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The Four Signature Moments of the Prince–Michael Jackson Rivalry

Photo illustration by Slate. Photos by Patrick Kovarik/AFP/GettyImages; Patrick Hertzog/AFP/Getty Images.

In his forthcoming book, Your Favorite Band Is Killing Me: What Pop Music Rivalries Reveal About the Meaning of Life, former Grantland writer Steven Hyden dissects Prince’s colorful rivalry with Michael Jackson.

In the ’80s, Prince reigned as one of the era’s most popular musicians, though he was a relative upstart compared to the decade’s biggest star, Michael Jackson. A brilliant, self-made wunderkind from the Midwest, Prince frequently drew comparisons to the showbiz-bred Jackson. Even now, Prince and Jackson represent a fascinating dichotomy: As much as Jackson seemed intent on catering to his audience, presenting a safe, family-friendly image—this was before anyone accused Jackson of pedophilia, remember—Prince seemed to go out of his way to confound, even antagonize his fans, an approach that served him surprisingly well in retrospect.

If ’80s pop can be likened to high school, Michael Jackson was the prom king who matures into a disappointing adult, whereas Prince was the quirky outcast who blossoms into an impossibly cool grown-up. The two always denied being rivals, but there are four instances in which they clashed.

1. Michael Jackson attempts to show up Prince at a James Brown concert. In 1983, at the Beverly Theater in Los Angeles, James Brown invited Jackson to appear onstage and blow Brown’s mind with his perfectly executed James Brown dance moves. After that, MJ whispered in JB’s ear, and all of a sudden Prince magically materialized onstage and did his James Brown moves and shredded a little on a guitar. The footage is fuzzy, but its awesomeness can’t be denied: it’s like watching three faces on America’s funky Mount Rushmore come to life and duel it out.

What’s interesting about the video is that members of Prince’s entourage were convinced that MJ intended to humiliate Prince, and (in their view) he succeeded. “He played a few licks, did some dancing and knocked over a prop by accident,” Alan Leeds told Vibe. “[Prince’s drummer] Bobby Z called and said, ‘Oh boy … he made an ass of himself tonight.’” But as a mortal watching the video, I don’t think Prince looks like an ass; he looks like a god showing off for two other gods.

2. Prince bails on the recording session for “We Are the World.” In retrospect, backing out of recording “We Are the World,” a maudlin exercise in instantly dated limousine liberalism, seems like a wise decision. (At least there is no embarrassing footage of him on YouTube singing between Kenny Rogers and Kim Carnes.) But at the time, not doing “We Are the World” was a major PR disaster. Prince was viewed as a conceited jerk, whereas Michael Jackson was depicted as selfless for spearheading the project. Reports that Prince didn’t show up because he was waylaid by an altercation between a photographer and his bodyguards outside a Mexican restaurant on the Sunset Strip led to the bizarre, only-in-’85 indignity of Billy Crystal impersonating Prince on a Saturday Night Live parody called “I Am the World.” That’s right: Prince was so reviled over “We Are the World” that Billy Crystal in blackface was considered an appropriate corrective.

3. Prince beats Michael Jackson at ping-pong. Jackson famously paid Prince a visit while Prince worked on Under the Cherry Moon, his ill-fated cinematic follow-up to Purple Rain. Always a hospitable host, Prince invited Jackson to play ping-pong. “I don’t know how to play, but I’ll try,” Jackson replied.

Naturally, all the bystanders stopped what they were doing and watched the game, as this surely was the single most electrifying ping-pong match ever. As eyewitnesses later recounted, it started with some soft hits back and forth. Then Prince said, “Come on, Michael, get into it.” Then Prince taunted MJ again: “You want me to slam it?”

What happened next represents the most iconic moment in the history of sporting events between ’80s musical icons: Jackson dropped his paddle, and Prince slammed the ping-pong ball into MJ’s crotch. After Jackson left, Prince was justifiably feeling himself. “Did you see that?” he declared, according to Ronin Ro’s Prince: Inside the Music and the Masks. “He played like Helen Keller!”

4. Prince declines to duet with Michael Jackson on “Bad.” MJ envisioned it as a can’t-miss publicity stunt, with both singers’ camps hurling fake insults at each other in the media until the single dropped. Prince supposedly considered going along with it, but he balked at the song itself: He didn’t want to be the one who says “Your butt is mine” to Michael Jackson, and he didn’t want Michael Jackson singing the lyric to him. I’m very upset that this duet didn’t happen, but I can’t argue with Prince’s reasoning.

Something unexpected happened to Michael Jackson and Prince by the dawn of the 21st century: Jackson was so weird that he was only barely a pop star, whereas Prince was relatively less weird, which allowed him to stage a comeback. In the familiar “pathetic geek” celebrity narrative, it was as if Prince had finally matured into “normal” adulthood. On his 2004 Musicology tour, his first tour in six years, Prince satisfied millions of fans by playing his hits relatively straight, save for a misplaced curse word or two. (Prince’s religious beliefs prompted him to tone down the songs.) Meanwhile, on Chappelle’s Show, Dave Chappelle made Prince’s ’80s spikiness appear cuddly and endearing, a full 180 from the way those attributes were perceived two decades earlier, when Prince was in his mocked-by-blackface–Billy Crystal doldrums.

Now Jackson was the one who suffered in comparison. His story was the flip side of the pathetic geek narrative—the former prom king who grows up to be a weirdo loser. Even Prince took shots at MJ in the mid-aughts: “My voice is gettin’ higher / And I ain’t never had my nose done / That’s the other guy,” he sings on “Life o’ the Party” from Musicology.

 “I was a fan my whole life. [But] I’m fucking done,” Chris Rock said of Jackson in his 2004 stand-up special, Never Scared. “Remember when everybody used to have those arguments about who’s better, Michael Jackson or Prince? Prince won.”

Read more from Slate on Prince.

Excerpted from Your Favorite Band is Killing Me by Steven Hyden, copyright ©2016 by Steven Hyden.  Used with permission by Little, Brown and Co., New York.  All rights reserved.