David Letterman was once celebrated as a late-night television icon, recognized for his humor and charisma. However, in retrospect, not all of his interviews have aged well — at least, not according to critics.
One particular encounter featured Hollywood actress Jennifer Aniston. At first, it appeared to be just another talk-show segment. But looking back now?
Couldn’t help but admire her legs
A resurfaced image of Jennifer Aniston and David Letterman has sparked renewed conversations about one of the most awkward moments on The Late Show.
The 2006 interview occurred when Jennifer Aniston visited The Late Show with David Letterman to promote The Break-Up, a romantic comedy in which she starred alongside Vince Vaughn, who also co-wrote and produced the film.
The interview took an uncomfortable turn right from the beginning when Letterman fixated on Aniston’s legs, continuously complimenting them throughout their chat.
Dressed in a black button-down blouse and black shorts, Aniston quickly became the center of Letterman’s admiration. He couldn’t resist praising her legs, and the cameraman joined in, zooming in to emphasize them.
“That’s a tremendous outfit,” he commented, before reiterating, “and the reason that’s a tremendous outfit is that you have tremendous legs. Fantastic legs. You can only wear that if you have lovely, well-shaped, muscular, lengthy legs.”
The actress, clearly surprised, attempted to downplay the remark, laughing it off by explaining that she wore shorts simply due to the heat.
Although Aniston always maintained her poise, she couldn’t completely mask her unease during a specific interview where Letterman appeared fixated on her legs.
However, Letterman persisted. As the discussion progressed, he returned to the topic with another comment: “Your legs, there’s something there.” This interaction made fans cringe back then — and even more so today.
As if that wasn’t awkward enough, he quickly changed the subject and started questioning her about her rumored romance with Vince Vaughn. Letterman also inquired whether it was Vaughn’s suggestion for her to “appear naked in the film.” Taken aback, Aniston paused before sidestepping the question, implying that Letterman should have directed that inquiry to Vaughn when he was a guest on the show.
Couldn’t help but mention Aniston’s legs
Today, we know that Aniston began dating 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 widely publicized divorce.
While discussing Vaughn, Letterman couldn’t help but bring up Aniston’s legs. “I can’t get over your legs, I’m telling you. You’ve got something there,” he commented.
Later in their chat, he made another remark that seemed to allude to them, saying, “I hope to God somebody at the house 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 uneasy expression indicated it was yet another emphasis on her legs.
This wasn’t the first instance where Letterman made Aniston visibly uncomfortable. In a now-notorious 1998 interview, he grabbed her neck and sucked on a strand of her hair. Aniston, clearly uneasy, wiped her hair with a tissue that Letterman had given her.
Since we’re discussing David Letterman being terrible, is anyone going to bring this up? pic.twitter.com/ZU5wIpsTFg
— Ruby (@ifibeIieve) February 14, 2021
He then offered her a tissue to clean off the saliva, which only added to the awkwardness of the situation.
Aniston managed it with poise, just as she has done countless times in her career. Renowned for her ability to stay composed regardless of the circumstances, she kept the dialogue flowing.
Even after such an uneasy moment, she made a return to The Late Show, demonstrating once more that she could rise above even the most uncomfortable situations.
Two years following her notorious ‘leg’ incidents with Letterman, Jennifer Aniston came back to the show, this time donning a stylish pink party dress that reminded viewers of her stunning beauty.
Clips from the segment have recently gone viral on social media, but many seem to focus on Jennifer’s legs while missing what she was actually holding.
This time, the Hollywood star showcased more than just her appearance. While she was busy sidestepping personal inquiries, including one about her relationship with John Mayer, she also took a moment to give the host a thoughtful gift.
Aniston, who had previously graced the cover of GQ wearing only a red, white, and blue necktie, presented the gift to the Late Show host while promoting her new film, Marley & Me.
“It’s an early Christmas present,” she said with a 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, remarking, “This is a highlight of my career.” Wearing the tie proudly, Letterman joked, “Funny, the tie said the same thing during the photoshoot.”
“This is exciting, I’m dressing Dave!” she exclaimed.
When the tie seemed a bit too short, Letterman quipped, “You know what they say about guys with short ties.”
It was a lighthearted moment, and fans couldn’t help but gasp at the unexpected gesture.
Although Aniston has never publicly criticized these encounters, reflecting on them now, it’s evident that these moments haven’t aged well. What was once seen as late-night humor is now igniting a new discussion — one that’s difficult to overlook.
