The interview continued to drift into personal territory. When the topic of Vince Vaughn came up, Letterman joked about whether Vaughn encouraged her to appear nude in the film, catching her off guard. She deflected carefully, trying to steer the conversation back to safer ground. Later, Letterman commented on a camera shot he “couldn’t stop looking at,” leaving viewers to interpret the moment on their own. Aniston kept her composure, but it was difficult to watch even then.
And this wasn’t the only uncomfortable exchange between them. A 1998 clip frequently goes viral because of a particularly strange moment: Letterman pulled Aniston toward him, took a strand of her hair, and put it in his mouth. Aniston looked shocked and uneasy, and the moment still sparks disbelief whenever it resurfaces online.
Social media has repeatedly brought these clips back into the spotlight. One viral tweet in 2021 questioned how such moments were ever considered humorous. Viewed today, the exchanges feel less like light late-night banter and more like examples of how women in Hollywood were often placed in uncomfortable situations on national television.
