David Letterman, once revered as the king of late-night TV, is now facing scrutiny for past interviews that haven’t aged well—particularly those with female guests. One resurfaced moment involves Jennifer Aniston’s 2006 Late Show appearance, where she was promoting The Break-Up. Instead of focusing on her film, Letterman repeatedly commented on her legs, leaving Aniston visibly uncomfortable.

The situation worsened as he circled back multiple times to her appearance and even questioned her about posing nude in the film, asking if it was Vince Vaughn’s idea. His fixation on her body and persistent personal questions shifted the tone from professional to invasive. Aniston, ever composed, deflected with grace, but the tension was obvious.

This wasn’t the only troubling moment. In a 1998 interview, Letterman grabbed Aniston’s neck and sucked on a strand of her hair—a moment that still goes viral today. Despite her visible discomfort, he handed her a tissue, expecting her to clean up. These clips now spark outrage and highlight how inappropriate late-night “humor” could be.

Though Aniston continued appearing on the show, her interactions with Letterman underscore the broader issue of how female celebrities were often treated in media. As public awareness grows, these moments are being reevaluated, prompting important conversations about respect and professionalism in entertainment.