David Letterman, once celebrated as the king of late-night television, is now facing renewed scrutiny over how he treated female guests on air. One resurfaced example is Jennifer Aniston’s 2006 appearance on The Late Show, where she was promoting The Break-Up. Instead of discussing her film, Letterman repeatedly focused on her legs and outfit, making comments that shifted the tone from playful to uncomfortable.

As the interview went on, Letterman continued to praise her body and even joked that someone should “record the shot,” pushing the moment further into awkward territory. Aniston laughed politely and tried to steer the conversation back to her work, but the exchange highlighted a power imbalance many viewers now see clearly in hindsight.

He also pressed her about a rumored romance with Vince Vaughn, asking questions she deflected with professionalism. The moment echoed a 1998 appearance in which Letterman unexpectedly grabbed Aniston’s neck and sucked on her hair—an invasive act that later went viral and is now widely condemned.

These clips have resurfaced online, sparking conversation about how women were once treated on late-night television and how cultural standards have changed. What was once brushed off as humor is now recognized as inappropriate, making Aniston’s calm, composed responses stand out even more today.