If we can thank/blame anyone for the state of modern pop fame, it’s Michael Jackson, Madonna and Prince. In the early 1980s, as MTV fused a new form of music consumption with a heightened awareness of celebrity culture, they emerged as America’s holy trinity.
All three singers were born to complicated childhoods in the spring/summer of 1958, and each became preeminent visual artists who reinvented themselves as the years progressed. Jackson, of course, had a built-in audience thanks to his already lengthy career, but 1979’s “Off the Wall” and 1983’s “Thriller” redrafted his legacy as a dazzling solo artist. Prince and Madonna, arriving to grown-up stardom in 1978 and 1982, respectively, built reputations as iconoclasts challenging standard notions of gender and sexuality.
As these things go, the media loved to adjudicate the trio’s stature, seizing opportunities to report on their interactions. They were often portrayed, somewhat inflatedly, as archrivals. At times, they were friends. Elsewhere, they seemed like resentful competitors hell-bent on outpacing one another.
I spent weeks combing through news stories that mention two or more of them, and you can’t imagine the number of times the press questioned how long their careers would last. Madonna, willing to give ample interviews and use the media to mold her image, was the most vocal of the three. So much so that, at times, she repeated herself. Jackson seemed the most starved for affection, regularly pitching collaborations that Prince declined. Prince himself was, unsurprisingly, the most enigmatic ― an androgynous prodigy whose fierce independence may have sometimes gotten the best of him. Where Madonna is one of the savviest self-marketers that popular culture has ever seen, Prince leaned into his aloof stylings as The Purple One and Jackson became a virtuoso haunted by a Peter Pan persona. Most importantly, each understood that pop music is both an art and a business.
As a case study in contemporary celebrity, below is a comprehensive list of all the times Madonna, Prince and Michael Jackson interacted, teamed up, sparred or spoke of one another publicly, along with a few interesting points that writers raised about their cultural impact along the way. All your favorite rumors are here, as long as they stem from reputable publications or unauthorized biographies. Settle in for 33 years of romances, catfights, collaborations, tributes and complicated kindredness. It’s all flown by faster than a ray of light.
1983: James Brown invites Jackson onstage with him. After Jackson dazzles with his dance moves, he whispers in Brown’s ear and then Brown invites Prince, who shares a tour manager, to join. Prince and his entourage are convinced that Jackson intended to humiliate Prince, whose guitar malfunctions during the performance.
1983: Seeking a manager, Madonna enlists Freddy DeMann because he also manages Jackson, whom Madonna deems the “most successful person in the music industry.” DeMann attends a show Madonna performs at Studio 54. “I was so nervous because Michael Jackson’s so incredible live and I thought, ‘If he thinks Prince is terrible ― which he did ― what can I do?’” she later said. “Then he liked the show.”
Feb. 28, 1984: At the first Grammy Awards where Jackson and Prince compete for the same accolades, Jackson’s “Billie Jean” tops Prince’s “International Lover” for Best Male R&B Vocal Performance. Jackson’s “Thriller” beats Prince’s “1999” for Best Male Pop Vocal Performance.
July 1984: Wanting to assess his competition, Prince and his crew attend a Dallas stop on The Jacksons’ Victory Tour. “There was a feeling in our camp that, while what they were doing was a very solid stadium production, there was nothing really cutting edge about the technology,” Alan Leeds, Prince’s tour manager, told Vibe in 2010. “Prince had a lot of respect for Michael, but he was mildly impressed with the show.”
September 1984: Teen magazine Right On! puts Jackson and Prince on the same cover with the headline “Who Rules The Music Kingdom? Prince Or Michael?” “Michael and Prince were not actually battling each other on a serious level,” then-editor Cynthia Horner said in 2010. “But because I knew that was something the public found fascinating and everybody always talked about it, I wanted to have both of them on the cover together to project that element of Prince vs. Michael.”
Sept. 2, 1984: A New York Times essay contrasts Jackson and Prince’s top-tier superstardom in detail, noting their androgyny and race-bending success: “If Mr. Jackson’s message is ‘all you need is love,’ Prince’s amounts to ‘all you need is sex.’”
December 1984: On the Australian music series “Countdown,” journalist Molly Meldrum asks Madonna how she feels about being called the “female Michael Jackson.” She laughs and responds, “That’s nice. That’s flattering.”
Dec. 2, 1984: “Sure, I can relate to him because he has a chip on his shoulder,” Madonna says of Prince in a Los Angeles Times interview. “He’s competitive, from the Midwest ... a screwed-up home and he has something to prove. I can relate to that ― totally.”
Late 1984 and early 1985: Jackson attends multiple stops on Prince’s Purple Rain Tour.
Jan. 28, 1985 (part 1): Prince spots Madonna backstage at the American Music Awards, reportedly asking his manager to collect her phone number. She later presents him with the prize for Favorite Black Album (yes, that was a thing). The next day, according to Christopher Andersen’s unauthorized Madonna biography, Prince calls Madonna to ask her out on a date. She attends a night of his Purple Rain Tour, shortly before her inaugural Virgin Tour is set to launch. They carouse on and off for a few months whenever Madonna is in Los Angeles, but along the way, Madonna meets future husband Sean Penn and the rumors of her Prince liaison are put to bed.
Years later, Prince’s friend T.L. Ross tells Madonna: An Intimate Biography scribe J. Randy Taraborrelli that Madonna saw sex as a “physical experience” and Prince saw it as a “cosmic” one. In keeping, Prince found Madonna too aggressive. Madonna also thought he “reek[ed]” of lavender, but it turned her on. “After he stopped acting interested in her, that’s when the phone calls started,” Ross said. “Madonna pestered him for weeks. He said later that she screamed at him, ‘How dare you dump me? Don’t you know who I am?’ She was definitely not used to getting dumped.” Freddy DeMann’s assistant told Taraborrelli that Penn punched a hole in Madonna’s wall after discovering she had dated Prince. She phoned Prince to repair it: “You’re responsible for it, after all,” she told him.
Jan. 28, 1985 (part 2): Prince’s “Purple Rain” beats Michael Jackson’s “Thriller” for Favorite Pop/Rock Album and Favorite Black Album at the American Music Awards. Later that night, a horde of A-list musicians record the famous “We Are the World” charity single, which Jackson has overseen with Lionel Richie and Quincy Jones. Prince and Jackson are supposed to have a verse that they sing to each other (the two had met for lunch, as organized by Jones), but Prince is a no-show. He wants to contribute a different song to the charity endeavor, send Sheila E. in his place and/or play guitar on “We Are the World,” which Jones vetoes.
At least one report indicates Prince did not want to record with the other musicians, while another says he was upset because Bob Geldof had called him a “creep.” Either way, Prince is spotted at a Hollywood club later that night, against his manager’s advisement. In the 2014 book Let’s Go Crazy: Prince and the Making of “Purple Rain,” the singer’s backing guitarist Wendy Melvoin says, “I wasn’t allowed to say the real reason: Because 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 and he didn’t want to be around ‘all those muthafuckas.’”
April 10, 1985 – June 11, 1985: During her Virgin Tour, Madonna incorporates a bit of Jackson’s “Billie Jean” into her performance of “Like a Virgin,” highlighting their similar bass lines.
April 23, 1985: That song Prince said he’d donate to the “We Are the World” album? It’s there, and it’s called “4 the Tears in Your Eyes.”
May 13, 1985: A People article denies rumors that Madonna and Prince were ever romantically involved, reporting that she once called him a “midget” as she arrived at a date in San Francisco. “He usually wants to be treated the exact opposite of the way he is dressed,” Madonna says. “His outfits say touch me, lick me, love me, lust me, but then he pretends he’s wearing a monk’s outfit. He needs to step back, look at his clothing and laugh at it.”
July 1985: Riding the success of “Desperately Seeking Susan,” Madonna bags her next movie role, the Warner Bros. musical “Street Smart.” Michael Grais, the film’s writer, says he also has his eye on a role for Prince protégée Vanity. The movie never comes to fruition.
July 10, 1985: Prince releases a B-side called “Hello,” on which he tells his side of the “We Are the World” incident. The first verse says “I tried to tell them that I didn’t want to sing / But I’d gladly write a song instead / They said OK and everything was cool / Till a camera tried to get in my bed.”
Sept. 19, 1985: The Parents Music Resource Center, formed the previous year by Tipper Gore and three other politicians’ wives, testifies about foul lyrics in a Senate hearing. Susan Baker co-founded the organization after her 7-year-old daughter heard Madonna’s “Like a Virgin” and asked what “virgin” meant. Earlier in 1985, the PMRC had released the “Filthy Fifteen,” a list of objectionable songs they hoped to ban from radio airwaves. The list included Madonna’s “Dress You Up” and Prince’s “Darling Nikki.” By the time the hearings are over, the PMRC has established the “parental advisory” label.
Circa 1986: Prince is working on “Under the Cherry Moon,” his ill-fated follow-up to the movie “Purple Rain,” when Jackson pays him a visit. Prince challenges his competitor to ping-pong. Jackson doesn’t know how to play, and amid taunts from Prince to step up his game, Prince slams the ball into Jackson’s crotch. After Jackson leaves, Prince says Jackson played like Helen Keller.
1986: Jackson writes “Bad,” and producer Quincy Jones sees it as a potential duet with Prince, who is supposedly on board until realizing it would require him to sing the lyric “Your butt is mine” to Jackson. “Don’t worry, this record will be a big hit even if I’m not on it,” Prince says at the time, according to producer Bruce Swedien. In a 1997 VH1 interview with Chris Rock, Prince confirms these rumors but states that he sees no rivalry with Jackson. It is later revealed that Prince gifted him with a box of voodoo artifacts, and Jackson was convinced that Prince was trying to cast a spell on him.
Feb. 25, 1987: Madonna releases “La Isla Bonita,” which becomes a Top 10 hit. Composed by Patrick Leonard, who served as the musical director on The Jacksons’ Victory Tour and Madonna’s first two tours, the musical track of “La Isla Bonita” was first pitched to Jackson. He passed on it.
December 1987: Jackson is rumored to be “infatuated” with backup singer Siedah Garrett, who contributed vocals to Madonna’s “True Blue” album and recorded “I Just Can’t Stop Loving You” with Jackson as a duet on his “Bad” album.
December 1987: Railing against criticisms of her sexualized image, Madonna tells Smash Hits magazine, “I think, ‘Why aren’t they letting this stand in the way of appreciating Prince’s music?’” She reasons that some women don’t like her because “they’re taught that to be strong and respected they had to behave like men or not be sexy or feminine and it pissed them off that I was being that.”
1988: In audio that surfaced in 2016, Jackson allegedly says he doesn’t like to be compared to Prince, calling him “rude” and “nasty.” “I have proven myself since I was real little,” Jackson is heard saying. “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.”
May 1988: Movie producer Dodi Fayed, who later died in a car accident with Princess Diana, says he turned down interest from both Jackson and Madonna to play Peter Pan in a live-action movie. “When I was told Madonna wanted to be Peter Pan, I laughed,” Fayed tells the Los Angeles Times. “I just doubted whether anyone would know her in a few years. I wouldn’t use Michael Jackson now either because I think there’s a real danger he won’t be popular in a few years.”
Oct. 9, 1988: The week that Prince and Jackson are slated to perform individually at the same venue in Maryland, The Washington Post prints an essay comparing their fame, labeling Prince the critical darling and Jackson the populist champ.
March 21, 1989: Madonna’s “Like a Prayer” album is released, featuring a sultry duet with Prince, “Love Song.” The collaboration comes to be after Prince presents demos of songs they’d recorded together via phone to Madonna backstage during her 1988 Broadway debut in David Mamet’s “Speed-the-Plow.” “We were friends and talked about working together, so I went to Minneapolis to write some stuff with him, but the only thing I really dug was ‘Love Song,’” she later said. “We ended up writing it long-distance, because I had to be in LA and he couldn’t leave Minneapolis, and quite frankly I couldn’t stand Minneapolis. When I went there, it was like 20 degrees below zero, and it was really desolate. I was miserable and I couldn’t write or work under those circumstances.” The New York Times’ review of the album calls “Love Song” “smoldering.” Prince also plays guitar, uncredited, on three other tracks: “Like a Prayer,” “Keep It Together” and “Act of Contrition.”
Sept. 6, 1989: Madonna’s “Express Yourself” tops Jackson’s “Leave Me Alone” for the Viewer’s Choice prize at the MTV Video Music Awards. Both lose to Neil Young’s “This Note’s for You” for Video of the Year.
Oct. 2, 1989: Jackson’s $125 million net worth tops Forbes’ annual list of the richest entertainers, while Madonna sits at No. 15 with $43 million and Prince places at No. 20 with $36 million.
Oct. 13, 1989: The Los Angeles Times prints a list of the celebrity clientele at the Ritz-Carlton. Jackson and Madonna are both on it.
Early 1990s: While giving producers L.A. Reid and Kenny “Babyface” Edmonds a tour of Neverland Ranch, Jackson stops in his screening room to show the producers footage of Prince’s guitar malfunctioning during their 1983 performance with James Brown. He then plays a scene from Prince’s “Under the Cherry Moon,” mocking both clips.
Nov. 2, 1990: “Graffiti Bridge,” a critically derided sequel to “Purple Rain,” opens in theaters. According to Matt Thorne’s Prince: The Man and His Music, published in 2016, Prince wanted Madonna to play his love interest in the movie, but she “didn’t consider the script worthy of her talents.”
January 1991: Madonna and Jackson reportedly join an all-star cover of John Lennon’s “Give Peace a Chance,” organized by Yoko Ono in response to the Gulf War. Neither winds up appearing on the track, which instead features the likes of Cyndi Lauper, Tom Petty, Bonnie Raitt, Lenny Kravitz and MC Hammer.
March 16, 1991: Madonna and Jackson dine together at Los Angeles hotspot Ivy. The restaurant’s employees spend the night warding off paparazzi.
March 25, 1991: Madonna and Jackson attend the Oscars together, where Madonna ― who arrived dressed like Marilyn Monroe ― performs “Sooner or Later” from the movie “Dick Tracy.” They sit in the front row and attend talent agent Swifty Lazar’s after-party together, where they reportedly carouse with Michael Douglas, Warren Beatty, Anjelica Huston, Robert Graham and Diana Ross. The following year, Madonna says she had tried to get Jackson to cut his long hair before the event.
April 1991: Madonna tells The Advocate that she’d like to “completely redo” Jackson’s image. “I also want to get him out of those buckly boots and stuff,” she said. She wants Jackson to spend time with the House of Xtravaganza, a queer New York ball group that helped to inspire her 1990 hit “Vogue.”
May 1991: “She just isn’t that good,”Jackson says of Madonna in the unauthorized biography Michael Jackson: The Magic and the Madness. “Let’s face it, she can’t sing and she’s just an OK dancer. What does she do best? She knows how to market herself. That’s it.” The book also claims Jackson envied Madonna’s fame, especially after MTV named her its Artist of the Decade. (He arranged for MTV to present him with an award called the Video Vanguard Artist of the Decade.) “That’ll teach the heifer,” he reportedly says.
Oct. 17, 1991: In a USA Today article, Sister 2 Sister owner Jamie Foster Brown describes a birthday party that Jackson and Madonna had attended at a restaurant. “Michael pushed the birthday candles away from his face when they sat down,” she says. “Madonna came up and snatched the glasses off his face and threw them across the room. ‘Tonight, you’re going to be normal like the rest of us,’ she shouted. Madonna said that when they first met, Michael would stare at her breasts so hard that she took his hands and put them on her. He said, ‘Oh, no, you can’t do that.’”
Nov. 19, 1991: In a TV Guide Magazine interview, Madonna says she likes Prince’s music, but his videos are “silly and cheap and below his ability.”
Dec. 14, 1991: “They are fans of each other,” Liz Rosenberg, Madonna’s publicist, tells the Los Angeles Daily News, referring to the singer’s relationship with Jackson. “She is an entity unto herself. There is room for two big stars.”
April 8, 1992: Jackson releases “In the Closet,” which was originally intended as a collaboration with Madonna. In an interview with Jonathan Ross, Madonna says the two singers had a meeting where Jackson played a demo of the song. She asked whether he knew what the phrase “in the closet” implied, and when Jackson said yes, she offered some lyrical suggestions. “I presented them to him and he didn’t like them,” she tells Ross. “I think all he wanted was a provocative title and ultimately he didn’t want the contents of the song to live up to the title.” For the potential video, Madonna reportedly wanted to dress in male drag, with Jackson sporting female drag, but Jackson refused. Jackson instead records “In the Closet” with Princess Stéphanie of Monaco, whose vocals are initially mistaken for Madonna’s.
Sept. 4, 1992: Reports indicate that Prince’s $100 million contract with Warner Bros. ― which makes him one of company’s vice presidents ― is the biggest for a recording star in history. Newsday points out that it tops $60 million deals recently signed by Madonna and Jackson. Industry insiders express skepticism at the price of Prince’s contract.
Sept. 9, 1992: Jackson signs on to perform at the Super Bowl XXVII halftime show on CBS. Fox attempts to recruit Madonna to perform in the same time slot, but she does not want to compete against Jackson.
March 1993: While shooting the video for Jackson’s collaboration with Eddie Murphy, “Whatzupwitu,” Murphy is seen saying he would love to collaborate with Prince, as well. “Yes, he’s a natural genius,” Jackson replies. “But I can beat him.”
March 24, 1993: Madonna is spotted chatting with Whitney Houston during a Prince concert at Radio City Music Hall.
October 1994: In an interview with London’s Evening Standard, Madonna says this of Prince and Jackson, who are growing ever more elusive in the media: “Prince’s demure behavior and Michael Jackson’s running away from the truth is much more revealing about them than any of the things I’ve told. I could talk to you for hours and you could read all my interviews, but you’d never feel you completely knew me. If they would just come outside and mingle with humanity, everything would benefit ― their art, and whatever relationships they may have. I’ve spent a good deal of time with both of them. They have these manners and they’re just so careful about what they eat and what they say. It’s never too late to start being a human being. Forget salvation in the public eye. I’m just talking about being happy in your private life.”
October 1994: In an interview with the BBC, Madonna says, “I’m being punished for being a single female, for having power and being rich and saying the things I say, being a sexual creature ― actually, not being any different from anyone else, but just talking about it. If I were a man, I wouldn’t have had any of these problems. Nobody talks about Prince’s sex life, and all the women he’s slept with.”
October 1994: In an interview with the Los Angeles Times, Madonna says, “I could never say that either of them were friends. I’ve spent a good deal of time with both of them. They’re very different people, but I felt the same with both. I felt like a peasant next to them, like this big clumsy farm girl. Like, when I’m hungry, I eat. When I’m thirsty, I drink. When I feel like saying something, I say it. And they have these manners and they’re just so careful about what they eat and what they say. I had dinner with Prince once, and he was just sipping tea, very daintily. I was stuffing food down my face and I was like, ‘Aren’t you going to eat?’ And I thought, ‘Oh my God!’ I have this theory about people who don’t eat. They annoy me. It’s something about being in control.” Here, she starts to repeat herself. “It’s never too late to start being a human being. If they could just try being something close to that, then that would be the way to ... I mean, [forget] salvation in the public eye ― I’m just talking about being happy in your private life. Just being able to go to a basketball game or for a bike ride. I can’t imagine either of those guys putting on sweat pants and sneakers and going for a run, playing outside with a dog or just being silly and hanging out with your friends without your makeup on. You know what I mean? I don’t think they do that.”
Feb. 13, 1995: “Michael Jackson and Madonna are the torchbearers of American society; their cultural and social values are destroying humanity,” says Nematullah Khan, a divisional chief of the Party of Islam group, which wants the singers to be tried as terrorists in Pakistan.
July 10, 1995: A report in the Daily Mirror says that Elizabeth Taylor, a close friend of Jackson’s, invited Prince to dinner, much to Jackson’s disdain. Taylor was displeased when Prince arrived with security detail. After Prince refused to leave his bodyguards behind, Taylor went to bed instead of dining with the singer, leaving him to socialize with her husband. “Liz sent the doves Prince gave her back, and never heard from him again,” a source tells the paper.
Fall 1996: As both artists deal with the aftermath of personal blows (Jackson’s child-molestation accusations and Prince’s heated dispute with his record label), Jackson instructs his handlers to contact Prince about a potential collaboration. “I think it would be just great,” Jackson reportedly tells Prince over the phone. The joint effort never materializes.
Feb. 16, 1997: Jackson sings a song he wrote for Elizabeth Taylor during a Hollywood birthday bash that doubles as an AIDS benefit. Madonna is also on hand, toasting Taylor with a speech and escorting her to the stage. (The event is televised on ABC the following month.)
Sometime in 1998: “I respect any artist who has talent, and Michael Jackson and Prince are extremely talented artists,” Madonna tells The Sunday Mail, as printed in an April 11, 1999, article about J. Randy Taraborrelli’s yet-to-be-released Madonna: An Intimate Biography, which reasserts that Prince and Madonna had a two-month affair in 1985. “I do not care what they do out of the spotlight ― that’s their business ― but I do hope they continue to do good work. I am a fan.”
May 21, 1998: After several years of public imbroglio regarding Prince’s Warner Bros. contract (WB terminated Paisley Park Records in 1993 and he became The Artist Formerly Known as Prince), Liz Jones’ Slave to the Rhythm is published. The book says Madonna, wanting to help, proposed that Prince’s NPG Records merge with her Maverick Records. Nothing comes of the offer.
July 1998: Madonna cites Prince’s “When Doves Cry” as a song she would “escape into” as an emerging recording artist. “By then I did have a record contract, and I had moved to a nice loft on Broome and West Broadway,” she tells Rolling Stone in a cover story. “But there was still no elevator, so I had to walk up six flights of steps to get to my loft. I rode my bike everywhere, with a Walkman and headphones on, and one hot summer day I came in and I just couldn’t carry my bike up those stairs one more time. I was hating my family and my life at the time, and I just collapsed in the stairwell with that song playing in my headphones, crying my heart out and feeling incredibly sorry for myself.”
Nov. 24, 1998: As Prince’s 1982 hit “1999” gets remixed for the impending year, a New York Post story indicates Jackson offered to record the song with him as a duet.
Jan. 19, 1999: In an open letter to Madonna on his website, Prince says he had a dream in which he asked her to speak out against Warner Bros., which still will not relinquish the rights to Prince’s back catalog.
September 1999: After the 1997 remix album “Blood on the Dance Floor” sees weak sales, Jackson re-signs with Freddy DeMann, who had managed him throughout the 1970s and ‘80s. DeMann had split with Madonna earlier that year.
November 1999: In a ranking released by MTV and TV Guide, Michael Jackson’s “Thriller” is named the best music video since the launch of MTV in 1981. Madonna’s “Vogue” is No. 2. Both have two other clips on the list: Madonna’s “Express Yourself” (No. 10) and “Lucky Star” (No. 50), and Jackson’s “Beat It” (No. 12) and “Billie Jean” (No. 35).
May 2, 2001: VH1 ranks the 100 greatest music videos of all time. Madonna, whose “Like a Prayer” is No. 2, boasts six items on the list, more than any other artist. Jackson, whose “Thriller” is No. 1, has five. Prince has two.
November 2001: An unauthorized Madonna biography says Madonna tried to seduce Jackson after the 1991 Oscars but “nothing happened because he was giggling so much.”
April 2003: In a Q Magazine interview, Madonna slams “Living with Michael Jackson,” the documentary that chronicles the King of Pop’s odd parenting behavior and changing appearance. “It sounds disgusting, like [journalist Martin Bashir] exploited a friendship,” she says. “Publicly humiliating someone for your own gain will only come and haunt you. I can assure you, all these people will be sorry. God’s going to have his revenge.” In a “Dateline NBC” interview with Matt Lauer that same month, Madonna says she hasn’t talked to Jackson “in ages,” but she calls the documentary “exploitive.”
Oct. 17, 2005: Madonna’s “Hung Up” is released, borrowing a hook (and the lyric “Time goes by so slowly for those who wait / And those who run seem to have all the fun”) that she and Prince used on “Love Song.”
Late 2006: Will.i.am arranges for Jackson to attend a show during Prince’s Las Vegas residency. Prince knows where Jackson will be seated, and he emerges into the crowd and aggressively plays bass in Jackson’s face. Jackson is outraged, reportedly telling will.i.am the next day, “Prince has always been a meanie. He’s just a big meanie. He’s always been not nice to me. Everybody says Prince is this great legendary Renaissance man and I’m just a song-and-dance man, but I wrote ‘Billie Jean’ and I wrote ‘We Are the World,’ and I’m a songwriter too.”
May 31, 2007: Already committed to perform 21 shows at London’s O2 Arena, Prince turns down an invitation to join Jackson on a planned comeback tour. “Michael seemed pretty disappointed about it,” a source reportedly tells Britain’s The Sun.
Aug. 1, 2007: “I got so many hits, y’all can’t handle me. I got more hits than Madonna’s got kids,” Prince quips during a London concert. Rumors of a feud swirl.
June 25, 2009: Jackson dies at age 50. Madonna’s manager, Guy Oseary, reveals Madonna was planning to join Jackson onstage on one night of his 50-show residency at London’s O2 Arena.
June 25, 2009: Speaking to the Star Tribune in Minneapolis following Jackson’s death, drummer Michael Bland says Prince and Jackson’s rivalry was overstated. “They’d shoot hoops at Paisley Park,” he tells the newspaper.
June 26, 2009: Madonna releases a statement about Jackson’s death: “I can’t stop crying over the sad news. I have always admired Michael Jackson. The world has lost one of the greats, but his music will live on forever! My heart goes out to his three children and other members of his family. God bless.”
July 4, 2009: Days before Jackson was supposed to start his O2 Arena residency, Madonna and the backup dancers on her Sticky & Sweet Tour perform a medley of “Billie Jean” and “Wanna Be Startin’ Somethin’.” “Let’s give it up for one of the greatest artists the world has ever known, Michael Jackson,” Madonna tells the crowd.
July 7, 2009: Oseary says Madonna, who just kicked off the European leg of her Sticky & Sweet World Tour after a lengthy hiatus, has been dedicating her shows to Jackson.
Sept. 13, 2009: Madonna opens the MTV Video Music Awards with a tearful tribute speech about Jackson, worrying network president Van Toffler that her speech would be too serious. “I can’t say we were great friends, but in 1991 I decided I wanted to get to know him better,” she said. “I asked him out to dinner: I said, ‘My treat, I’ll drive, just you and me.’ He agreed and showed up to my house without any bodyguards. We drove to the restaurant in my car. It was dark out, but he was still wearing sunglasses. I said, ’Michael, I feel like I’m talking to a limousine, do you think you could take off those glasses so I could see your eyes?’ He paused for a moment, then he tossed the glasses out the window, looked at me with a wink and a smile and said, ’Can you see me now, is that better?’ In that moment, I could see both his vulnerability and his charm. The rest of the dinner, I was hell-bent on getting him to eat french fries, drink wine, have dessert and say bad words, things he never seemed to allow himself to do. Later, we went back to my house to watch a movie and we sat on the couch like two kids, and somewhere in the middle of the film, his hand snuck over and held mine. It felt like he was looking for a friend more than a romance and I was happy to oblige him. And in that moment he didn’t feel like a superstar, he felt like a human being. ... Yes, Michael Jackson was a human being, but he was a king. Long live the king.”
Sept. 25, 2009: The Michael Jackson Tapes: A Tragic Icon Reveals His Soul in Intimate Conversation ― a book that Shmuley Boteach, Jackson’s spiritual adviser, publishes after Jackson’s death ― includes Jackson reportedly saying he thought Madonna was jealous of his success and “sincerely” in love with him. “She hasn’t been kind,” he says. The book also recounts Madonna not wanting to go to Disneyland, Jackson not wanting to go to a strip club, and Madonna waving away a young fan who approached the two of them while they were dining: “We were at the table eating, and some little [kid] came up, [saying] ‘Oh, my God, Michael Jackson and Madonna!’ She goes, ‘Get out of here. Leave us alone.’ I said, ‘Don’t you ever talk to children like this.’ She said, ‘Shut up.’ I said, ‘You shut up.’ Yes, that’s what I said. Then we went out again and went to the Academy Awards and she is not a nice person.”
July 2010: While photographing Prince for the cover of Ebony magazine, Dudley Brooks talks to the singer about being a Jehovah’s Witness ― a religion that Jackson also once subscribed to. Prince tells Brooks that he and Jackson discussed the difficulties of balancing religion and fame, and that he wishes he’d spoken to Jackson about the struggles before he’d died.
October 2010: “When I saw Prince a few years back, he was giving my uncle props and saying how much he loved his voice,” Austin Brown, Michael’s nephew, says in an interview. “So I don’t know how true it is that they didn’t get along because that’s not what I saw.”
Jan. 18, 2011: Madonna attends a Prince concert at Madison Square Garden, where she is spotted singing and clapping along to the performance. “Prince and Madonna End Decades-Long Feud,” Rolling Stone trumpets, reporting that Prince gave Madonna a “friendly call-out by name” during the show.
October 2011: In I Want My MTV: The Uncensored Story of the Music Video Revolution, a wide-ranging oral history of the network’s first decade, director John Landis says he asked Jackson to stop grabbing his crotch while making the 1991 video for “Black or White.” “Madonna does it, Prince does it,” Jackson apparently told him, to which Landis responded, “You’re not Madonna or Prince. You’re Mickey Mouse.”
January 2013: “It was also about Madonna,” Prince tells Billboard magazine in a cover story, referring to the origins of his dispute with Warner Bros. in the ‘90s. “She was getting paid, but at the time we were selling more records and selling out concerts on multiple nights.” He clarifies that it wasn’t Madonna’s fault: “It wasn’t about her. This was about business.”
April 2013: Prince — along with Diana Ross and Spike Lee — appear on the list of celebrities who could be called to testify in Jackson’s wrongful-death trial. (He is not called.)
March 6, 2015: Madonna releases “Rebel Heart.” The album features the song “Iconic,” on which Chance the Rapper raps, “Madonna said I remind her of Michael.”
Oct. 8, 2015: After a Minnesota stop on her Rebel Heart Tour, Madonna and her touring crew attend an intimate jam session at Prince’s Paisley Park studios. They arrive at 1:30 a.m., and Prince — accompanied by Madonna — emerges at 2:15. She sits in a roped-off VIP section to watch him perform. Around 3 a.m., the singers whisper something to each other and Madonna and her crew take off. A local radio station says Prince appeared “awestruck” by Madonna.
April 21, 2016: Prince dies at age 57. Jackson’s Twitter account posts a memorial for the singer.
April 21, 2016: Madonna posts a memorial for Prince on Instagram.
April 22, 2016: Guy Oseary, Madonna’s manager, reveals in an Instagram post that he pitched Prince and Madonna on doing a joint tour “a few years back.” Madonna agreed instantly, suggesting they call it the Royalty Tour. Prince, on the other hand, said, “The world isn’t ready for this. It’s too big.”
April 26, 2016: “Nobody better understands that merging of video and music than he did,” Alan Leeds, a longtime Prince confidante, tells Rolling Stone. “Well, I shouldn’t say nobody: obviously Madonna did and Michael [Jackson] did and so on. But he was amongst the first.”
May 4, 2016: Madonna posts another Prince tribute on Instagram.
May 22, 2016: Madonna performs “Nothing Compares 2 U” and “Purple Rain” at the Billboard Music Awards. Some fans are upset that she is the one selected to tribute Prince. Madonna responds on Instagram.
May 24, 2016: Anna Fantastic, Prince’s ex-girlfriend, tells TMZ that Prince turned down an invitation to make a video for “Love Song,” his collaboration with Madonna. “I think he liked the song, but didn’t want to do a video,” she said. “I even said, ‘I think you and Madonna in a video could be really cool, and he said, ‘Me and Madonna in a video? No thanks.’”
May 28, 2016: Madonna posts an Instagram photo sporting a jacket Prince gave her “back in the day.” She takes a jab at BET, which insulted her Billboard tribute.
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