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1. Madonna – 1994

During an interview with David Letterman in 1994, pop queen Madonna greeted him and did something that seemed a bit weird. She sneakily shook his hand and passed off a pair of underwear to him. Was the star the actual owner of the clothing item or did she buy them from a random store?

And that is not all. Right at the start of the interview, the singer called the show host “sick”, but in a cheerful way, due to the fact that he was always asking about her intimate life. Now that we know all the facts, we might say that Madonna’s gesture was actually a way to make Letterman stop with those inappropriate questions.

2. Drew Barrymore – 1995

…This one is a bit over the top if you ask us! 

Once again, the “victim” of this next odd behavior is David Letterman. He did an interview with actress Drew Barrymore in 1995 for his show called “The Late Show”, when she suddenly got up from her seat, jumped on the host’s desk, and started dancing provocatively.

And now it’s time for the cherry on top: out of nowhere, she quickly flashed him with her breasts. As the star said, her gesture actually had a meaning behind it: it was Letterman’s birthday and this was her gift for him.

…Did you know about the weird present Barrymore gave to Letterman?

3. Michael Jackson – 2003

We can’t tell for sure if the talented singer and performer Michael Jackson was actually guilty of the child abuse allegations filed against him, but we can say that he did say a few things many people found disturbing, given the circumstances.

When he talked about his own kids, the star said that he doesn’t mind when their friends come over and sleep in his bed, because everything is just “very charming”. There are quite a few documentaries about Michael Jackson, whether we’re talking about his career, personal life, or the accusation brought against him.

Some people say that he was guilty, some say that those victims were not actually victims and all they ever wanted was money, but one thing is for sure: only he knew what has actually happened behind the closed doors of Neverland.

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