The man was Frank DiLeo — a short, cigar-smoking music executive who became Michael Jackson’s manager in 1984, right as Thriller turned him into the biggest star on the planet. He ran the Bad tour, the Moonwalker film and several of the videos.
Michael called him “Uncle Tookie.”
And by every account, managing the most famous entertainer alive also meant being the target of his pranks — relentlessly.
The story Michael’s own official account has shared is almost too good. Michael would take $100 bills from DiLeo’s hands and throw them down to the people below, while DiLeo stood there watching his own cash float away, and Michael enjoyed every second.
Michael Jackson punked Russell Crowe and Frank DiLeo
But money was not his most effective weapon. That was Muscles.
Muscles was Michael’s eight-foot boa constrictor, and Frank DiLeo was reportedly seriously frightened of snakes. Michael knew this. So he used it.
Accounts of the friendship describe one prank going so far that the terrified manager reached for a security guard’s gun. Michael, naturally, found it hilarious.
Why Frank DiLeo Was So Important To Michael Jackson
What makes the pranks worth telling is that the relationship underneath them was real and it lasted. DiLeo was not a hired hand Michael tolerated. He was one of the very few people Michael genuinely trusted with his career — which is exactly why Michael felt free to torture him.
And the proof is in how it ended. DiLeo’s management ended in 1989, and the two men went their separate ways for years. Then, in 2009, as Michael prepared for the This Is It concerts in London, he brought Frank DiLeo back.
Twenty-five years after he first hired him, with everything on the line, Michael went and got Uncle Tookie.
DiLeo was there until the end. He died in 2011.