For years, late-night host David Letterman was admired for his humor and ability to keep audiences entertained. However, some of his interviews have aged poorly, especially when viewed through today’s cultural lens. A widely discussed example involves a 2006 interview with Jennifer Aniston, who appeared on The Late Show to promote her film The Break-Up.
Instead of focusing on the movie, Letterman repeatedly commented on Aniston’s legs, saying she could only wear her outfit because she had “lovely, well-shaped, muscular, lengthy legs.” Aniston smiled politely, but her discomfort was noticeable. As the interview continued, Letterman circled back to the same topic, telling her, “I can’t get over your legs.”
He then joked that he hoped someone at home was recording the show because he couldn’t stop watching “this shot,” which only added to the awkwardness. He also asked about her rumored relationship with co-star Vince Vaughn and questioned whether it was Vaughn’s idea for her to appear nude in the film. Aniston gently deflected, trying to steer the conversation back to her work. This was not an isolated moment.
In 1998, Letterman once surprised Aniston by grabbing her hair during an interview, a clip that has resurfaced online several times. Viewers today often express shock at how casually the incident unfolded on air. While Aniston remained composed during each appearance, these resurfaced interviews highlight shifting standards regarding how women are treated in media settings and what behavior audiences consider acceptable.