David Letterman was once celebrated as the king of late-night television, known for his sharp wit and ability to keep audiences entertained. However, in today’s cultural climate, not all of his past interviews have aged well. Some of his exchanges, particularly with female guests, are now being reexamined with a more critical eye. One such moment that has resurfaced involves Jennifer Aniston, whose appearance on The Late Show with David Letterman in 2006 left many viewers uncomfortable.

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.