At the time, Aniston was promoting The Break-Up, the romantic comedy she starred in alongside Vince Vaughn, who also co-wrote and produced the film. What started as a routine late-night interview quickly took an awkward turn when Letterman became fixated on Aniston’s legs.

Dressed in a black button-down blouse paired with stylish black shorts, Aniston looked effortlessly chic. However, instead of focusing on her work, Letterman’s attention was elsewhere.

“That’s a tremendous outfit,” he commented, before quickly adding, “and the reason that’s a tremendous outfit is because you have tremendous legs. Fantastic legs. You can only wear that if you have lovely, well-shaped, muscular, lengthy legs.”

The remark left Aniston visibly taken aback. Ever the professional, she laughed it off, brushing it aside by casually explaining that she