Dressed in a black button-down blouse paired with stylish black shorts, Aniston looked effortlessly chic. However, instead of focusing on her work, Letterman’s attention was elsewhere.

“That’s a tremendous outfit,” he commented, before quickly 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.”

The remark left Aniston visibly taken aback. Ever the professional, she laughed it off, brushing it aside by casually explaining that she had chosen shorts simply because of the warm weather.

But Letterman wasn’t done.

As their conversation continued, he circled back to the topic again, saying, “Your legs, you’ve got something there.” The moment was uncomfortable then—and even more cringeworthy when viewed today.

If that weren’t enough, the interview took another unexpected turn when Letterman pressed Aniston about her rumored relationship with Vince Vaughn. He even asked whether it was Vaughn’s idea for her to appear naked in the film. Caught off guard, Aniston hesitated before deflecting, suggesting that Letterman should have asked Vaughn that question when he was on the show.

The pattern continued. Later in the conversation, as Aniston spoke about Vaughn, Letterman once again turned the focus back to her legs, saying, “I can’t get over your legs, I’m telling you. You got something there.”

Then came another questionable remark: “I hope to God somebody at the house is TiVoing this because I can’t stop looking at this shot.” While it wasn’t clear exactly what shot he was referring to, Aniston’s uncomfortable expression suggested she knew exactly where the focus had shifted.

This wasn’t the first time Letterman had made Aniston visibly uncomfortable. One of the most infamous incidents occurred during a 1998 interview, when the late-night host grabbed her neck and sucked on a strand of her hair. Aniston, clearly unsettled, pulled away and awkwardly wiped her hair with the tissue Letterman handed her.

Clips of this incident have resurfaced over the years, sparking outrage each time. A viral tweet from 2021 reignited discussions, with a user sharing the video along with the caption:

“Since we’re talking about David Letterman being awful… is anyone ever going to address this?”

Watching the footage today, many people are shocked by how invasive the moment was. Letterman handed her a tissue after putting his saliva in her hair, as if expecting her to clean up after the bizarre interaction.

Despite these uncomfortable encounters, Aniston continued to make appearances on The Late Show, handling each moment with the same grace and composure that has defined her career. In 2008, two years after her awkward “legs” interview, she returned to the show, this time wearing a chic pink party dress that once again drew attention to her stunning presence.

While promoting her new film Marley & Me, Aniston brought Letterman a special gift—a Brooks Brothers necktie, identical to the one she wore on the cover of GQ Magazine, where she posed in nothing but the red, white, and blue accessory.

“It’s an early Christmas present,” she said, smiling as she handed him the tie.

Letterman wasted no time, immediately swapping out his own tie for the one Aniston had given him. “Funny, the tie said the same thing during the photoshoot,” he quipped, clearly delighted by the gesture.

Aniston playfully assisted him, laughing, “This is exciting, I’m dressing Dave!”

As he adjusted it, he noticed it looked a little too short. “You know what they say about guys with short ties,” he joked, eliciting gasps and laughter from the audience.

While the moment was lighthearted and fun, it underscored a recurring pattern—Letterman’s interviews with female celebrities often included comments that wouldn’t sit well in today’s cultural climate.

Though Jennifer Aniston has never publicly addressed these interactions, they are now being viewed through a new lens. What was once dismissed as “late-night humor” is now the subject of deeper conversations about how women in Hollywood have long been treated in media interviews.

As these clips continue to resurface, audiences are questioning what was once considered acceptable and acknowledging the challenges that female celebrities have faced in the entertainment industry. While Aniston handled each situation with poise, it’s hard to ignore how many of these moments—especially those with Letterman—have aged poorly.