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.
Aniston has always conducted herself with poise, but there was a moment during a specific interview when her discomfort was evident, particularly as Letterman fixated on her legs.
Despite her unease, Letterman persisted. As the discussion progressed, he returned to the topic with another comment: “Your legs, you’ve got something there.” This interaction made fans cringe back then, and it still does today.
To make matters worse, he quickly changed the subject and began probing her about her rumored romance with Vince Vaughn. Letterman even inquired if it was Vaughn’s suggestion for her to “appear naked in the movie.” Taken aback, Aniston paused before skillfully redirecting the question, suggesting that Letterman should have asked Vaughn himself when he was a guest on the show.
Couldn’t resist bringing up Aniston’s legs.
We now know that Jennifer Aniston began a romantic relationship with her co-star Vince Vaughn during the filming of The Break-Up. In a subsequent interview, she shared that he played a significant part in her recovery following her highly publicized divorce.
During a chat with Aniston, David Letterman couldn’t help but comment on her legs. “I can’t get over your legs, I’m telling you. You’ve got something there,” he said.
As the conversation continued, he made another remark that seemed to allude to her legs, stating, “I hope to God somebody at the house is TiVoing this because I can’t stop looking at this shot.” Although it wasn’t entirely clear which shot he was referring to, Aniston’s uncomfortable reaction indicated it was yet another emphasis on her legs.
This wasn’t the first instance of Letterman making Aniston feel uneasy. In a notorious 1998 interview, he grabbed her neck and playfully sucked on a strand of her hair. Aniston, clearly uncomfortable, used a tissue he offered to wipe her hair.
Since we’re discussing David Letterman’s less-than-stellar moments, is anyone going to bring this up? pic.twitter.com/ZU5wIpsTFg
During a particularly awkward exchange, he handed her a tissue to clean off the saliva, which only added to the discomfort of the situation.
Jennifer Aniston handled it with her usual poise, a quality she’s demonstrated countless times throughout her career. No matter the circumstances, she kept the conversation flowing smoothly.
Even after such an uneasy moment, she made a return to The Late Show, showcasing her ability to rise above even the most cringe-worthy encounters.
Two years after her memorable “leg” incident with Letterman, Jennifer Aniston came back to the show, this time dazzling in a stylish pink party dress that reminded everyone of her beauty.
Clips from that appearance have recently gone viral on social media, but many viewers seem to focus on Jennifer’s legs, missing what she was actually holding.
This time, the Hollywood star had more to offer than just her looks. While she skillfully sidestepped personal inquiries, including one about her relationship with John Mayer, she also took a moment to present the host with a thoughtful gift.
Aniston, who once graced the cover of GQ in just a red, white, and blue necktie, gave the gift to the Late Show host while promoting her film Marley & Me.
“It’s an early Christmas present,” she said with a warm smile.
Letterman quickly removed his current tie and, with Aniston’s assistance, put on a new one. She presented him with the Brooks Brothers tie she had worn on the cover of GQ magazine, proudly stating, “This is a highlight of my career.” Wearing the tie with enthusiasm, Letterman joked, “Funny, the tie said the same thing during the photoshoot.”
“This is thrilling, I’m dressing Dave!” she exclaimed.
When the tie seemed a bit too short, Letterman playfully remarked, “You know what they say about guys with short ties.”
It was a lighthearted moment that left fans in awe of the unexpected exchange.
Although Aniston has never publicly criticized these interactions, it’s evident in hindsight that these moments haven’t aged well. What was once seen as late-night comedy is now igniting a new discussion that’s difficult to overlook.
