David Gray / Reuters

George Michael was already a big star by the time I was developing musical tastes. I knew I liked his music; my sister had introduced me to “Wake Me Up Before You Go-Go,” and the many hit singles from Faith had already entered that rarefied sphere of cultural ubiquity that ensures their longevity in the karaoke songbook.

But he was an unusually self-referential star, and that made becoming a George Michael fan into something of a project. He had the habit of titling his songs and albums with numbers, as though he were Wagner composing the Ring Cycle, making some sort of never-ending symphony. Even a danceable bauble like “I Want Your Sex” unfolded in three parts. The title of Listen Without Prejudice, Vol. 1, one of the first albums I owned, cruelly teased my appetite for a sequel that never came. And then there was the puzzle that was “Freedom! ’90."

The video for “Freedom! ’90,” directed by David Fincher, was inescapable during my tween years. Famously, Michael himself was barely in it; instead, a parade of supermodels—and a random, shapely, half-naked man hanging from his gravity boots—lip-synch the lyrics to the song as icons of his earlier stardom (a leather jacket, a jukebox, a guitar) spontaneously combust.

It wasn’t hard to infer from the song that Michael was making some sort of layered statement about his celebrity, but as a kid in the days before Google, it was difficult to parse the meaning of that statement. The year suggested in the song’s title felt like a clue to the song’s deeper meaning, to Michael himself, and perhaps to larger mysteries I could only guess at.

Older fans of George Michael already knew the fact I discovered as I was unraveling this mystery as a kid, that “Freedom ’90” was Michael’s second song called “Freedom.” The first—recorded with Andrew Ridgeley while he was a member of Wham!—is now fairly described as a deep cut, unmentioned in every karaoke songbook I’ve seen. It’s not hard to tell, though, why it was once a modest hit, with its simple, buoyant melody, ’80s-friendly “doo-doo-doos,” and its teen-candy message of eternal devotion in the face of heartbreak. The refrain:

I don't want your freedom
I don't want to play around
I don't want nobody baby
Part-time love just brings me down
I don't need your freedom
Girl, all I want right now is you

“Freedom” exerted an unusual pull over Michael’s later work. He revisited the song again and again in the first decade of his solo career. Each time, he tears apart a different piece of the song’s message, exposing it as a lie. The chorus of “Freedom” is what you hear on the church organ that introduces “Faith.” For fans of Wham!, the reference probably felt like a wink: This may be the new me, but don’t worry, I’m still making toe-tapping tunes about love. But the meaning of the two songs couldn’t be more different: While “Freedom” is about a kid swearing his undying fealty to an unfaithful lover, “Faith” is the story of a grown-ass man kicking his ex to the curb despite the ex’s pleas to stay.

Then, of course, there’s “Freedom ’90,” the funkiest song on an album filled with plaintive ballads about war and pain. No more coded messages about lovers and exes. In the song, Michael is himself, an artist speaking directly to his fans about the lie of fame, promising to no longer play by its rules. It sounds almost like a coming-out anthem: “I think there’s something you should know / I think it’s time I told you so / There’s something deep inside of me / There’s someone else I’ve got to be.”

When he did come out in public, shortly after having been arrested for lewd behavior in a public restroom, eight years after “Freedom ’90,” Michael said his sexuality was an enigma, even to him, but his music was always honest. “The songs that I wrote when I was with women were really about women, and the songs that I’ve written since have been fairly obviously about men,” he said. “So I think in terms of my work, I’ve never been reticent in terms of defining my sexuality.”

That was the year I graduated from high school, and I remember two conflicting emotions: vicarious pride that a sex symbol like George Michael could be out and public about being gay, and fear that his coming out would mean the end of his career, a warning shot to men like me.

Instead, six months after he came out, he released “Outside,” the brazen, cheeky lead single on his greatest-hits compilation, coyly titled Ladies & Gentlemen: The Best of George Michael. It was neither his best song nor an enduring chart-topper, but it got plenty of radio play, and the album sold well. In one stroke, he reminded the world of his immense musical talent, and proved that his brilliance and sex appeal could still move records even after he discarded his teen idol image, and even after the world knew he was gay. Three years later, I started coming out myself.

George Michael may have died too young, but he also managed to live, true to himself as an artist and as a gay man. His example helped inspire me and others to claim a piece of that freedom for ourselves. Now, he’s experiencing a posthumous coming-out as a secret philanthropist. “I won’t let you down, so please don’t give me up,” he pleaded in “Freedom ’90.” Oh, George. Then or now, you never needed to worry about that.

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