Remembering Frank Sinatra’s letter to George Michael: “Loosen up. Swing, man.”

Popular culture has been graced with many great performers over the years. Two of the most iconic, who need no real introduction, are Frank Sinatra and George Michael.

They might represent different eras and have distinct music styles, but ‘Ol’ Blue Eyes’ and the Wham! leader are connected in that they were generation-defining musicians, masters of stagecraft and tremendous personalities, three aspects that they used to change the world. Their standings would also see them converge in the most remarkable of ways.

In 1990, 27-year-old George Michael had experienced the intense trappings of fame as the leader of Wham! and as a solo artist for years. Despite being still so young, the musician expressed his yearning to escape the spotlight when speaking to Los Angeles Times’ Calendar MagazineDescribed as the “reluctant pop star” in the article’s headline, this was one of the most significant moments where Michael outlined his discomfort at his position.

“It’s quite simple, really,” the English musician explained. “I decided that the thing I really enjoy … the thing I really needed was my songwriting. I didn’t need the celebrity.” Following this agreeable point, Michael outlined how miserable his fame made him and his desire to never feel like that again. Unfortunately, this would never come to fruition. His coming brushes with the invasive side of the media in the decade were to be some of the most difficult of his life.

Michael would also deal with those instances with comic brilliance, and further cement his status as a cultural legend by doing so. Yet, in 1990, they were still a long way off. His comments to Calendar weren’t entirely adored though and prompted a response from the elderly Frank Sinatra, who was in his seventh decade on the planet. Displaying the unfettered grace that made him such a hero, Sinatra sent a written response to Michael, imploring him to carry on, which was published by the same newspaper. It makes for compelling reading, reflecting how Sinatra had his finger on the pulse right to the end.

He wrote: “Dear Friends, When I saw your Calendar cover today about George Michael, ‘the reluctant pop star,’ my first reaction was he should thank the good Lord every morning when he wakes up to have all that he has., And that’ll make two of us thanking God every morning for all that we have.”

He continued: “I don’t understand a guy who lives ‘in hopes of reducing the strain of his celebrity status.’ Here’s a kid who ‘wanted to be a pop star since I was about seven years old.’ And now that he’s a smash performer and songwriter at 27 he wants to quit doing what tons of gifted youngsters all over the world would shoot grandma for – just one crack at what he’s complaining about.”

“Come on George, 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.”

“And no more of that talk about ‘the tragedy of fame.’ 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 swing master concluded: “Talent must not be wasted. Those who have it – and you obviously do or today’s Calendar cover article would have been about Rudy Vallee – those who have talent must hug it, embrace it, nurture it and share it lest it be taken away from you as fast as it was loaned to you. Trust me. I’ve been there.”

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