By September 1990, George Michael was at the top of the pop charts following the release of his sophomore solo album, Listen Without Prejudice Vol. 1, but the singer was struggling with fame.
As a new decade dawned, the former Wham! singer was trying to reinvent himself as an artist and as someone who wanted his music to speak for itself rather than promoting it. The "Heal the Pain" singer was in a bitter dispute with his label, Columbia/Epic because he did not want to promote the album and wanted to shun the public eye.
As his fame climbed, he pushed the world away, but got a letter of encouragement from a very unlikely source – legendary singer Frank Sinatra.
Michael told the Los Angeles Times in 1990 around the time the record came out: "I'm not stupid enough to think that I can deal with another 10 or 15 years of major exposure. I think that is the ultimate tragedy of fame... People who are simply out of control, who are lost. I've seen so many of them, and I don't want to be another cliche."
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As Listen Without Prejudice Vol. 1 debuted at the No. 2 position on the Billboard album chart and the album's lead single, "Praying for Time," spent two months atop the singles charts, "Old Blue Eyes" learned about the English musician's struggle with the spotlight through the Times interview and wrote to him.
"Come on, George," Sinatra wrote. "Loosen up. Swing, man. Dust off those gossamer wings and fly yourself to the moon of your choice and be grateful to carry the baggage we've all had to carry since those lean nights of sleeping on buses and helping the driver unload the instruments."
At the time, Michael did not want to go on MTV to promote his work. He refused to star in music videos, which also ended up furthering his fame as then-rising director David Fincher directed a bevy of models — including Naomi Campbell and Cindy Crawford — in the "Freedom '90" video.
The video would later be hailed as one of the best ever made.
Sinatra, then in his mid-70s, added: "The tragedy of fame is when no one shows up and you're singing to the cleaning lady in some empty joint that hasn't seen a paying customer since Saint Swithin's day. And you're nowhere near that; you're top dog on the top rung of a tall ladder called Stardom, which in Latin means thanks-to-the-fans who were there when it was lonely."
The letter appeared in the Los Angeles Times shortly after it was written and is currently published by the online museum Letters of Note.
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The New Jersey-born singer, like Michael, knew the highs and lows of celebrity and tried to warn the British pop star that he should be careful what he wishes for.
Sinatra died in 1998 of a heart attack at 82.
The "Faith" singer is believed to have died from heart failure in his home in Oxfordshire, England, on Christmas Day.
Despite the success of Listen Without Prejudice Vol 1., he and his label never put out its follow-up, Vol. 2, which was slated to hit stores in June 1991. The record has never been released.