David Letterman was once revered as a late-night icon, but some of his past interviews haven\u2019t aged well \u2014 especially one with Jennifer Aniston.<\/p>\n
In a 2006 appearance on The Late Show<\/em> to promote The Break-Up<\/em>, 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, \u201cYou can only wear that if you have lovely, well-shaped, muscular, lengthy legs.\u201d Aniston, clearly uncomfortable, laughed it off, blaming the heat.<\/p>\n Letterman wouldn\u2019t let it go, circling back with more remarks like, \u201cI can\u2019t get over your legs,\u201d and \u201cI hope to God somebody is TiVoing this.\u201d 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.<\/p>\n This wasn\u2019t the first time Letterman made Aniston uncomfortable \u2014 a 1998 interview saw him sucking on her hair, a moment that resurfaced years later and drew criticism online.<\/p>\n Despite these unsettling moments, Aniston always handled herself with grace. She returned to The Late Show<\/em> in 2008 to promote Marley & Me<\/em>, wearing a pink dress and gifting Letterman the Brooks Brothers tie she wore on the cover of GQ<\/em>. The playful moment lightened the mood, but for many, the earlier interviews remain hard to watch today.<\/p>\n