David Letterman was once celebrated as a late-night icon, praised for his wit and charm. But in hindsight, not all of his interviews have aged well, at least according to critics.
One episode that stands out involved Hollywood star Jennifer Aniston. At first glance, it seemed like a routine talk-show appearance—but watching it today, it feels uncomfortable.
In 2006, Aniston appeared on The Late Show with David Letterman to promote The Break-Up, her romantic comedy with Vince Vaughn. From the start, the interview took an awkward turn as Letterman repeatedly focused on Aniston’s legs.
Dressed in a black button-down blouse and black shorts, she quickly became the center of Letterman’s admiration. He praised her legs over and over, and the cameraman even zoomed in to highlight them.
“That’s a tremendous outfit,” he said. “And the reason it’s tremendous is because you have tremendous legs. Fantastic legs. You can only wear that if you have lovely, well-shaped, muscular, lengthy legs.”
Aniston, visibly taken aback, laughed and explained she had worn shorts simply because of the heat, trying to downplay the comments.
While Aniston always carried herself with grace, even she couldn’t completely hide her discomfort during the 2006 interview, as Letterman repeatedly fixated on her legs.
As the conversation moved on, he circled back:
“Your legs, you’ve got something there.”
Fans cringed then—and even more so today.
The tension increased when Letterman shifted to personal questions about her rumored relationship with Vince Vaughn, asking whether it had been his idea for her to “appear naked in the movie.” Aniston, caught off guard, deflected gracefully, suggesting he should have asked Vaughn directly.
Even as she spoke about Vaughn—who would later become her partner during filming—Letterman returned to her legs:
“I can’t get over your legs, I’m telling you. You got something there.”
At one point, he added:
“I hope to God somebody at the house TiVoing this because I can’t stop looking at this shot.”
Although unclear which shot he meant, Aniston’s expression suggested it was yet another reference to her legs.
This wasn’t the first time Letterman made her visibly uncomfortable. In a 1998 interview, he grabbed her neck and sucked on a strand of her hair. Aniston, uneasy, wiped it with a tissue he handed her, which only added to the awkwardness. Yet she maintained her composure and kept the conversation going.
Proving her professionalism, Aniston returned to The Late Show two years later, wearing a chic pink party dress that reminded viewers of her poise and style. This time, she brought more than just her looks—she presented Letterman with a thoughtful gift while promoting Marley & Me: the Brooks Brothers tie she had worn for a GQ cover shoot.
“It’s an early Christmas present,” she said with a smile.
Letterman immediately removed his own tie and, with Aniston’s help, put on the Brooks Brothers tie she had worn for her GQ cover shoot.
“This is a highlight of my career,” she said, smiling.
Letterman, wearing it proudly, joked:
“Funny, the tie said the same thing during the photoshoot.”
“This is exciting, I’m dressing Dave!” Aniston exclaimed.
When the tie appeared slightly short, Letterman quipped,
“You know what they say about guys with short ties.”
The playful exchange offered a lighthearted moment, leaving fans charmed by the gesture.
Yet, looking back at her earlier encounters with Letterman, it’s clear that not all moments aged as well. What was once shrugged off as late-night humor now prompts renewed discussion—and a critical reexamination of how guests were treated.
