Jennifer Aniston Reacts to David Letterman’s Unexpected Question in Resurfaced Interview

David Letterman was once hailed as a late-night legend, admired for his sharp humor and laid-back charisma. But in hindsight, not all of his interviews have stood the test of time — especially when viewed through today’s lens of awareness and respect. One particular moment involving Jennifer Aniston has recently resurfaced, reminding viewers just how uncomfortable things got during what should’ve been a typical talk-show appearance.

The Attention on Her Legs

A resurfaced clip from a 2006 interview between Aniston and Letterman is once again making the rounds — and not for the right reasons. At the time, Aniston was promoting The Break-Up, her romantic comedy with Vince Vaughn. But what started as light conversation quickly turned into one of the show’s most cringeworthy segments.

Wearing a black blouse with black shorts, Aniston soon became the subject of Letterman’s fixation — particularly her legs. He repeatedly complimented them, while the camera awkwardly zoomed in.
“That’s a tremendous outfit,” he said, “And the reason it’s tremendous is because you have tremendous legs. Fantastic legs.” He added, “You can only wear that if you have lovely, well-shaped, muscular, lengthy legs.”

Aniston, clearly unsettled, tried to brush it off with a nervous laugh, mentioning she wore shorts because of the heat. Despite her attempts to steer the conversation elsewhere, Letterman returned to the subject again: “Your legs, you’ve got something there.” The tension was evident, and many viewers — both then and now — found the moment deeply uncomfortable.

Crossing into Personal Territory
As if the commentary on her appearance wasn’t enough, Letterman shifted to more personal ground. He bluntly asked Aniston whether it was Vince Vaughn’s idea for her to appear nude in the film. Visibly caught off guard, she dodged the question with humor, suggesting Letterman ask Vaughn himself next time he appeared on the show.

But Letterman kept going. He again returned to her legs, repeating, “I can’t get over your legs.” Later in the conversation, he referenced the camera angle showing her on-screen and said, “I hope to God somebody’s TiVoing this because I can’t stop looking at this shot.” While unclear what exactly he meant, Aniston’s strained expression said enough.

Not Their First Awkward Exchange
This wasn’t the first time Letterman pushed boundaries with Aniston. In a now-infamous 1998 appearance, he leaned over, grabbed a strand of her hair, and put it in his mouth. Aniston, visibly disturbed, wiped her hair with a tissue he handed her, while Letterman tried to defuse the moment with a joke: “You know what they say about guys with short ties.” But the unease lingered.

Despite these uncomfortable moments, Aniston handled them with admirable calm. She maintained her professionalism, returned to the show again two years later, and kept her sense of humor intact.

A Shift in Tone
By 2008, when Aniston returned to The Late Show, things had changed — at least slightly. Dressed in a stylish pink dress, she brought Letterman a lighthearted gift: a Brooks Brothers tie, the same one she wore (and nothing else) on the cover of GQ magazine. “An early Christmas present,” she smiled. Letterman immediately swapped his own tie for the one she brought, and the moment was far more playful than awkward.

A Different Perspective Today
Aniston has never publicly commented on these exchanges, but watching them now through a modern lens makes one thing clear: what was once brushed off as “late-night humor” now feels invasive and disrespectful. Her composure in those moments is admirable — but the need for boundaries and mutual respect in media has never been more apparent.

Looking Back With Clarity

While Aniston navigated those uncomfortable interviews with grace, they now serve as a reminder of how public figures — particularly women — have often had to tolerate inappropriate behavior for the sake of appearances. What was once normalized is now being reexamined, and rightfully so. These moments don’t just highlight Letterman’s questionable choices — they underline how much society has shifted in its expectations for respectful dialogue and personal boundaries.