David Letterman built his career on edgy humor and unpredictable interviews, but many of his old moments now feel uncomfortable—especially Jennifer Aniston’s appearances on The Late Show. During her 2006 visit to promote The Break-Up, Letterman fixated on her legs the moment she sat down, repeatedly commenting on her appearance while Aniston tried, politely, to steer the conversation back to her film. Each attempted redirect was ignored, leaving her smiling through visible discomfort.
The 2006 interview wasn’t even their most unsettling exchange. A clip from 1998 still circulates online, showing Letterman pulling Aniston toward him and putting a strand of her hair into his mouth on live television. She recoiled, stunned, as he handed her a tissue to wipe off the saliva. Every time the clip resurfaces, viewers ask how such behavior was ever considered acceptable.
Despite this, Aniston kept returning to the show, handling every awkward moment with the calm professionalism she’s known for. In hindsight, her interviews with Letterman reflect a broader pattern of how women in Hollywood were treated on late-night TV—expected to laugh off inappropriate behavior with grace.
Today, those clips highlight not her discomfort, but her resilience.