The Photo Is Not Manipulated, Look Closer And Try Not To Gasp When You See It
David Letterman once reigned as the undisputed king of late‑night TV, celebrated for his razor‑sharp humor and effortless charm. But many of his past interviews haven’t aged gracefully—none more so than his 2006 chat with Jennifer Aniston, then promoting The Break‑Up. What began as a routine promo quickly veered into uncomfortable territory when Letterman fixated on Aniston’s legs.
Seated in a chic black blouse and tailored shorts, Aniston looked every bit the effortless movie star. Yet Letterman couldn’t resist commenting, “That’s a tremendous outfit—and the reason is you’ve got tremendous legs. Well‑shaped, muscular, lengthy legs.” Aniston flashed a polite laugh, explaining she’d chosen shorts simply because it was hot, but Letterman circled back again: “Your legs—you’ve really got something there.” At each turn, his gaze lingered on her thighs rather than her work.
The awkwardness peaked when he quizzed her about rumors surrounding Vince Vaughn—co‑star and co‑writer of the film—asking whether he’d insisted she appear nude onscreen. Aniston deftly deflected, suggesting he should take that question to Vaughn himself. Somehow, though, the conversation always returned to her legs: “I can’t get over your legs,” he confessed, drawing audible gasps. Even his comment about someone TiVoing “this shot” left the audience—and Aniston—visibly unsettled.
