David Letterman was once hailed as a master of late-night television, known for his wit and charm. But looking back, not all of his interviews have stood the test of time — at least, not in the eyes of critics.
One encounter, in particular, involved Hollywood star Jennifer Aniston. At first glance, it seemed like just another talk-show moment. But watching it today?
Couldn’t help but praise her legs
A resurfaced photo of Jennifer Aniston and David Letterman has reignited discussions about one of the most uncomfortable moments on The Late Show.
The 2006 interview took place when Jennifer Aniston appeared on The Late Show with David Letterman to promote The Break-Up, a romantic comedy where she starred alongside Vince Vaughn, who also co-wrote and produced the film.
The interview took an awkward turn right from the start when Letterman fixated on Aniston’s legs, repeatedly complimenting them throughout their conversation.
Wearing a black button-down blouse paired with black shorts, Aniston quickly became the focus of Letterman’s admiration. He couldn’t help but praise her legs, and the cameraman followed suit, zooming in to highlight them.
“That’s a tremendous outfit,” he remarked, before doubling down, “and the reason that’s a tremendous outfit is because you have tremendous legs. Fantastic legs. You can only wear that if you have lovely, well-shaped, muscular, lengthy legs”
The actress, clearly taken aback, tried to downplay the comment, laughing it off by saying she had worn shorts simply because of the heat.
While Aniston always handled herself with grace, even she couldn’t hide her discomfort during a particular interview where Letterman seemed fixated on her legs.
But Letterman wouldn’t let it go. As the conversation moved on, he circled back with another remark: “Your legs, you’ve got something there.” The exchange left fans cringing then — and even more so now.
As if that wasn’t uncomfortable enough, he quickly shifted gears and began pressing her about her rumored relationship with Vince Vaughn. Letterman also pressed Aniston on whether it was Vaughn’s idea for her to ”appear naked in the movie.” Caught off guard, Aniston hesitated before deflecting, suggesting that Letterman should have asked Vaughn that question when he was on the show.
