David Letterman was formerly regarded as the monarch of late-night television, recognized for his keen humor and talent for captivating audiences.

In the current cultural context, several of his previous interviews have not stood the test of time. Certain discussions, especially those involving female guests, are now being scrutinized more closely.

A notable instance that has come to light pertains to Jennifer Aniston, whose 2006 appearance on The Late Show with David Letterman caused discomfort among numerous viewers.

During that period, Aniston was actively promoting The Break-Up, a romantic comedy in which she starred with Vince Vaughn, who was also a co-writer and producer of the film.

What began as a standard late-night interview unexpectedly shifted to an uncomfortable situation when Letterman became preoccupied with Aniston’s legs.