David Letterman was once universally considered one of late-night television’s biggest stars, but some past interviews are now viewed differently.

Among the most discussed celebrity segments online is Jennifer Aniston’s memorable 2006 promotional appearance on The Late Show.

During the broadcast, the host’s repeated personal comments about her physical appearance left many studio viewers feeling incredibly uncomfortable.

While actively promoting her new film The Break-Up, Aniston arrived on set dressed in a stylish black blouse and matching shorts.

However, the televised conversation quickly shifted away from her acting project and directly toward her physical body parts instead.

Letterman praised her outfit on air, loudly stating that she had tremendous legs before returning to the sensitive topic several more times.

He later admitted on camera that he simply could not get over her legs, making the entire media exchange increasingly awkward on set.

Aniston smiled politely through the pressure and tried her best to move the professional interview forward to the movie details.

The interview became even more uncomfortable when Letterman questioned her about intimate rumors involving her co-star Vince Vaughn.

He directly asked the actress whether Vaughn had explicitly requested that she appear completely naked in the film’s final cut.

After a brief, tense pause on the live set, Aniston skillfully avoided the intrusive question by responding that he should have asked Vaughn instead. While she managed to keep her composure despite the unexpected line of questioning, the studio producers noticed that Letterman was getting ready to reference a hidden tape from her past that would shock…