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The Most Uncomfortable Letterman Interviews Ever

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In many regards, David Letterman is the perfect antidote to the airless celebrity interview.

During his long, legendary tenure as a late-night talk show host, he earned a reputation for keeping guests on their toes and and cracking plenty of jokes at their expense. Of course, Letterman has also fallen victim to plenty of guests who went out of their way to be openly confrontational, provocative, and gleefully obnoxious. Here’s a closer look at some of David Letterman’s most uncomfortable interviews…

​Madonna | 0:31
Justin Bieber | 1:33
​Michael Richards | 2:20
Crispin Glover | 3:09
​Andy Kaufman | 4:30
Joaquin Phoenix | 5:22

How did Lindsay Lohan react to the questions about her rehab stints and legal problems during her interview with Letterman?

The late-night talk show “Late Show with David Letterman” was renowned for its edgy and unpredictable interviews. Over the years, David Letterman hosted some of the most high-profile celebrities, politicians, and athletes, pushing them outside their comfort zones.

However, some interviews did not go as planned, and some guests ended up feeling uncomfortable and even offended. Here are some of the most awkward Letterman interviews ever.

In 1995, actress Farrah Fawcett appeared on the show to promote her Playboy pictorial. However, things turned sour when Letterman showed footage of her botched appearance at a Lakers game, where she had trouble singing the national anthem. Fawcett got visibly upset and refused to talk to Letterman, and the interview ended abruptly.

In 1997, actress Drew Barrymore appeared on the show to promote her new movie, “Boys on the Side.” However, Letterman, who had interviewed Barrymore since she was a child star, brought up her troubled teenage years and substance abuse issues. Barrymore looked uncomfortable and asked Letterman if they could talk about something else.

In 2009, actor Joaquin Phoenix made a bizarre appearance on the show, claiming he was retiring from acting to focus on his rap career. Phoenix looked disheveled and unresponsive, leading many to speculate that he was either high or playing a prank. Letterman seemed amused but also confused, and the interview ended on an ambiguous note.

In 2013, actress Lindsay Lohan appeared on the show to promote her new movie, “The Canyons.” However, Letterman grilled her about her rehab stints and legal problems, making her visibly uncomfortable. Lohan tried to deflect the questions with humor but seemed relieved when the interview ended.

These are just some examples of the most uncomfortable Letterman interviews ever, but there were plenty more. While some might argue that Letterman pushed the envelope too far, others say that he was just doing his job as a provocative and unpredictable interviewer. Either way, these interviews are a reminder that even the most famous and accomplished people can feel vulnerable and exposed when facing the scrutiny of the public eye.