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.

While Aniston always handled herself with grace, even she couldn’t hide her discomfort during a particular interview where Letterman seemed fixated on her legs.

But Letterman wouldn’t let it go. As the conversation moved on, he circled back with another remark: “Your legs, you’ve got something there.” The exchange left fans cringing then — and even more so now.

As if that wasn’t uncomfortable enough, he quickly shifted gears and began pressing her about her rumored relationship with Vince Vaughn. Letterman also pressed Aniston on whether it was Vaughn’s idea for her to ”appear naked in the movie.” Caught off guard, Aniston hesitated before deflecting, suggesting that Letterman should have asked Vaughn that question when he was on the show.

Couldn’t resist bringing up Aniston’s legs
Today, we know that Aniston started dating her co-star Vince Vaughn while filming The Break-Up. In a later interview, she revealed that he played a crucial role in helping her heal after her highly publicized divorce.

While speaking about Vaughn, Letterman couldn’t resist bringing up Aniston’s legs. ”I can’t get over your legs, I’m telling you. You got something there,” he remarked.

Later in the conversation, he made another comment that seemed to reference them, saying, ”I hope to God somebody at the house TiVoing this because I can’t stop looking at this shot.” While it wasn’t entirely clear what shot he meant, Aniston’s uncomfortable expression suggested it was yet another focus on her legs.

And this wasn’t the first time Letterman made Aniston visibly uncomfortable. In a now-infamous 1998 interview, he grabbed her neck and sucked on a strand of her hair. Aniston, visibly uneasy, wiped her hair with a tissue Letterman handed her.

since we’re talking about david letterman being awful.. is anyone ever going to address this? pic.twitter.com/ZU5wIpsTFg

— ruby (@ifibeIieve) February 14, 2021

He then handed her a tissue to wipe off the saliva, adding to the awkwardness of the exchange.

Aniston handled it with grace, as she has so many times throughout her career. Known for maintaining her composure no matter the situation, she managed to keep the conversation going.

Even after such an uncomfortable moment, she later returned to The Late Show, proving once again that she could rise above even the most awkward encounters.

Two years after her infamous ”leg” moments with Letterman, Jennifer Aniston returned to the show, this time wearing a chic pink party dress that once again reminded viewers just how stunning she was.

Images from the clip have gone viral on social media recently, but most people seem to focus on Jennifer’s legs and overlook what she’s actually holding in her hand.

Because this time, the Hollywood icon had more than just her looks on display. While the actress was busy trying to dodge personal questions, including one about her relationship with John Mayer, she also took a moment to present the host with a thoughtful gift.

Aniston, who had graced the cover of GQ wearing nothing but 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 wasted no time in taking off his current tie and putting on the new one with Aniston’s help. She handed him the Brooks Brothers tie she wore on the cover of GQ magazine, saying, “This is a highlight of my career.” Letterman, wearing the tie with pride, joked, “Funny, the tie said the same thing during the photoshoot.”

”This is exciting, I’m dressing Dave!” she exclaimed.

When the tie appeared a little too short, Letterman quipped, ”You know what they say about guys with short ties.”

It was a playful moment, and fans couldn’t help but gasp at the surprising gesture.

While Aniston has never spoken out against these encounters, looking back, it’s clear these moments haven’t aged well. What was once dismissed as late-night humor is now sparking a new conversation — one that’s hard to ignore.