David Letterman was once hailed as a titan of late-night television, famed for his quick humor and effortless ability to engage an audience. But as societal norms evolve, some of his older interviews are being revisited—and not always in a flattering light. Several interactions, especially those involving female celebrities, have sparked renewed scrutiny.

One interview that’s made its way back into public conversation is Jennifer Aniston’s 2006 appearance on The Late Show with David Letterman. What was meant to be a typical promotional stop for her film The Break-Up—which she starred in with co-star and producer Vince Vaughn—quickly veered into uncomfortable territory.

The interview started off as expected, but the tone shifted when Letterman appeared unusually fixated on Aniston’s legs, leading to an awkward moment that left viewers—and Aniston—visibly uneasy.