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.
https://www.youtube.com/embed/0kD7EAuHVKY
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.