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.
