much has changed – and how much the industry still has to do to foster more respectful conversations.