Michael Jackson Used His “Sexiest Diana Ross Voice” To Play Mischievous Pranks on His Crew on Tour

As thrilling as going on tour and performing all over the country can be, there is also plenty of monotonous downtime, during which the musicians and crew members must find ways to entertain themselves until the next show. For Michael Jackson, he usually filled up this downtime with pranks that ranged from mischievous to terrifying, with plenty of jokes falling somewhere in between. Some of his friends would later recall Jackson utilized his natural talents to make his pranks more believable—namely, his ability to don an ultra-feminine falsetto voice.

Jackson’s precise control over his voice is what helped him become the international superstar that he was, and apparently, it also made him a master prank caller. In Michael Jackson: Unauthorized, biographer Christopher Andersen recounted Jackson using his “sexiest Diana Ross voice” to prank call the musicians on his tour. He would call them and say, “I noticed you with the band tonight, and I thought you were very cute. I would like to meet you.”

The singer would then arrange a meet-up spot somewhere within eyesight of his hotel room. He would then use a pair of binoculars to watch the hopeful musician wait fruitlessly for the woman who would never arrive.

Michael Jackson Had No Small Shortage of Pranks to Play

One of the musicians whom Michael Jackson pranked with his falsetto voice told Christopher Anderson, “So, there you are, standing right out in the open, waiting for this beautiful girl to come along, and Michael is up in his room, laughing his sides off. Later, he will get all the guys to his room, and everyone listens to your conversation with this ‘girl’ on tape, and there sits Michael with this big grin on his face.”

In addition to prank calling (and recording) his bandmates, the “Thriller” singer often pointed his hijinx toward his long-time manager, Frank “Uncle Tookie’ DiLeo. DiLeo found himself on the receiving end of many gaffs, including the multiple times Jackson used to steal hundred-dollar bills from DiLeo’s wallet and toss them into the audience during a show. Another time, Jackson brought an eight-foot-long boa constrictor to DiLeo, who had a phobia of snakes. “Terrified, DiLeo grabbed a security guard’s gun and threatened to shoot it,” Andersen wrote. “Uncle Tookie had to be restrained. Michael laughed.”

Hotel employees who worked during Jackson’s stays mid-tour also reported the pop star tossing water balloons from his balconies and starting food fights in his hotel room. In hindsight, being stood up by a make-believe date seems like the least messy—and horrifying—prank that Jackson pulled. Of course, that’s not to say his friends weren’t walking away with bruised egos. But at least it wasn’t a pie to the face or a snake around the neck?

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