The 1980s were a golden age for pop music, a vibrant decade that saw the emergence of two unparalleled forces who would forever reshape the global soundscape: Michael Jackson and Prince. Their names are inextricably linked, not just by their monumental impact on music, but by a rivalry that, while often framed as a simple competition for chart dominance, was in reality a deeply personal, complex, and at times, intensely hostile relationship. They were the yin and yang of pop, two artists who, despite their stark stylistic differences, shared an uncanny number of parallels and an equally potent ambition that fueled a legendary, decades-long feud.

Born months apart in 1958, both artists hailed from tough Midwest cities and were raised under the strict discipline of their fathers. Both were musical chameleons, embracing fusion and surrounding themselves with diverse collaborators. They fearlessly challenged societal norms, playing liberally with notions of race, gender, and sexuality, all while idolizing the likes of Sly Stone, Stevie Wonder, and James Brown. Yet, the public narrative often painted them as polar opposites: Jackson, the innocent “manchild” and commercial juggernaut; Prince, the rebellious “sex in transgression” and avant-garde challenger. As The New York Times aptly summarized in 1984, “If Mr. Jackson’s message is all you need is love, Prince’s amounts to all you need is sex.” This simplistic dichotomy, however, masked a more profound and often petty rivalry that extended far beyond record sales.

Their first documented interaction, a seemingly innocuous encounter at a James Brown New Year’s Eve concert in 1983, quickly devolved into a moment of public humiliation that would set the tone for years to come. At this point, Jackson’s Thriller was shattering records, while Prince’s 1999 was receiving critical acclaim. Jackson, invited on stage to sing and dance, electrified the crowd. In a move that hinted at the underlying tension, he then leaned into Brown’s ear, daring him to invite Prince up next. Prince, seizing the opportunity to impress his idol, accepted. But his performance was a disaster. His guitar malfunctioned, and in an ill-fated attempt at showmanship, he tried to swing over the crowd on a prop lamppost that crashed, sending him into the audience. Jackson, never one to miss an opportunity, mercilessly mocked him. According to Quincy Jones, Prince was so “devastated” by the public humiliation that he allegedly tried to run Michael over backstage.

The Grammys mere months later offered no reprieve. Prince left empty-handed while Jackson collected a record-breaking eight awards, further stoking Prince’s desire for similar recognition. The rivalry continued to simmer through the mid-80s. While Prince enjoyed immense critical and commercial success with Purple Rain, beating Thriller for Favorite Pop/Rock Album at the American Music Awards in 1985, another pivotal moment arrived with the recording of the charity single “We Are the World.” Jackson, alongside Lionel Richie and Quincy Jones, spearheaded the project, and a verse was reportedly set aside for a duet between Jackson and Prince. However, Prince was a no-show for the recording, later revealing through his backing guitarist Wendy Melvoin that he “thinks he’s a badass and he wanted to look cool and he felt like the song for ‘We Are the World’ was horrible.”

The following year, Quincy Jones made another attempt to mend fences, hoping to unite the two stars on Jackson’s song “Bad.” Jackson had written the track and envisioned it as a potential duet. The thought of such an epic collaboration—the vocals, the instrumentation, the “faux masculinity from a knife fight dance choreography”—was tantalizing. Prince was reportedly on board until he realized he would have to sing the lyric “Your butt is mine” to Jackson. His refusal was swift and unequivocal: “Don’t worry, this record will be a big hit even if I’m not on it.” The animosity continued to escalate, with Prince reportedly gifting Jackson a box of “voodoo artifacts,” leading Jackson to believe Prince was trying to cast a spell on him. Around this time, Jackson allegedly called Prince “rude and nasty,” lamenting, “It’s not fair. He feels like I’m his opponent. I hope he changes because boy, he’s gonna get hurt. He’s the type that might commit suicide or something.”

As the 80s faded into the 90s, both artists faced significant personal and professional challenges—Jackson with child molestation accusations and Prince with a heated dispute with his record label. Despite these struggles, Jackson reportedly reached out to Prince multiple times for potential collaborations, telling him over the phone, “I think it would be just great.” Yet, a joint effort never materialized.

The rivalry resurfaced dramatically in late 2006, during Prince’s Las Vegas residency. Will.i.am arranged for Jackson to attend a show, and Prince, knowing where Jackson was seated, delivered a strangely “sexually charged moment of dominance.” He emerged into the crowd, swung his hips, and “slapped the base hard in Michael’s face.” It was a deliberate, public act, interpreted by many as payback for the humiliation suffered at the James Brown concert decades earlier. Will.i.am later recounted Jackson’s upset over breakfast the next day: “Why do you think Prince was playing bass in my face? Prince has always been a meanie. He’s just a big meanie. He’s always been not nice to me.”

Despite this, Jackson, ever the hopeful, extended another invitation to Prince the following year, hoping to collaborate on a comeback project. Prince, however, quickly turned it down, leaving Jackson “pretty disappointed.” It was only after Jackson’s untimely death in 2009 that Prince seemed to gain a new perspective on their tumultuous relationship. In a 2010 Ebony interview, Prince spoke about their shared struggles with fame and religion, expressing a wish that he had spoken to Jackson more before he passed away.

The rivalry between Michael Jackson and Prince was a defining narrative of their careers, a clash of titans that captivated the world. While both artists strove for individual recognition, they were often lumped together, their legacies intertwined by comparison. Ultimately, their story serves as a poignant reminder that even at the pinnacle of artistic achievement, human emotions—ambition, insecurity, and envy—can fuel complex and enduring feuds. Yet, it is precisely this tension that contributed to their legendary status, solidifying their positions as two of the most influential and unforgettable figures in music history.