David Letterman was once hailed as the king of late-night TV, but in today’s cultural climate, many of his past interviews are being reexamined—especially those with female guests. One that continues to resurface is his 2006 interview with Jennifer Aniston, promoting The Break-Up. Dressed in black shorts and a blouse, Aniston was poised and professional. But instead of focusing on her film, Letterman fixated on her appearance. “That’s a tremendous outfit,” he said.
