David Letterman was once considered the king of late-night television, celebrated for his sharp humor and engaging presence. His interviews drew millions of viewers, and his wit made him a household name. However, looking back, not all of his on-air moments have aged gracefully, especially when viewed through today’s lens. Critics and fans alike have begun reexamining some of his past interactions, and one in particular involving actress Jennifer Aniston has resurfaced, sparking renewed discussions about boundaries and respect in celebrity interviews.
At first glance, Aniston’s 2006 appearance on The Late Show with David Letterman seemed like any other celebrity interview. She was there to promote The Break-Up, a romantic comedy where she starred alongside Vince Vaughn, who also co-wrote and produced the film. Dressed in a stylish black blouse and matching shorts, Aniston took her seat, likely expecting a casual conversation about her latest project. However, things took an awkward turn almost immediately.
Letterman quickly fixated on Aniston’s legs, repeatedly complimenting them in a way that made many viewers uncomfortable even at the time. His fascination with her outfit was less about fashion and more about her physical appearance. “That’s a tremendous outfit,” he commented, 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.” While meant to be playful, his remarks bordered on excessive, and the cameraman reinforced the moment by zooming in on Aniston’s legs, making the focus even more uncomfortable.
Aniston, clearly caught off guard, tried to laugh it off, explaining that she wore shorts simply because of the hot weather. Despite her attempt to steer the conversation elsewhere, Letterman continued. As the segment progressed, he circled back again, saying, “Your legs, you’ve got something there.” What may have once passed as light-hearted banter now feels invasive, especially as Aniston’s unease becomes more apparent.
The discomfort didn’t end there. Letterman soon shifted gears, pressing Aniston about her rumored relationship with Vince Vaughn, asking if it had been Vaughn’s idea for her to appear naked in the film. Visibly unsettled, Aniston tried to deflect, suggesting Letterman should have asked Vaughn that question when he was on the show. Throughout the exchange, she maintained her trademark grace, but the tension was palpable.
As the conversation returned to Vaughn, Letterman again couldn’t resist commenting on Aniston’s legs. “I can’t get over your legs, I’m telling you. You got something there,” he remarked yet again. Then came another comment that left viewers cringing. Referencing a particular camera shot, Letterman quipped, “I hope to God somebody at the house is TiVoing this because I can’t stop looking at this shot.” While he didn’t specify which shot, the implication seemed clear. Aniston’s expression, tinged with discomfort, spoke volumes.
This wasn’t the first time Letterman made headlines for his interactions with Aniston. In a 1998 interview that remains infamous, Letterman suddenly grabbed Aniston’s neck and sucked on a strand of her hair. The moment was bizarre, to say the least, and Aniston’s reaction—wiping her hair with a tissue Letterman handed her—made it clear she was uncomfortable. The incident resurfaced on social media years later, with many questioning how such behavior was ever acceptable on national television.
Despite these moments, Aniston handled herself with poise, as she has done throughout her career. She didn’t let the awkwardness derail the interviews and somehow managed to keep the conversation going. Remarkably, she returned to The Late Show in 2008, just two years after the “leg” episode, proving once again that she could rise above even the most uncomfortable encounters.
During that return visit, Aniston wore a stunning pink party dress that captured viewers’ attention once more. However, this time, it wasn’t just her appearance that had people talking. She brought a thoughtful gift for Letterman—a red, white, and blue Brooks Brothers tie, the same one she had worn on the cover of GQ magazine. “It’s an early Christmas present,” she said with a smile, presenting the tie while promoting her film Marley & Me.
Letterman, amused, immediately removed his own tie and allowed Aniston to help him put on the new one. “This is a highlight of my career,” she joked, referencing the memorable photoshoot. Letterman quipped back, “Funny, the tie said the same thing during the photoshoot.” The exchange was lighthearted, and Aniston exclaimed, “This is exciting, I’m dressing Dave!” When the tie appeared a bit short, Letterman made another playful comment: “You know what they say about guys with short ties.” It was a moment of humor that fans enjoyed, though some couldn’t help but recall the earlier, more awkward exchanges between the two.
Although Aniston has never publicly criticized these encounters, it’s clear that times have changed. What once passed as late-night entertainment is now viewed with a more critical eye. The resurfaced clips have prompted new conversations about the expectations placed on female celebrities during interviews and the fine line between humor and discomfort.
Looking back, it’s easy to see why moments like these no longer sit well with many viewers. The shift in societal norms has brought greater awareness to how women are treated in media and public spaces. While Aniston’s professionalism never wavered, these interactions serve as a reminder of the challenges many actresses have faced—and continue to face—when simply trying to promote their work.
As we reflect on these past moments, it’s important to recognize both how far we’ve come and how much further we still need to go. Conversations like this help shine a light on the importance of respect and boundaries, even in the world of entertainment.
