David Letterman’s Question That Left Jennifer Aniston Uncomfortable: Revisiting the Uneasy Interview

David Letterman, once hailed as the king of late-night television, was renowned for his sharp wit and his ability to entertain millions of viewers. However, in today’s cultural climate, not all of his past interviews with Hollywood celebrities have aged well. Some of his encounters, particularly those involving female celebrities, are now being reexamined with a more critical eye. One such moment that has resurfaced involves Jennifer Aniston, whose appearance on The Late Show with David Letterman in 2006 left many viewers uncomfortable.

At the time, Aniston was promoting The Break-Up, a romantic comedy she starred in alongside Vince Vaughn, who also co-wrote and produced the film. What started as a typical late-night interview quickly became an awkward spectacle when Letterman became fixated on Aniston’s legs.

Aniston, dressed in a sleek black button-down blouse and stylish black shorts, looked effortlessly chic. However, instead of discussing her role in the film or her career, Letterman’s attention was elsewhere.

“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.”

The comment immediately left Aniston visibly taken aback. Ever the professional, she laughed it off, brushing the remark aside by explaining that she had simply chosen shorts due to the warm weather.

However, Letterman wasn’t finished.

As the conversation continued, he circled back to the topic, saying, “Your legs, you’ve got something there.” This moment, once awkward, feels even more cringeworthy when viewed through today’s lens, especially considering the ongoing discussions surrounding sexual harassment in media and the changing standards in Hollywood interviews.

The conversation took yet another uncomfortable 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, deflecting the question by suggesting that Letterman should have asked Vaughn himself when he was a guest on the show.

The tension continued. As Aniston spoke about Vaughn, Letterman once again shifted the conversation back to her legs, saying, “I can’t get over your legs. You’ve got something there.”

He then made another questionable comment: “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 which shot he was referring to, Aniston’s uncomfortable expression suggested she understood where the focus had shifted.

This wasn’t the first time Letterman had made Aniston visibly uncomfortable. One of the most infamous moments 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 a tissue that Letterman handed her. The clip from that 1998 interview continues to spark outrage every time it resurfaces, drawing attention to the power dynamics in entertainment and the way female celebrities have been treated in Hollywood media interviews.

In 2021, a viral tweet reignited these discussions when a user shared a video of this incident, captioning it: “Since we’re talking about David Letterman being awful… is anyone ever going to address this?”

When viewers watch the footage today, many are shocked by how invasive the moment was. Letterman handed Aniston a tissue after putting his saliva in her hair, as if expecting her to clean up after the bizarre interaction. This incident has raised questions about the media ethics that once prevailed in late-night television and how those standards have shifted, especially with the rise of the MeToo movement.

Despite these uncomfortable encounters, Aniston continued to make appearances on The Late Show. She handled each awkward 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 the tie 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 seemed lighthearted, it underscored a recurring pattern in Letterman’s interviews with female celebrities—comments that, in today’s climate, would be considered inappropriate, particularly in light of changing perceptions about cultural shifts in entertainment.

Though Jennifer Aniston has never publicly addressed these interactions, they are now viewed through a new lens. What was once dismissed as late-night humor is now part of the broader conversation about how women in Hollywood have long been treated in the media. As these clips continue to resurface, audiences are questioning what was once considered acceptable in celebrity interviews and recognizing the challenges that female celebrities continue to face in the entertainment industry.

While Aniston handled each situation with poise, it’s impossible to ignore how many of these moments—especially those involving David Letterman—have aged poorly.