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David Letterman, once hailed as the king of late-night television, is now facing renewed scrutiny over past interviews, particularly those with female guests. One interview that has resurfaced involves Jennifer Aniston’s 2006 appearance on The Late Show while promoting The Break-Up. What started as a promotional segment quickly turned uncomfortable, as Letterman repeatedly commented on Aniston’s legs rather than her work.

Wearing a stylish black blouse and shorts, Aniston became the subject of unwanted focus. Letterman’s remarks—calling her legs “tremendous” and “well-shaped”—left her visibly uneasy. Although she laughed it off, attempting to redirect the conversation, Letterman persisted. He returned to the topic more than once, remarking, “I can’t get over your legs,” and even joked about wanting someone to record the moment at home.

The interview worsened when Letterman pressed Aniston about her rumored romance with co-star Vince Vaughn and questioned if it was Vaughn’s idea for her to appear nude in the film. Aniston, caught off guard, deflected with grace, suggesting Letterman should have asked Vaughn when he was on the show. Despite her efforts to steer the conversation, Letterman kept circling back to her appearance.

This wasn’t the first uncomfortable exchange between the two. In 1998, Letterman shocked viewers by sucking on a strand of Aniston’s hair during an interview, leaving her visibly disturbed. That clip has gone viral multiple times, reigniting criticism of his behavior and the broader treatment of women in media.

Still, Aniston continued to appear on the show. In 2008, she returned with a gift for Letterman—a tie identical to one she wore on GQ’s cover. The exchange was playful, but again included innuendo and audience gasps, reflecting an ongoing pattern.

Viewed today, these interviews highlight a shift in cultural awareness. What was once brushed off as humor now sparks deeper conversations about respect and boundaries for women in entertainment.