I Showed Up to Work Soaked After Saving a Drowning Puppy – My Boss Told Me to Get Lost,

David Letterman built his career on sharp, unpredictable comedy, but some of his interviews haven’t aged well. Jennifer Aniston’s 2006 appearance on The Late Show is a prime example. Promoting The Break-Up, she was polite and smiling, but Letterman repeatedly commented on her legs and made personal jokes that left her visibly uncomfortable.

This wasn’t isolated—clips from 1998 show him pulling her hair into his mouth, shocking viewers even today. Despite the awkwardness, Aniston handled it with professionalism, redirecting conversations with humor and composure, never publicly criticizing him. Later appearances, like 2008’s Marley & Me interview, remained light but still included remarks on her appearance.

Seen today, these moments reflect a broader pattern in early-2000s media, where actresses were often placed in invasive situations on live TV. What stands out is Aniston’s grace—her dignity and resilience have aged far better than the clips themselves, highlighting how much both she and media culture have evolved.