David Letterman was once the undisputed king of late-night television—a master of sarcasm, quick wit, and awkward charm who turned awkward silences into viral gold long before that term even existed. But with the passage of time and a culture now more attuned to respect and boundaries, many of his old interviews are being rewatched with a different lens. And few moments exemplify that shift more than his uncomfortable 2006 exchange with actress Jennifer Aniston.

At the time, Aniston was promoting The Break-Up, a romantic comedy she co-starred in with Vince Vaughn. It should have been a straightforward press tour stop. Instead, it became an example of how even Hollywood’s brightest stars often had to endure inappropriate attention just to promote their work. From the very beginning of the segment, it was clear the focus wouldn’t be on the film.

Jennifer, dressed tastefully in a black blouse and elegant shorts, took her seat across from Letterman. Before a single line about the movie could be discussed, Letterman zeroed in on her outfit—not to praise her fashion sense, but to objectify her appearance. “That’s a tremendous outfit,” he said, then added, “because you have tremendous legs. Fantastic legs. You can only wear that if you have lovely, well-shaped, muscular, lengthy legs.”

Aniston, ever the professional, responded with grace, brushing it off with a laugh and noting the warm weather. But the discomfort on her face was obvious. Rather than moving on, Letterman circled back again, saying, “Your legs, you’ve got something there.” What should have been a routine interview became increasingly awkward, each compliment a reminder that this wasn’t really about her film or talent at all—it was about how she looked.

Things only got more uncomfortable when Letterman veered into questions about Aniston’s rumored relationship with Vince Vaughn. “Was it his idea for you to be naked in the movie?” he asked, referring to a scene in The Break-Up. Caught off guard, Aniston managed to deflect, suggesting that he should’ve asked Vince when he was on the show. But the tone had been set: a lighthearted promo had turned into a deeply awkward encounter.

Later in the same interview, while she spoke about her co-star, Letterman once again fixated on her legs. “I can’t get over your legs, I’m telling you. You got something there.” Then came a particularly bizarre comment: “I hope to God somebody at the house is TiVoing this because I can’t stop looking at this shot.” It wasn’t clear what he was referencing, but the implication was enough—and Aniston’s expression confirmed that the moment had taken a turn for the worse.

Unfortunately, this wasn’t the only time Letterman had made Aniston visibly uncomfortable. A previous interview from 1998 resurfaced years later and went viral for all the wrong reasons. In that encounter, Letterman inexplicably leaned over, grabbed Aniston’s neck, and sucked on a strand of her hair. The moment left viewers stunned and Aniston clearly unsettled. She recoiled in awkward disbelief, using the tissue Letterman handed her to wipe her hair, trying to make light of a gesture that felt deeply invasive.

The clip made the rounds again in 2021, reigniting public discussion about the ways women—especially actresses—have long been subjected to behavior that was once dismissed as “entertainment.” One viral tweet put it plainly: “Since we’re talking about David Letterman being awful… is anyone ever going to address this?”