David Letterman was once considered one of late-night television’s biggest stars, but some of his past interviews are now being viewed very differently. Among the most discussed is Jennifer Aniston’s 2006 appearance on *The Late Show*, where repeated comments about her appearance left many viewers uncomfortable.

While promoting *The Break-Up*, Aniston arrived dressed in a black blouse and shorts, but the conversation quickly shifted away from her film. Letterman praised her outfit, saying, “**That’s a tremendous outfit… because you have tremendous legs,**” before returning to the topic several more times. He later admitted, “**I can’t get over your legs,**” making the exchange increasingly awkward as Aniston smiled politely and tried to move the interview forward.

The interview became even more uncomfortable when Letterman questioned her about rumors involving co-star Vince Vaughn and asked whether he wanted her to appear naked in the movie. After a brief pause, Aniston avoided the question by responding that he should have asked Vaughn instead, keeping her composure despite the unexpected line of questioning.

The resurfaced clip has also reminded viewers of an earlier 1998 interview in which Letterman unexpectedly grabbed Aniston’s neck and sucked on a strand of her hair, a moment that has since been widely criticized for crossing personal boundaries. The incident, once brushed aside by many, is now often cited as an example of behavior that would be unacceptable by today’s standards.

As these interviews continue circulating online, they have sparked renewed debate about the treatment of women on late-night television and how public attitudes have changed over time. Although Aniston remained calm and professional during each appearance, many now see the encounters as reminders that behavior once dismissed as entertainment is increasingly recognized as inappropriate and disrespectful.