David Letterman was once hailed as the king of late-night TV, but in today’s cultural climate, many of his past interviews are being reexamined—especially those with female guests. One that continues to resurface is his 2006 interview with Jennifer Aniston, promoting The Break-Up. Dressed in black shorts and a blouse, Aniston was poised and professional. But instead of focusing on her film, Letterman fixated on her appearance. “That’s a tremendous outfit,” he said.

“You can only wear that if you have lovely, well-shaped, muscular, lengthy legs.” Aniston laughed awkwardly, trying to move on, but Letterman continued, commenting again on her legs and even saying, “I hope somebody is TiVoing this because I can’t stop looking at this shot.” The exchange was uncomfortable then—and cringeworthy now.

It wasn’t their first awkward moment. In a 1998 interview, Letterman stunned viewers by grabbing Aniston’s neck and sucking on a strand of her hair. She pulled away, clearly unsettled, while he handed her a tissue. The clip resurfaced in 2021, reigniting outrage and disbelief. Despite such incidents, Aniston continued to appear on The Late Show, always handling the situations with grace.

During a 2008 visit, she gifted Letterman a necktie, leading to more suggestive banter—typical of the era but far less acceptable today. Viewed through a modern lens, these interactions reveal how normalized such moments once were—and how much has changed in how women in Hollywood are treated and respected on-screen.