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David Letterman Made This A-List Guest Visibly Uncomfortable By Pressuring Her To Kiss A Stranger On Camera


  • David Letterman made Madonna visibly uncomfortable during their 1994 interview, pressuring her to kiss a stranger in the audience.
  • Madonna’s body language showed her discomfort.
  • Letterman acknowledged that he was making Madonna uncomfortable.

During David Letterman’s tenure as one of the ’90s’ best talk show hosts, he created a slew of memorable moments. Unfortunately for the celebrities involved, some of Letterman’s most talked about moments involved him making his guests so upset they walked out on him.

In Letterman’s case, angering his guests helped make him so successful that he became rich and can afford an incredible lifestyle. On the other hand, some of Letterman’s guests, including a legendary pop star he tried to make kiss an audience member, seemed very upset with the host.

David Letterman’s Madonna Interview Was One Of The Worst Of His Career

In 2022, David Letterman’s YouTube channel uploaded a 1994 interview the talk show host conducted with Madonna. The interview is so memorably hard to watch that Letterman’s own channel labeled the interview “infamous”. One of the most amazing parts of the interview came when Letterman tried to get Madonna to kiss someone from his audience.

Via: Instar

As the video of Letterman’s interview of Madonna begins, the crowd can be heard joyously applauding Madonna. Once the applause came to an end, the first thing that Letterman did was to try to get her to kiss a man in the audience.

“Oh come on. Let’s go kiss a guy in the audience. Why don’t you go kiss the guy in the audience?”

In response to Letterman’s strange request, Madonna could be seen with an awkward smile on her face. Madonna then asked the host why he was obsessed with who she had intimate encounters with.


Years Before Chris Rock Admitted To Cheating On His Wife, He Mercilessly Mocked David Letterman’s Affairs To His Face

When David Letterman admitted he’d engaged in many affairs, Chris Rock came on his show to mercilessly mock him to his face.

Given Madonna’s pointed question, it already seemed like she was uncomfortable with what was going on. However, after Letterman cracked a joke at his own expense, he continued with his attempt to get Madonna to kiss someone in his audience.

Which celebrity guests did David Letterman make visibly uncomfortable, according to Showbiz Cheatsheet?

  • Jennifer Aniston
  • Jennifer Lopez
  • Madonna
  • Janet Jackson
  • Jessica Alba

“Go kiss the guy in the audience. It would knock him out. Look at that guy. Just like, on the forehead, on the forehead.”

David Letterman Interview
Via: Deposit/Commons Licences 

On top of having Letterman trying to get her to kiss a random man she knew nothing about, Madonna had something else to contend with. Every time Letterman urged Madonna to kiss the stranger, the talk show host’s audience went crazy with excitement.

What talk shows is David Letterman best known for according to Britannica?

Talk Show:

Premiered In:

Ended In:

Late Night with David Letterman



Late Show with David Letterman



My Next Guest Needs No Introduction with David Letterman



If that wasn’t enough, Letterman’s producers also turned the camera on the audience member who wanted to kiss the pop star. That audience member even went so far as to hold his hands together to mime begging Madonna to kiss him.

Throughout Madonna’s career, she has almost always come across as being very open with the public. With that in mind, it is incredible to look at Madonna’s body language as she was being pressured to kiss a stranger.


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Conan O’Brien is celebrated as one of the best talk show hosts but David Letterman once though he wouldn’t succeed at all.

As David Letterman and his audience tried to get Madonna to kiss an audience member, she could be seen sitting in a defensive posture. On top of that, Madonna kept her arms crossed across her chest in a position that indicated how uncomfortable she was.

While sporting an insincere-looking smile and uncomfortably laughing, Madonna tried in vain to argue she couldn’t kiss the stranger.

“I can’t. He’s not tall enough.”

David Letterman from his talk show
Via: CBS

Of course, no one can know what is going on in someone else’s mind at any given moment. As a result, observers could choose to believe that Letterman didn’t realize how uncomfortable he was making Madonna even though it seemed obvious to viewers.

When it comes to this infamous moment, however, there is no denying that Letterman realized he was making Madonna uncomfortable. The reason for that is that just before Madonna finally got the host to change the subject, Letterman said something extremely telling. Letterman outright said that most guests would buckle just to avoid the pressure he was putting on Madonna at that moment.

“A lot of people would cave into the pressure and say, ‘Oh, alright.’ They’d go out and kiss him and get it over with.”

Why David Letterman’s Infamous Madonna Interview Went Off The Rails

Immediately after David Letterman commented on trying to pressure Madonna to kiss a stranger, she turned the tables on him. Madonna did this by outright calling Letterman sick as she labeled him with profanity.


Fans Went Wild When David Letterman Publicly Slammed Jay Leno During His Late Night Wars With Conan O’Brien

David Letterman delighted in calling Jay Leno out amid his feud with Conan O’Brien over The Tonight Show.

As the rest of Madonna’s memorable appearance on Letterman’s show played out, things only got worse. At various points, the pop star refused to leave the stage, she insulted Letterman repeatedly, she swore many times, and she smoked a cigar. Those are just a handful of the many ways that the interview got weird.

Many years later, in 2015, Madonna explained her strange Letterman interview while talking to Howard Stern. According to Madonna, she was in a strange mood that day because Tupac Shakur got into her head.

Madonna and Tupac
The Things

“I was in a weird mood that day. I was dating Tupac Shakur at the time, and he had got me all riled up about life in general. So when I went on the show I was feeling very gangster.”

In 2019,
David Letterman apologized for his past sexist behavior
. According to a comedy writer named Nell Scovell who previously worked with Letterman, the host reached out to meet with her. Letterman then apologized for how he treated her and other women who worked for him.

Of course, Madonna linking Tupac Shakur to her past behavior was noteworthy enough to garner lots of headlines. However, it seems all but certain Letterman making Madonna so uncomfortable as their interview began played a large role in how weird things got.

Source: NewsFinale

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