David Letterman, once hailed as the king of late-night TV, is now facing scrutiny for interviews that haven’t aged well—especially those with female guests. One such case involves Jennifer Aniston’s 2006 appearance on *The Late Show*, where the focus drifted uncomfortably from her film *The Break-Up* to her physical appearance.

“That’s a tremendous outfit,” Letterman told her. “And the reason that’s a tremendous outfit is because you have tremendous legs.” Aniston, caught off guard, laughed it off, citing warm weather as the reason for her outfit. But Letterman didn’t drop the topic, later adding, “I can’t get over your legs… You got something there.”

Things grew more awkward when he questioned her about a nude scene and her rumored relationship with Vince Vaughn. Aniston deflected, saying, “You should’ve asked Vince when he was here.”

This wasn’t their first uncomfortable exchange. In 1998, Letterman bizarrely sucked on a strand of her hair, handing her a tissue afterward. A resurfaced clip of the moment went viral in 2021 with the caption: “Since we’re talking about David Letterman being awful…”
Aniston continued appearing on the show with grace, but looking back, many now see these interviews as unsettling reminders of a different era in media.