David Letterman’s question that left Jennifer Aniston very uncomfortable

David Letterman, once a dominant figure in late-night television, is facing renewed criticism for his treatment of female guests during past interviews. One such instance gaining attention again is Jennifer Aniston’s 2006 appearance on The Late Show.

During what was meant to be a promotional interview for The Break-Up, Letterman repeatedly fixated on Aniston’s legs instead of discussing her film. Dressed in a black blouse and shorts, she became the focus of unwanted remarks.

Letterman described her legs as “tremendous” and “well-shaped,” making Aniston visibly uncomfortable. Though she tried to shift the conversation, he continued to bring it up, even joking about someone recording the moment at home.

The conversation became more awkward when Letterman questioned her about rumored relationship with co-star Vince Vaughn and if he influenced her nude scene in the movie. Aniston deflected with poise, suggesting he ask Vaughn directly.

Their awkward interactions weren’t new. In a 1998 interview, Letterman shocked audiences by putting a strand of Aniston’s hair in his mouth, visibly disturbing her. That clip has resurfaced repeatedly, reigniting discussions on inappropriate conduct.

Despite these uncomfortable moments, Aniston returned to the show in 2008 and gifted Letterman a tie similar to one she wore on a GQ cover. The segment, while playful, once again included innuendo and audience reactions.

Today, these interviews are being reexamined through a modern lens, highlighting how public expectations around boundaries, humor, and respect toward women in media have evolved significantly.