DIANA ROSSRoss
first got a glimpse of Jackson's talent when she watched him and his older brothers perform at Motown head Berry Gordy's Detroit mansion. Jackson, then 10, even lived with his Supreme mentor, whom he once said he confided his "deepest, darkest secrets." More than a decade later, the pair starred in 1978's The Wiz, an all-black version of The Wizard of Oz.
Through all the child molestation allegations Jackson faced, he had the staunchest support from his longtime friend Dame Elizabeth Taylor, who the singer told Oprah Winfrey in 1993 was the one who anointed him the King of Pop – a moniker that stuck. What bonded the seemingly mismatched pair? Taylor told Larry King in a 2006 interview that "both had horrible childhoods."
DEBBIE ROWE
Who in the world is Debbie Rowe? The world found out in November 1996 when Jackson and the 37-year-old assistant to the singer's dermatologist confirmed news that they were expecting a baby together. Ten days after learning he was going to be a dad, the King of Pop married his 6-months-pregnant companion in a civil ceremony Down Under.
LIZA MINNELLI
Longtime friends (photographed together at a party in 1982), Jackson made a love connection for pal Minnelli, introducing her to her fourth husband, David Gest, at his 30th Anniversary Concert Celebration in 2001. Minnelli repaid the gesture by having the singer serve as a co-best man and ring bearer at her star-studded 2002 wedding to Gest.
MACAULAY CULKIN
A frequent guest at Jackson's Neverland Ranch as a young child, Culkin struck up a friendship with Jackson after appearing in his "Black or White" music video. In 2005, Culkin took the stand in the pop star's molestation trial where he testified that the singer never molested him as a child, calling the allegations "absolutely ridiculous."
TATUM O'NEAL
Though they disputed the nature of their relationship, this much is true: O'Neal (pictured with Jackson in 1979) met the singer at an L.A. club when she was 12 and he was 17, according to her book A Paper Life. The two developed a friendship, talked frequently and, reportedly, shared a kiss at her home. Jackson later described in ABC's Living with Michael Jackson documentary that O'Neal attempted to seduce him, which she denied.
CHER
Cher and Jackson maintained a connection over the decades after the pop star appeared on The Sonny & Cher Comedy Hour with his older brothers as part of the Jackson 5. In recent years, Cher (photographed with Jackson at a Dreamgirls opening party in 1983) grew critical of the singer, especially as a parent. She told TV Guide in '03, "I cannot imagine putting my children what he put his children through."
BROOKE SHIELDS
Linked in the '80s (and photographed with Emmanuel Lewis at a Grammy party in 1984), Jackson once told Oprah Winfrey about their relationship: "We try not to be everywhere, go everywhere. It's mostly at home. She'll come over. I'll go to her house because I don't like going out in public."
MADONNA.
Talk about stealing the show: Jackson took the Material Girl as his date to the 1991 Oscars, creating a worldwide paparazzi frenzy. Madonna, decked out in a Bob Mackie gown and $20 million in diamonds, found her match in Jacko, who stepped out in gold-tipped cowboy boots, a diamond brooch and not one, but two gloves for the starry occasion. The two went on to reportedly collaborate on a song for Jackson's Dangerous album.
