David Letterman was once celebrated as a late-night television icon, known for his wit and charm. However, not all of his interviews have aged well, particularly when viewed through the lens of modern sensibilities

One such encounter involved Hollywood star Jennifer Aniston, which, at first, appeared to be just another typical talk-show exchange. But revisiting it today, it’s hard to ignore how awkward and uncomfortable it became.

A recently resurfaced clip of Jennifer Aniston and David Letterman has reignited discussions about one of the most cringe-worthy moments on The Late Show. The interview, which took place in 2006, saw Aniston promoting her romantic comedy The Break-Up, co-starring Vince Vaughn. But the conversation quickly took an uncomfortable turn when Letterman became fixated on Aniston’s legs.

Wearing a black blouse paired with black shorts, Aniston unintentionally became the subject of Letterman’s admiration. He couldn’t help but repeatedly compliment her legs, while the cameraman zoomed in to emphasize them.

“That’s a tremendous outfit,” Letterman said, 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.”

Aniston, clearly uncomfortable, tried to downplay his remarks with a nervous laugh, explaining that she had chosen to wear shorts due to the heat. Despite her attempts to redirect the conversation, Letterman insisted on returning to her legs, saying, “Your legs, you’ve got something there.” It left viewers cringing at the awkwardness of the situation, then and now.

As if the comments about her legs weren’t enough, Letterman then shifted to a more personal topic—her rumored relationship with co-star Vince Vaughn. He bluntly asked if it had been Vaughn’s idea for her to “appear naked in the movie.” Caught off guard, Aniston deflected by suggesting that Letterman should ask Vaughn himself when he was next on the show.

But Letterman wasn’t finished. He again commented on Aniston’s legs, saying, “I can’t get over your legs, I’m telling you. You got something there.” Later in the conversation, he referred to the shot of her in the studio, adding, “I hope to God somebody at the house TiVoing this because I can’t stop looking at this shot.” Once again, it wasn’t clear which shot he meant, but Aniston’s uncomfortable reaction suggested it was yet another focus on her legs.

This wasn’t the first time Letterman made Aniston visibly uneasy. In an infamous 1998 interview, he grabbed her neck and sucked on a strand of her hair. Aniston, clearly disturbed, wiped her hair with a tissue that Letterman handed her. He then casually remarked, “You know what they say about guys with short ties,” as if attempting to ease the tension. But the situation only added to the awkwardness of the moment.

Despite the discomfort, Aniston handled both incidents with grace, maintaining her composure in front of the cameras. Known for her poise in difficult situations, she continued the interviews, even returning to The Late Show two years later.

In 2008, Aniston made another appearance on The Late Show, this time wearing a chic pink dress that once again emphasized her stunning looks. But this time, fans paid less attention to her appearance and more to her thoughtful gesture during the interview. Aniston, who had graced the cover of GQ wearing only a necktie, presented Letterman with a gift—a Brooks Brothers tie she had worn on the magazine cover.

“It’s an early Christmas present,” she smiled, as she handed him the tie. Letterman promptly removed his current tie and wore the new one with pride. They joked about the moment, and Aniston exclaiming, “This is exciting, I’m dressing Dave!” added a playful touch to the interview.

While Aniston has never publicly addressed these uncomfortable encounters, looking back, it’s clear that they haven’t aged well. What was once considered typical late-night banter is now sparking new discussions about respect and boundaries, especially in light of Aniston’s grace under pressure.

Today, it’s hard to dismiss the awkwardness of those moments, and they stand as a reminder of how far the conversation around gender and respect in the media has come.

Though she has always maintained her composure, these interviews now invite us to reflect on how public figures—especially women—are treated and the nature of humor in late-night television. Aniston’s ability to rise above the discomfort of those moments makes her even more admirable, but the reality is that these instances, now revisited, highlight how the boundaries of appropriate behavior have evolved.