It would have been the showdown of the decade, an epic song-video exchange between the two towering talents of a generation. The Gloved One versus the Purple One. The King of Pop versus His Royal Badness. Michael Jackson versus Prince.
The pop stars met to discuss the proposed standoff in late September, 1986. Earlier that month, Jackson’s groundbreaking 4-D sci-fi film attraction, Captain EO, premiered to packed crowds at Disneyworld and Disneyland. Directed by Francis Ford Coppola (and produced by George Lucas), it demonstrated, among other things, Jackson’s considerable standing in the industry. In the aftermath of Thriller, artists, filmmakers and corporations alike were jumping at the chance to work with him. Everything he touched seemed to turn to gold. After months of working on the set of Captain EO, the artist was now busy recording songs and conceptualizing short films for his highly-anticipated new album, Bad.
Prince, meanwhile, saw the release of his own music film, Under the Cherry Moon (and accompanying soundtrack, Parade), earlier that summer. A stylized, black-and-white romantic dramedy set in the beautiful French Riviera and directed by Prince himself, the film failed to make a splash at the box office (or among most critics). Its artistic ambition, however, was clear and it yielded Prince one of the most successful singles of his career with the funky #1 hit, “Kiss”. Upon his return from France, riding a creative high, Prince went to work on a collection of songs intended as a three-LP album entitled Crystal Ball, which was later consolidated into the critically acclaimed masterpiece, Sign O’ the Times.
In 1986, then, Prince and Michael Jackson were at the top of their respective games, the musical equivalents of Magic and Bird. Both were coming off massive, record-breaking albums in Thriller and Purple Rain. Both had built up legendary mystiques by rarely granting interviews and cultivating eccentric, constantly shifting images. Both kept their audiences guessing. No other ’80s stars — not Madonna, not Bruce Springsteen, not Bono — evoked the same level of fascination from the public.
This public interest, of course, only grew when it came to their cryptic relationship with each other. Throughout the ’80s hundreds of articles ran with sometimes real, but mostly fictional scoops about their rivalry. A National Enquirer story in 1985 claimed Prince was using ESP to drive Jackson’s chimpanzee, Bubbles, crazy.
In most articles comparing the artists, they were depicted as polar opposites: Jackson was the innocent man-child to Prince’s licentious rebel. Jackson was the polished, sophisticated prodigy from Motown, while Prince was the raw, self-taught genius from the streets of Minneapolis. Jackson was the mainstream, commercial juggernaut, while Prince was the alternative, avant-garde challenger. Jackson was magic and wonder; Prince was sex and transgression. It was the 2.0, in many ways, of the rivalry between the charming Beatles and the bad-boy Rolling Stones.
There was obviously some truth to these distinctions. But they were also simplifications. Indeed, part of what made their rivalry so compelling was their similarities.
Both were born the same year, just months apart (Prince on 7 June, Jackson on 29 August), in the summer of 1958. This was only a few years after Rosa Parks refused to give up her seat to a white passenger on a public bus in Montgomery, Alabama, ushering in the Civil Rights Era. When Prince and Jackson were three years old, John F. Kennedy was elected President of the United States. When they were five years old, Martin Luther King, Jr. delivered his “I Have a Dream” speech at the March on Washington. The music of Motown, “the sound of young America”, permeated the airwaves. It was a time of profound changes and possibilities.
Both artists came out of tough midwest cities: Jackson was from Gary, Indiana, a steel town just south of Chicago; Prince was from North Minneapolis, Minnesota, also known for its gritty industrial character. Their first homes — on 2300 Jackson street and 915 Logan Avenue — were modest starter houses out of which their parents dreamed big dreams. Like Gary, North Minneapolis was predominantly African American, but unlike Gary, it was part of what local reporter Neal Karlen called “the whitest metropolitan area in the country.”
Both artists’ roots were in the South. Jackson’s parents were from Arkansas and Alabama; Prince’s were from Louisiana. Two generations removed from slavery and still struggling with the pervasive inequalities of Jim Crow, they migrated north, along with hundreds of thousands of other African Americans, looking for opportunity. Both Prince and Jackson’s fathers were strict disciplinarians who worked long, arduous hours to support their families.
Joseph Jackson was a crane operator at East Chicago’s U.S. Steel company and often worked overtime to put food on the table for his family of 11. Young Michael remembers him coming home after a long day at work exhausted. His only escape was music. Joseph’s rhythm and blues band, The Falcons, practiced in the Jackson family’s small home into the late hours and often played local clubs, hoping to catch their big break. When it became clear to Joseph that this was unlikely to happen his own dreams of making it were invested into his children.
Prince’s father, John Nelson, had similar dreams of making it as a musician. A talented jazz pianist, he played around Minneapolis with his band, The Prince Rogers Trio. Like Joseph Jackson, however, he also worked tough manual labor to pay the bills — in his case, at a Honeywell plant in Minneapolis. Music was his passion, but the realities of his life made it impossible to fully devote himself to it. Prince grew up watching his father’s disappointment and anger at being unable to realize his dreams. Like Joseph, however, he invested in his children. “I named my son Prince,” John Nelson acknowledged, “because I wanted him to do everything I wanted to do.”
Such aspirations, of course, came at a cost. Both artists experienced abuse and rejection from their fathers. Jackson was infamously forced to rehearse and work like an adult from the age of eight, while Prince was kicked out of his house as a teenager. Both tried desperately to earn the love of their stoic fathers; indeed, in part because of their troubled childhoods, Jackson and Prince worked tirelessly at their crafts. So great was their obsession that it sometimes precluded close, long-term relationships. The music came first. And both were near-messianic in what they felt they could accomplish with it.
The list of similarities goes on: both were lonely, sensitive, sponge-like children; both idolized James Brown, Sly Stone, and Stevie Wonder; both were “crossover” artists, who believed in musical fusion, and surrounded themselves with racially diverse collaborators; both believed in making music visual; both played liberally with notions of race, gender and sexuality, redefining what it meant to be a man; both were private (sometimes reclusive), rarely granted interviews (especially in the ’80s), and created seemingly impenetrable mystiques; both were deeply spiritual, and identified at some point as members of the Jehovah’s Witness faith; both built grand gated personal utopias (Paisley Park and Neverland Ranch); both fought tooth-and-nail against their music labels and the industry as a whole over principles of fair compensation, corporate exploitation, and creative control; both experienced significant commercial and critical declines in the United States in the wake of scandals; and both died unexpectedly and tragically in the midst of artistic comebacks.
In addition to these similarities, however, was another important one: their competitiveness. Both artists were intensely ambitious and made no qualms about where they felt they belonged in the pop hierarchy. They were keenly aware of each other’s albums, tours, awards, and records, and whether they publicly acknowledged it or not, they privately conveyed a desire to match and surpass each other’s achievements, especially in the ’80s.
Prince watched Jackson collect a record haul of eight Grammys in 1984. That stoked his desire to reach similar heights, to be similarly recognized for his work. “We were watching rough cuts of Purple Rain,” remembers Bobby Z, “and we knew that’s where Prince wanted to be the next year.” Later that year, Jackson observed the phenomenon of Purple Rain. He attended a screening of the movie and attended multiple concerts, all the while plotting his return to the throne.
Years later, Questlove remembers sitting with Jackson and Eddie Murphy on the set of a music video when the conversation turned to Prince. “Eddie [was] like, ‘Yeah man… Prince is a bad motherfucker. I’m glad I’m working with you, but another dream I have is working with him too.’” And I don’t even think that Mike knew the camera was on him and he goes, ‘Yes, he’s a natural genius.’ And then four beats later, Michael says, ‘But I can beat him.”
This competitiveness was on full display in a now-legendary game of table tennis between the stars in December 1985. Jackson showed up with his bodyguards at Samuel Goldwyn Studio in West Hollywood, where Prince was putting the final musical touches on Under the Cherry Moon. After some small talk, Prince challenged Jackson to a game of ping-pong. Jackson had hardly played before but said he’d give it a try. Work stopped in the studio as people gathered around to watch the two superstars play.
Prince went easy at first, but before long his competitive streak took over and he began slamming the ball past (and at) a hapless Jackson. “He played like Helen Keller!” Prince later joked to friends. Jackson recovered by chatting up Prince’s then-girlfriend, actress Sherilyn Fenn. “Michael knows how to handle himself,” recalls Prince’s recording engineer, Susan Rogers, “and he didn’t seem to care [about the game]. [He] started flirting with Sherilyn Fenn, who was visiting Prince in the studio. Prince was pacing, but he wasn’t going to get into the game of flirting back. They said hasty goodbyes.”
That year, in an interview with Rolling Stone, Prince boasted: “I wish people would understand that I always thought I was bad. I wouldn’t have got into the business if I didn’t think I was bad.” Perhaps Jackson remembered the quote when coming up with the punctuating quip for his song-in-progress just months later, Who’s bad?
The Secret Meeting
Quincy Jones set up the secret meeting between Jackson and Prince in the summer of 1986. They had discussed concepts in the preceding months, but now things were becoming more concrete. Jackson had a demo finished; its unofficial title was “Pee” (some say it stood for “pressure” — a theme of the song and video — others for its intended collaborator: Prince). The song featured a killer synth bass hook, jazzy organ fills and an exploding chorus. Jackson and his team — including Quincy Jones, manager Frank Dileo, and recording engineer Bruce Swedien — looked on as Prince listened to the track in the control room.
“It was a strange summit,” wrote journalist Quincy Troupe for Spin, “They’re so competitive with each other that neither would give anything up. They kind of sat there checking each other out, but saying very little. It was a fascinating stalemate between two very powerful dudes.”
As Jackson envisioned it, they would begin leaking stories to the press about an escalating rivalry (which wouldn’t be a difficult sell given the media’s already-intense interest in any sign of conflict between the artists). Jackson was enamored with P.T. Barnum at the time and his use of publicity stunts to generate buzz and intrigue. “I want my whole career to be the greatest show on earth,” he told his managers. Earlier that year he had pulled off his first major coup, successfully planting a story about sleeping in a hyperbaric chamber in the National Enquirer (the story was subsequently picked up by media around the world).
Prince, who was no slouch at manufacturing publicity himself, was intrigued but skeptical. He was interested in working with Jackson, but didn’t like the fact that Jackson was in control of the project. He felt Jackson was setting himself up to look better on and off screen. “Prince was like, ‘Oh, he wants to punk me out on record. Who does he think I am, crazy?’” recalls Prince’s manager, Alan Leeds. “He couldn’t get outside himself enough to realize that it was the kind of thing that probably could have benefited both of them. Still, it would have forever been Michael’s video with Prince as just a guest. So that captured what the relationship couldn’t be. They were like Ali vs. Frazier. And the media couldn’t get enough of pitting these guys against each other.”
Prince later explained to comedian Chris Rock of his decision to pass on Bad: “Well, you know, that Wesley Snipes character, that would’ve been me. You run that video in your mind. The first line of that song is ‘Your butt is mine’. Now I said, ‘Who’s gonna sing that to whom? ‘Cause you sure ain’t singing it to me. And I sure ain’t singing it to you… So right there, we got a problem.”
Ultimately, Prince offered a different song in place of “Bad”, reportedly sending Jackson an updated demo of “Wouldn’t U Love to Love Me”, an infectious, Janet-like groove which was later recorded by Prince protege, Taja Sevelle. Jackson, however, decided to pass. Both artists ultimately couldn’t bear to cede control of the project.
As Prince left the legendary “Bad” summit, he turned to Jackson and his team and said graciously, “It will be a big hit even if I’m not on it.” Thus ended the closest possibility of a collaboration between the two legends.
While Prince and Jackson never ended up working together, however, their careers intersected and complemented each other in fascinating ways. In October of 1988, Prince was playing Madison Square Garden while Jackson was at the Meadowlands in New Jersey. The media described it as the “trans-Hudson battle of the bands”. The two shows highlighted each artist’s unique talents and approaches. Jackson’s Bad concert was meant to to be the biggest and the best, to appeal to everyone, black and white, young and old, while Prince’s Lovesexy tour consciously moved outside mainstream pop expectations.
Jackson was the better dancer; Prince was the better musician. Jackson approached live performance with the precision and narrative arc of a film director — everything was highly polished and choreographed. Prince, meanwhile, approached live performance like a jazz musician — he was much more loose and improvisational. Setlists might change, as might performances of songs. Yet both possessed superstar charisma and presence, and both were able to create an ecstatic, almost revival-like feel with their audiences. Like gospel preachers, they generated a reciprocal energy — a call and response — that elicited a transcendent experience for many fans.
The media, of course, often felt compelled to take sides. “Bruce Springsteen may be pop music’s most passionate performer, Prince the most provocative and David Bowie the most theatrical. But Michael Jackson is the field’s most dazzling entertainer,” observed the Minneapolis Star-Tribune’s Jon Bream. Li>The New York Times’ Jon Pareles disagreed. “Where Mr. Jackson asks for the simple exchange of his efforts for the audience’s approval, Prince’s show exults in joyful, risky freedom.” To this day, the debate rages on: Prince played more instruments; Jackson made far superior short films; Prince was a better lyricist; Jackson was a better vocalist; Prince was more prolific; Jackson was a more patient perfectionist; Prince had greater longevity; Jackson had greater cultural impact.
As with all rivalry debates (Stones vs. Beatles, Nirvana vs. Pearl Jam, Janet vs. Madonna, Gaga vs. Beyonce), where one comes down in the end is subjective—and likely reached for more personal reasons. Quincy Jones felt music critics and journalists often used Prince to tear down Jackson rather than recognize each artist’s unique talents and creative visions. Moreover, the media obsession with superiority and conflict often obscured what they accomplished in tandem.
Not only did Jackson and Prince push and challenge each other, they opened doors and set the standard for thousands of artists and entertainers to come. Never before had two African American artists reached such stratospheric heights, shattering pervasive racial barriers on radio, television and film in the process. Both were totally unique, multi-dimensional artists who wrote their own songs, directed their own films, and conceptualized their own performances. Both created vast, diverse catalogs that spanned the spectrum of human emotion and experience. Both became ingrained in the DNA of American (and world) culture with their signature styles, sounds and images. Both challenged and disintegrated traditional borders of identity. Both broke records with their albums, films and world tours.
In the ’80s alone, they produced a combined 30 Top Ten hits, including 13 songs that reached #1. From 1982-1984, Jackson’s Thriller spent a remarkable 37 non-consecutive weeks at #1. It would go on to become the bestselling album of all time, while its music videos revolutionized MTV and reinvented the possibilities of the medium. Prince’s Purple Rain, meanwhile, stayed atop the charts for an incredible 24 weeks — from August 1984 to January 1985 — the fourth longest run in music history. Prince would also become the first artist since the Beatles to have the #1 album, single and movie at the same time.
Neither artist was satisfied with mere commercial success. Their empires were created to protect, cultivate, and advance their creative ambitions. Both ultimately saw themselves as much more than entertainers — they had something to say, and used every means at their disposal to express it.
The King of Pop and His Royal Badness remained competitive to the end. As Jackson prepared for his big comeback at the O2 Arena in London in 2009, he reportedly wanted to make sure his 50-date residency beat Prince’s 2007 record of playing 21 nights to an estimated 350,000 people. Notoriously unable to sleep at night, Jackson told director Kenny Ortega that he was buzzing with creative ideas and couldn’t “turn it off”. Ortega asked if Jackson might possibly put these ideas on hold until after the concert series had begun. “You don’t understand,” Jackson replied. “If I’m not there to receive these ideas, God might give them to Prince.”
Of all people, Prince knew what Jackson meant about being ready and receptive, regardless of when the inspiration came. Like Jackson, Prince was constantly “channeling”, and also had a difficult time turning it off. Asked by Rolling Stone if he was “addicted” to recording music, the artist replied that he felt a compulsive need to “download” what was in his head. “It’s all there,” he explained. “I can hear it all right now. I can hear five albums in my head right now.”
Michael Jackson died on 25 June 25, 2009 — the 25 year anniversary of Purple Rain. Several prominent news websites temporarily froze or crashed due to the overwhelming response. Jackson’s memorial was watched by an estimated one billion people — only the funeral of Princess Diana of Wales compared in terms of audience size. Prince made no public statement, but according to multiple sources, was deeply affected by it. Author and talk show host Tavis Smiley remembers talking to Prince for “for hours… about his own mortality and what the loss of Michael Jackson really meant for him.” Asked about Jackson’s death in an October interview in France, Prince simply said: “It is always sad to lose someone you loved.” On tour, in the ensuing years, he often covered Jackson’s “Don’t Stop ‘Til You Get Enough”. Many years later, in a 2014 interview with Rolling Stone, he was asked to elaborate on his feelings about Jackson’s death, but again declined: “I don’t want to talk about it. I’m too close to it.”
As it turned out, Prince was closer to Jackson than anyone could have anticipated. Like Jackson, his life was cut tragically short in the midst of a creative renaissance. On 21 April 2016, Prince was found unconscious in his Paisley Park elevator. Within hours he was pronounced dead. The news spread rapidly. As with Jackson, the global outpouring was enormous. International monuments were lit purple, as social media timelines filled with memories and tributes. President Obama praised him as “one of the most gifted and prolific musicians of our time… a virtuoso instrumentalist, a brilliant bandleader, and an electrifying performer.”
In the wake of Prince’s death, several journalists revived the rumors of animosity between the artists, reducing their rivalry to a petty celebrity feud. The truth was less sensational. Michael Jackson and Prince respected each other. Yes, they were competitive; no, they were not best friends, but as fellow African Americans, as fellow pioneers, as fellow artists, they recognized each other’s struggles and achievements. They’d travelled similar journeys, after all.
Only a handful of artists change the world: Michael Jackson and Prince were two of them. Had the stars aligned, they would have collaborated on “Bad” back in 1986 or some other incredible project. But as it stands, they both blazed parallel tracks in the ’80s and ’90s, becoming the two most significant artists of a generation.
The pop music world today exists in the shadow of their revolution.
Joseph Vogel is an Assistant Professor of English at Merrimack College. He is the author of the critically acclaimed book, Man in the Music: The Creative Life and Work of Michael Jackson (2011) and the forthcoming monograph, Witnessing the Reagan Era: James Baldwin and the 1980s. His work has appeared in The Atlantic, Slate, The Huffington Post, PopMatters, the F. Scott Fitzgerald Review, The Journal of Popular Culture, the Journal of Popular Music Studies, and Scribner’s Dictionary of American History. He holds a PhD from the University of Rochester.