David Letterman was once revered as a late-night icon, but some of his past interviews haven’t aged well — especially one with Jennifer Aniston.
In a 2006 appearance on The Late Show to promote The Break-Up, Aniston endured a cringeworthy interview where Letterman repeatedly fixated on her legs. Dressed in a black blouse and shorts, she became the subject of his ongoing comments, including, “You can only wear that if you have lovely, well-shaped, muscular, lengthy legs.” Aniston, clearly uncomfortable, laughed it off, blaming the heat.
Letterman wouldn’t let it go, circling back with more remarks like, “I can’t get over your legs,” and “I hope to God somebody is TiVoing this.” He also questioned her about her rumored relationship with co-star Vince Vaughn and her nude scene in the film, making the exchange even more awkward.
This wasn’t the first time Letterman made Aniston uncomfortable — a 1998 interview saw him sucking on her hair, a moment that resurfaced years later and drew criticism online.
Despite these unsettling moments, Aniston always handled herself with grace. She returned to The Late Show in 2008 to promote Marley & Me, wearing a pink dress and gifting Letterman the Brooks Brothers tie she wore on the cover of GQ. The playful moment lightened the mood, but for many, the earlier interviews remain hard to watch today.