David Letterman was once a dominant figure in late-night television, but some of his past interviews are now being viewed more critically. One resurfaced moment involves Jennifer Aniston’s 2006 appearance on The Late Show, where the conversation became uncomfortable due to Letterman’s repeated comments about her legs rather than her work.

Although Aniston handled the situation professionally, laughing it off and redirecting the discussion, the remarks stood out as awkward and inappropriate by today’s standards. The interview also included intrusive questions about her relationship with co-star Vince Vaughn, further adding to the discomfort.

This was not an isolated incident. A 1998 interview, in which Letterman grabbed Aniston and put a strand of her hair in his mouth, has also resurfaced and sparked renewed criticism. While such behavior was once dismissed as late-night humor, it is now widely viewed as invasive.

Though Aniston never publicly addressed these moments, the clips highlight how female celebrities were often subjected to uncomfortable treatment in media interviews. Today, these interviews are seen as examples of how cultural standards have changed—and how certain behaviors have aged poorly.