David Letterman’s question that l
David Letterman’s legacy is being reassessed as past interviews resurface,
including an uncomfortable 2006 exchange with Jennifer Aniston on The Late Show.
While promoting The Break-Up, Aniston found the focus shifted from her film to her appearance.
Letterman told her, “That’s a tremendous outfit… because you have tremendous legs,” later adding, “I can’t get over your legs.”
He even joked that someone should tape the show because of “the shot.”
The interview grew more awkward when he pressed her about rumors involving Vince Vaughn and asked an inappropriate question about appearing naked.
Aniston deflected calmly. Viewers also recall a 1998 interview in which Letterman crossed physical boundaries, a moment now widely criticized.
Clips of these encounters have sparked outrage online, highlighting how behavior once dismissed as
humor is now viewed as inappropriate, reflecting shifting cultural standards around respect and consent.
