The King of Pop. The Gloved One. Wacko Jacko. Call him what you want. Michael Jackson was viewed as an icon of his generation and even in death, so many critics and fans still view him as one of the most talented names to ever moonwalk onto the music industry. All things considered, he'd make for quite the catch as a partner.
Particularly due to the damning allegations against him, people forget that women were wooed by MJ's lyrics and were in awe of the man. His aesthetic appeal was evident and people flocked to him for it. Even plenty of those within the entertainment industry flocked to him for that reason. His love life is just as interesting as whatever hypothetical relationships or rumors the media may have cooked up for him back in the day. So with all that in mind, let's take a trip down memory lane at some of Michael Jackson's old relationships, as well as mention some women who even he did not have a shot with.
20 No Chance - Cher
Cher worked with Michael Jackson back when he was still just a young member of the Jackson 5. Since his death, she's spoken glowingly about the man and his talents, but prior to his death, she told TV Guide in 2003 that she thought "the guy was nuts" to keep his baby rolled up in a blanket. Big turn off for it from the sounds of it.
19 Dated - Tatum O'Neal
Michael Jackson's first publicly documented relationship was with Oscar winner Tatum O'Neal. They became friends when she was 12 and he was 17 and soon after, a relationship blossomed. In a 1982 edition of Jet Magazine, he said that their love had "cooled off" and they ultimately decided to be just friends.
18 No Chance - Kim Kardashian
A little known fact about Kim Kardashian is that her first boyfriend was Michael Jackson's nephew, TJ. She was her very first love and by association, she befriended Michael. Moving on from a nephew to an uncle would be a weird, impossible transition, even for Kim Kardashian. Safe to say MJ would have no chance if he tried.
17 Dated - Brooke Shields
Michael Jackson met Brooke Shields at the 1981 Academy Awards and they quickly grew a liking to each other, going on to date for several years. There was even a point where they considered marriage, but Shields was never as enthused at the prospect. "You have me for the rest of your life, you don’t need to marry me," she recalls telling MJ in a 2009 Rolling Stone interview.
16 No Chance - JK Rowling
This one seems a little random on the surface, but trust us, Michael Jackson and J.K. Rowling are related more clearly than you might think. In a 2015 interview with Oprah Winfrey, Rowling revealed that MJ approached her about a Harry Potter musical spinoff. Not easily charmed by MJ's, well, charm, she declined the offer.
15 Dated - Tatiana Thumbtzen
Tatiana Thumbtzen is the woman who Michael Jackson featured prominently in his "The Way You Make Me Feel" music video, but Thumbtzen has since suggested that their partnership went far beyond the video. She's recalled since that they shared a passionate chemistry when he brought her on tour to perform, but when the tour was over, so was whatever they had together.
14 No Chance - Elizabeth Taylor
Michael Jackson was also closely linked to Elizabeth Taylor and they were viewed as the best of friends. He admitted to Contact Music that he did wish for more, but he worried that the media would poke fun of them as "the odd couple" because they were 27 years apart in age. "It would turn into a circus and that's the pain of it all," he added.
13 Dated - Diana Ross
In Michael's brother's - Jermaine Jackson - book You Are Not Alone, he spoke in depth about Michael's on-and-off relationship with Diana Ross. He said his brother openly referred to Ross as his girlfriend and wouldn't let anyone else near her. He even considered marrying her despite the 15 year age gap. Alas, it was the age gap that turned Ross off from marrying Michael.
12 No Chance - Sheryl Crow
Prior to gaining some singles fame of her own, Sheryl Crow was a backup dancer for Michael Jackson. She recalled her experiences to The Telegraph earlier this year and said she saw some "really strange things" backstage. She failed to elaborate, but we'd guess they were strange enough to keep her from dating the man.
11 Dated - Stephanie Mills
Stephanie Mills won awards and acclaim for playing Dorothy in the original run of The Wiz. She was replaced by Diana Ross for the movie adaptation, but as Mills explained on SiriusXM in 2015, she didn't mind because at the time, she was dating Michael Jackson, who brought her on to the set often while he filmed his scenes.
10 No Chance - Kelly Osbourne
In 2009, the world was shook by the announcement of Michael Jackson's death and several celebs spoke positive things about him. Except Kelly Osbourne, who in August of that year tweeted out "Can people just get over Michael Jackson. He's dead!" If she wasn't impressed by him after death, he probably couldn't woo her in life.
9 Dated - Madonna
The entertainment world was stunned when Michael Jackson hit the 1991 Academy Awards red carpet scene with Madonna of all people. It was all assumed that the relationship didn't move passed three dinner dates, per some friends of both parties, but in an interview with James Corden on his Carpool Karaoke, Madonna admitted she tongue kissed MJ and got him to "loosen up" with a glass of Chardonnay.
8 No Chance - Beyonce
Beyonce, in terms of sheer star power alone, is the closest person we have to star power right now. If MJ was alive today and both were neck and neck for the top spot in the music world, we'd imagine they would be super competitive with each other. That kind of competition is unhealthy for a relationship, so it just would not work out.
7 Dated - Shana Mangatal
This one is kind of in murky waters. Shana Mangatal famously grew popular after releasing a tell-all book called Michael and Me: The Untold Story of Michael Jackson's Secret Romance. It appears she divulges some private details about MJ's personal life from a 1992 affair, but has received criticism because so few credible names can co-sign her claims.
6 No Chance - Britney Spears
Among the allegations made by those who created the Leaving Neverland documentary, claims were made that MJ was "had an obsession" with Britney Spears. When Wade Robson worked as a choreographer on her first commercial tour, he recalled MJ always calling about how Spears is doing and calling her "sexy." Sounds like something Spears would get creeped out by.
5 Dated - Whitney Houston
Michael Jackson's former bodyguard Matt Fiddes visited the Today show in 2012 where he revealed that MJ had a two-week "fling" with Whitney Houston at the Neverland Ranch. She "practically" moved into the ranch and MJ even considered marrying her quickly and wished that their relationship was more than just a fling.
4 No Chance - Katie Couric
In 2013, during a visit to Howard Stern's Sirius XM show, the former Today show host revealed that 12 years prior, MJ's spiritual adviser Rabbi “Shmuley” Boteach told her that MJ was hoping to go on a dinner date with her. Because she was seeing someone at the time, she declined, though she tells Stern that she wished she accepted.
3 Dated - Lisa Marie Presley
A 16-year old MJ met the six-year-old daughter of Elvis in 1974, but a relationship hadn't begun until both were adults in 1992 following a private dinner in LA. They spoke on the phone every day from there and a proposal followed. They got married on May 26, 1994, at the Dominican Republic. They divorced in 1996 over "irreconcilable differences."
2 No Chance - Nicole Kidman
In the early 2000s, Nicole Kidman recalled to a local Australian radio station (according to femalefirst.co.uk) that she received a call from MJ's people saying that he wanted to escort her to the MTV Video Music Awards as a date. Because she never met him, Kidman thought the whole thing was "strange," and politely declined the offer.
1 Dated - Debbie Rowe
Michael Jackson originally met Debbie Rowe when she worked as an assistant for his dermatologist. A friendship blossomed and she offered to carry his child after Lisa Marie Presley refused to carry his children. After he separated from Presley, Rowe was pregnant with his child and not long after, they got married. She had two of his children before and then a third after their divorce.
Sources: ew.com, youtube.com, contactmusic.com