David Letterman built his legacy on edgy humor and unpredictable interviews — but many of his old moments look very different today. One that keeps resurfacing is Jennifer Aniston’s 2006 appearance on The Late Show, an interview that felt awkward then and is downright uncomfortable now.
Aniston came on to promote The Break-Up, dressed casually in shorts because of the heat. Letterman immediately zeroed in on her legs, complimenting them repeatedly and ignoring her attempts to shift the conversation back to the film. She laughed politely, but the unease was obvious.
The interview continued in the same tone. Letterman made remarks about her appearance, stared at her on camera, and pushed into personal territory about Vince Vaughn. Watching it now, the tension in Aniston’s forced smile is unmistakable.
And it wasn’t their first uncomfortable encounter. A viral clip from 1998 shows Letterman pulling Aniston toward him and sucking on a strand of her hair — on live TV. She recoiled, visibly stunned, but still tried to stay composed.
Despite everything, Aniston returned to the show over the years. In 2008 she even brought him a playful gift: a Brooks Brothers tie matching the one from her GQ cover. The exchange was friendlier, but the dynamic was still centered on innuendo and appearance.
Rewatching these interviews today, it’s clear how much the culture has changed. Early-2000s late-night often put actresses in uncomfortable positions — Aniston included. Like many women of that era, she handled inappropriate moments with grace because speaking up wasn’t really an option.
Aniston has never publicly criticized Letterman. But the internet has taken notice, revisiting the clips and questioning why such behavior was considered normal. What stands out most now isn’t Letterman’s jokes — it’s Aniston’s professionalism. She remained poised, calm, and unfailingly gracious, even when the interviews crossed lines.
Her resilience is the part that has aged well. The rest hasn’t.