The nine-time Grammy Award winner, 59, recalled getting her big break in 1987 when she auditioned for Jackson's first solo world tour during an interview with The Independent.
"Naiveté is such a beautiful thing," Crow mused.
"It was incredible in every way, shape, and form for a young person from a really small town to see the world and to work with arguably the greatest pop star," she continued. "But I also got a crash course in the music industry."
Crow recalled tabloid stories that Jackson had fallen in love with his "sexy backing singer" and even offered her $2 million to have his baby. In her memoir audiobook Words + Music, which was published in September, she ventured to guess that the stories were planted by DiLeo, "to make Mike look like he was interested in women."
Crow claimed that it was actually DiLeo who was interested in her, promising to make her a star while subjecting her to sexual harassment. She also alleged that he threatened to end her career if she refused his advances. Crow did just that, before returning to her Los Angeles apartment in 1989, where she experienced a lengthy bout of depression.
"It's really interesting to go back and revisit some of this old stuff and the experiences that went along with it, and then to compare it with where we are now," she said. "To be able to play that stuff about the long bout of sexual harassment I endured during the Michael Jackson tour and to talk about it in the midst of the MeToo movement... it feels like we've come a long way, but it doesn't feel like we're quite there yet."
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The Threads artist made reference to DiLeo in two songs on her 1993 debut album Tuesday Night Music Club, including "What I Can Do for You", which was written from the perspective of an abuser, as well as "The Na-Na Song", a stream-of-consciousness featuring the lyric: "Frank DiLeo's dong / Maybe if I'd have let him I'd have had a hit song."
She said that Words + Music "was the first time I've ever talked about it and it felt really uncomfortable, but it felt, to me, so much more empowering to be able to talk about it and then play the music that was inspired by it."
"Isn't that what music is really for?" Crow added. "To help us work through whatever our experiences are, and hopefully for the collective to find their own situations in your music too?"
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DiLeo worked with several artists over the years, most notably Jackson. He managed the artist in the late '80s and again in 2009, up until Jackson's death that June. DiLeo died in August 2011 of complications following heart surgery. He was 63.
Crow previously commented on sexual assault allegations brought against Jackson over the years when the HBO documentary Leaving Neverland premiered in 2019. "It's like a death in the family, you know? It's sad," she said to The Guardian.
"I think that there were a lot of exceptions made because of the damage that [Jackson] … I mean, he didn't intentionally project it, but it was part of his aura - this almost being untouchable and almost alien-like [figure]," Crow added. "And, yeah, I mean, I'm sad, and I'm mad at a lot of people. I feel like there was just a huge network of people that allowed all that to go on. It's just tragic."