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.”