David Letterman has long been celebrated as a late-night television legend, known for his quick wit and sharp humor. However, some of his interviews, particularly with Jennifer Aniston, have not aged well and have recently resurfaced, sparking discussions about the boundaries of humor and respect on television.

One such interview took place in 2006 when Jennifer Aniston appeared on The Late Show to promote the romantic comedy The Break-Up, in which she starred alongside Vince Vaughn. While most of the conversation was typical late-night banter, things quickly took an uncomfortable turn when Letterman began to focus on Aniston’s appearance — specifically her legs.

As she sat in a black button-down blouse and black shorts, Letterman seemed to be mesmerized by her legs. He couldn’t help but compliment them multiple times during their conversation. “That’s a tremendous outfit,” he said before 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 caught off guard by the constant praise of her physical appearance, tried to brush it off with a light-hearted comment about wearing shorts because of the heat. But Letterman wasn’t done. He circled back, commenting again, “Your legs, you’ve got something there.” This awkward focus on her body was enough to leave both Aniston and the audience uncomfortable.

As if this weren’t enough, Letterman switched gears to press Aniston about her rumored relationship with co-star Vince Vaughn, even asking if it was his idea for her to appear nude in the film. Caught off guard, Aniston skillfully deflected the question by suggesting that Letterman ask Vaughn that when he appeared on the show next.

Despite the tension, Letterman couldn’t resist another remark about her legs. “I can’t get over your legs,” he said, further unsettling Aniston. His attempts to steer the conversation back to her personal life and relationships only added to the discomfort. Later in the conversation, Letterman commented about how he hoped someone was recording the show because, “I can’t stop looking at this shot.” While it wasn’t clear which shot he was referring to, it was evident from Aniston’s reaction that she was not pleased with the attention being focused on her body.

This wasn’t the first time Aniston had been made uncomfortable by Letterman. In a now-infamous 1998 interview, he had grabbed her neck and sucked on a strand of her hair, prompting Aniston to wipe her hair with a tissue he handed her. While she maintained her composure both times, these moments now stand out as troubling examples of the host crossing boundaries in the name of humor.

Despite these awkward incidents, Aniston returned to The Late Show two years later. This time, she wore a chic pink dress and once again captivated the audience with her grace and elegance. During this appearance, Aniston, while still facing personal questions, took the opportunity to present Letterman with an early Christmas gift: a Brooks Brothers tie she had worn for a GQ cover shoot. As she handed it to him, she said with a smile, “This is a highlight of my career.” Letterman wasted no time in putting the tie on, even joking about the size of the tie when it appeared a bit short. This playful moment was a stark contrast to the previous, more uncomfortable interactions, showing Aniston’s ability to stay poised despite the awkwardness of past encounters.

While these more lighthearted moments seem to be in stark contrast to the previous tense ones, the history of Letterman’s treatment of Aniston remains a topic of conversation. As social standards around respect and boundaries in media evolve, many are revisiting these moments from the past, questioning what was once deemed acceptable humor. While Aniston has never publicly criticized these moments, the way they have aged raises important questions about how we view celebrity interviews, consent, and the power dynamics at play.

In the years since, both Aniston and Letterman have moved on, but these resurfaced moments now act as a reminder of how far public conversations about respect and boundaries have come. Whether or not Letterman intended to make Aniston uncomfortable, it’s clear that these moments haven’t stood the test of time in the eyes of modern audiences. What was once seen as playful, off-the-cuff humor is now viewed in a different light, sparking conversations about the importance of mutual respect in all forms of media.