George Michael had two strong recurring premonitions. The first was that he'd be famous. The second was that he'd die young.
"From a really early age, I believed I was going to be a star," he told me when I interviewed him at length in 1986. "I remember being on a bus when I was a child, about 8 or 9. I'd had a bad day at school -- I'd been picked on -- and I remember thinking it would be OK when I was older, because I wasn't going to be like everybody else. That's the reason kids want to be stars. They think they'll be able to rise above their problems because they're famous -- which obviously isn't true."
Michael, who died at home in Oxfordshire, England, at the age of 53 on Christmas Day, had enduring faith in his talent. But one of the most striking things about him was the discrepancy between the poised, clever sex symbol I was talking to and his accounts of growing up outside London. "People have no comprehension of what I looked like as a kid," he said, laughing. "I was such an ugly little bastard."
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Even when fans were swooning over him, he remembered being an overweight kid who wore glasses. "He never thought he was good-looking," Rob Kahane tells Billboard. Kahane managed the singer at the height of his solo stardom. "When he looked in the mirror, he'd still see a pudgy, homely kid."
Like a lot of disenchanted preteens, Michael took solace in the escapism of pop music, and he obsessively studied how hit songs were arranged. He loved pop so dearly, he turned himself into its embodiment, and an unashamed advocate of its merits. "You either see pop music as a contemporary art form or you don't," he said. "I do, very strongly. It's the only day-to-day, moving art form."
Wham!, the duo he formed with childhood friend Andrew Ridgeley, was outrageously, blindingly pop: Their hits had quick tempos, upbeat hooks and peppy videos of the duo, often in shorts or cropped T-shirts. Michael once described them as "f---off pop songs people can't resist."
Wham! had everything but respect -- one writer called them "two unsophisticated con men" -- so Michael split from Ridgeley. He dueted with Aretha Franklin and Stevie Wonder. He wrote, arranged and produced 1987's Faith; the album sold 25 million copies worldwide and 10 million in the United States, where four of its singles went to No. 1 on the Billboard Hot 100, leading to a Grammy for album of the year. Michael, certain he would lose to Tracy Chapman or Sting, didn't attend. (Kahane, who teased the singer like he was a little brother, called him and said, "Listen, idiot, you won.") Michael made all the music decisions, and all the business decisions, too. "Being a control freak is f--ing exhausting," he told me. "It took me about two months to suss out that the music business was full of assholes, and I knew better than they did. That's when I dug my heels in."
How stars reacted to George Michael's death:
A lot of heel-digging followed. By the time Faith started to fade, "I felt like I was going insane," he later said. Michael thought his renown as a sex symbol stopped people from giving his music the respect it deserved. So in 1990, before he released Listen Without Prejudice Vol. 1, he planned a severe change: no interviews, no tours and no appearances in his own videos. In the famous clip for "Freedom! '90," starring five supermodels, Michael literally destroyed a guitar, jukebox and leather jacket, each a key element of his "Faith" video. "George was a very difficult person to manage -- not because of his personality but because of his belief system," says Kahane.
Kahane hated Michael's plan, but Michael's U.S. label hated it more. Don Ienner, who was president of Columbia Records, explains: "Clearly, I was concerned that George didn't want to promote the album, tour behind it or star in his own videos, all of which had made him, deservedly, one of the most important stars in the world. If that was his vision, then we'd support it, but I thought there was a more elegant way to quiet the frenzy that was making him uncomfortable. Why announce that he wasn't supporting the album, instead of being quiet and letting the music speak for itself? And when he blew up the guitar, the jukebox and the jacket, I felt it could offend fans who loved those images."
At one point, according to subsequent court testimony, Michael overheard an argument between Kahane and Ienner, who allegedly referred to the singer as "that faggot client of yours." ("It's a silly accusation, and it's untrue," Ienner told me.)
"That was the trigger that set George off," says Kahane. The singer went to court to dissolve his contract, which he ridiculously likened to slavery. "It was a moral issue," he later said. He lost the lawsuit, which cost him about 30 million British pounds and kept him away from recording and touring for three years. "He was stubborn," adds Kahane. "But that's also why he performed at so many benefits — he had principles."
In the midst of the Sony lawsuit, Michael's partner of two years, Anselmo Feleppa, died of an AIDS-related brain hemorrhage. "When he lost Anselmo, I thought he was going to do something bad to himself. I had people stay with him," says Kahane. Michael came out to his family. Soon after, his mother, with whom he was very close, told him she had terminal cancer.
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Michael later said he was clinically depressed during that period. Sometimes Kahane's sister would read the singer's tarot cards. "He was obsessed with saying, 'I know I'm going to die young,'" recalls Kahane. "He'd say, 'It's OK. I've had a great life.'"
DreamWorks Records paid a hefty fee to buy his contract from Sony, and he released Older in 1996. It sold well worldwide but flopped in the United States. "George delivered us a completely finished album package, which is unusual. He understood how to use videos and photos in a way few people did," says Robin Sloane, head of creative services at Geffen Records. But the images he picked were "somber, moody, mournful. It was over the heads of MTV viewers. People wanted the other George Michael."
In 1998, he was arrested for "engaging in a lewd act" with an undercover policeman in a Beverly Hills park. Michael felt his fans already understood that he was gay. "He said it was everywhere in his lyrics," recalls Bryn Bridenthal, who was head of publicity at Geffen. But he agreed to an interview on CNN so he could come out formally. "He had a sense of humor about it and wasn't defensive. He did charming really well," says Bridenthal.
Unlike his contemporaries -- Michael Jackson, Madonna, even Prince, to an extent -- Michael stopped trying to make hits. He released only two albums in his final 20 years: an album of mostly standards, sung with an orchestra, in 1999, and 2004's Patience, on Sony Music, where again he worked with Ienner, who was now chairman and CEO. Michael's music was chilly, thoughtful and rarely celebratory. When he made headlines in the last 10 years, it was for personal problems: a near-fatal case of pneumonia that forced him to cancel a 2011 tour of Europe, or drug arrests, or a car accident while driving under the influence, which led to a four-week jail stint.
In early December 2016, when Kahane was in London, a mutual friend encouraged him to reach out to Michael, who had recently finished 18 months in a Swiss rehab facility. "I called him, and he said, 'I'm good.' He sounded fine," says Kahane. Though the two hadn't talked in years, they made a plan to have lunch in January. And Kahane heard a few of Michael's new songs, which he says are "totally pop, like something that would've been on Faith. The songs weren't depressing. That's why I thought everything was OK with him."
Michael was intermittently active on Twitter, and in April 2014 he told fans he'd been watching video of his 2011 tour. "I saw the luckiest man on earth. So much love given to one man," he wrote. "If only I had known, way back then, I'd have been one seriously happy kid. I love you."