The 'If It Makes You Happy' hitmaker was waiting tables in Los Angeles, in between work as a singer for other artists in a studio, and one day she overheard the King of Pop was holding auditions for the role, and ended up getting herself a try-out by crashing the trials.
Looking back on the wild time in an interview with InStyle, she recalled: ''My big break came about eight months after I moved to Los Angeles. I was recording a session singing backup, and I overheard some people talking about auditioning for Michael Jackson's tour, so I found out where it was, crashed the audition, and wound up landing the job as one of his backup singers. It was absolutely crazy and one of those meant-to-be moments.''
Sheryl - who went on to forge her own incredible music career, selling more than 50 million albums worldwide, after performing as a backing singer for the likes of Tina Turner, Don Henley, Stevie Nicks and Bob Dylan as well as the King of Pop - ended up touring with the late music icon on his 'Bad World Tour' between 1987 and 1989, and regularly performed with Jackson on 'I Just Can't Stop Loving You'.
The 56-year-old Grammy-winner had been living scrupulously until she landed the big break, but thanks to the 'Thriller' hitmaker she was able to afford more luxuries.
She added: ''I was renting a one-room apartment in LA., waiting tables at a jazz club, and living check to check.
''Finally I could afford things! At the time, my car had a boot on it because I illegally parked it so many times and I couldn't pay the tickets. When I landed that gig, I finally could afford to get the boot taken off of my car.''
Sheryl hasn't forgotten what it was like to have little in the bank, and teaches her adopted sons - Levi, eight, and 11-year-old Wyatt - that they have to work hard to have nice things.
She said: ''I wasn't a kid who got everything I wanted. I'm trying to raise my boys that way so that they understand that everything has worth and there are certain things you have to work for. I think it's valuable in this day and age because children are growing up with more at their disposal.''
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