David Letterman was once celebrated as the king of late-night television, known for his sharp wit and ability to keep audiences entertained. However, in today’s cultural climate, not all of his past interviews have aged well. Some of his exchanges, particularly with female guests, are now being reexamined with a more critical eye. One such moment that has resurfaced involves Jennifer Aniston, whose appearance on The Late Show with David Letterman in 2006 left many viewers uncomfortable.
At the time, Aniston was promoting The Break-Up, the romantic comedy she starred in alongside Vince Vaughn, who also co-wrote and produced the film. What started as a routine late-night interview quickly took an awkward turn when Letterman became fixated on Aniston’s legs.
Dressed in a black button-down blouse paired with stylish black shorts, Aniston looked effortlessly chic. However, instead of focusing on her work, Letterman’s attention was elsewhere.
“That’s a tremendous outfit,” he commented, before quickly adding, “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 remark left Aniston visibly taken aback. Ever the professional, she laughed it off, brushing it aside by casually explaining that she had chosen shorts simply because of the warm weather.
But Letterman wasn’t done.
As their conversation continued, he circled back to the topic again, saying, “Your legs, you’ve got something there.” The moment was uncomfortable then—and even more cringeworthy when viewed today.
If that weren’t enough, the interview took another unexpected turn when Letterman pressed Aniston about her rumored relationship with Vince Vaughn. He even asked whether it was Vaughn’s idea for her to appear naked in the film. Caught off guard, Aniston hesitated before deflecting, suggesting that Letterman should have asked Vaughn that question when he was on the show.
The pattern continued. Later in the conversation, as Aniston spoke about Vaughn, Letterman once again turned the focus back to her legs, saying, “I can’t get over your legs, I’m telling you. You got something there.”
Then came another questionable remark: “I hope to God somebody at the house is TiVoing this because I can’t stop looking at this shot.” While it wasn’t clear exactly what shot he was referring to, Aniston’s uncomfortable expression suggested she knew exactly where the focus had shifted.
This wasn’t the first time Letterman had made Aniston visibly uncomfortable. One of the most infamous incidents occurred during a 1998 interview, when the late-night host grabbed her neck and sucked on a strand of her hair. Aniston, clearly unsettled, pulled away and awkwardly wiped her hair with the tissue Letterman handed her.
