Conversations about evolving cultural norms often arise when old television clips resurface, and a series of David Letterman interviews with Jennifer Aniston has once again sparked reflection. While Letterman was long celebrated for his wit and late-night charm, some moments from past episodes feel markedly out of step with today’s expectations. One frequently discussed instance comes from a 2006 appearance in which Aniston visited The Late Show to promote her film The Break-Up. Rather than centering the discussion on her work, Letterman repeatedly fixated on her appearance, specifically her legs, creating a noticeably uncomfortable exchange.

As the interview unfolded, Letterman continued returning to the same topic, telling Aniston he couldn’t “get over” her legs and even joking that someone at home should be recording the segment because he couldn’t stop watching a particular camera angle. The comments shifted the focus away from her professional accomplishments, leaving Aniston to smile politely while attempting to redirect the conversation. The host also touched on rumors about her relationship with co-star Vince Vaughn and questioned whether a nude scene was his idea—topics she gently but firmly deflected in an effort to reestablish control of the dialogue.

This wasn’t the first time their on-air interactions raised eyebrows. A 1998 clip, now widely recirculated online, shows Letterman unexpectedly grabbing a lock of Aniston’s hair during an interview—an action that, even in the moment, appeared startling but proceeded without interruption. Modern viewers often express disbelief at how casually the incident unfolded and how normalized such behavior once was in mainstream entertainment, despite Aniston maintaining her composure throughout.

Revisiting moments like these offers a clear look at how expectations around respect, boundaries, and professionalism in media settings have evolved. What may have once been dismissed as comedy is now recognized as behavior that undermines a guest’s comfort and agency. These resurfaced interviews highlight the progress made in advocating for more thoughtful, equitable treatment of women in the public eye—and remind us of the ongoing responsibility to create environments where every guest feels respected and celebrated for their work.