At the time, they were two of the biggest names in music and film but one was an adult and the other was a child star, barley 10 when he made his big break. For most outsiders, it was seemed an odd relationship.
Yet despite the age gap, Michael Jackson and Macaulay Culkin were best of friends, and the Home Alone actor's famed sleepovers at the singer's Neverland Ranch are still talked about today.
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Not much is known about what exactly happened during his visits to the Billie Jean singer's home but in a recent interview for the Inside You podcast, Culkin opened up about the the speculation surrounding his 'weird' relationship with Jacko.
The 38-year-old said: "He reached out to me because a lot of things were happening, big and fast with me and I think he identified with that. At the end of the day, it's almost easy to say it was weird or whatever, but it wasn't because it made sense.
"We were friends. It's one of my friendships that people question only because of the fact that he was the most famous person in the world."
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He added: "I was a peerless person, nobody at my catholic school even had this much idea of what I was going through and he was the person who had been through the exact same thing and wanted to make sure I wasn't alone."
The Richie Rich actor said he wasn't interested in fame and Jackson liked the fact that he treated him like a normal person and Culkin says the two of them would even play pranks on people.
He added: "He was fucking awesome. He was funny, he was sweet - people didn't know how funny he was. He liked prank calling people, because obviously he was good with his voice. He was hilarious, he was charming, and silly.
"Here's the thing, I really didn't give a shit about famous people, I was thoroughly unimpressed by them, so when I first met him I was like 'oh, cool you're that guy'.
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"I think that's one of the reasons that we also go along, because everyone was always thoroughly impressed by him, so the fact there was someone who treated him like a normal person, it was just that simple.
"For me, it's so normal and mundane. I know it's a big deal to everyone else, but to me, it was a normal friendship."
The two stars became so close that Jackson eventually asked Culkin to be godfather to his three children.
Topics: UK News, TV and Film, Interesting, Michael Jackson, US Entertainment, macaulay culkin