George Michael, who passed away over the weekend at the age of 53, was a pop star who could only have been incubated during the 1980s. The mix of ideas and institutions that were in the process of figuring themselves out during that chaotic decade—MTV, gay rights, the function of pop stars in an increasingly celebrity-soaked culture—all became intrinsic to Michael’s cross-generational, cross-demographic appeal, igniting his songs and helping to solidify him as an icon.

Wham!, Michael’s duo with his school pal Andrew Ridgeley, released its first album, the fizzy Fantastic, in 1983. The prejudices of the era—particularly the ones that automatically looked down on music that appealed to young women, and music made by those acts whose telegenic nature proved to be a big hit on the then-nascent MTV—led people to write off Wham! at first, although certain savvy observers latched on to Michael’s talent early. Writing in the British pop magazine Smash Hits, future Pet Shop Boy Neil Tennant praised Wham!’s early single, “Wham Rap,” as “one of the most striking dance records of the year” and remarked on Michael’s confidence. Legendary Radio 1 DJ John Peel, after spinning the bouncy “Young Guns (Go For It),” admonished any potential critics with a witchy warning: “The first person to write in and say, ‘You shouldn’t have played that—you should have played the [British punk pioneers] UK Subs instead,’ will be turned into a toad.”

Make It Big, the album that followed in 1984, blew Wham! up across the pond, with the playful “Wake Me Up Before You Go-Go” blanketing MTV and causing a run on CHOOSE LIFE t-shirts. The pump was primed for Michael to break out early. When “Careless Whisper,” the sax-tinged ballad that showcased Michael’s torch-singer side, was released in the U.S., it was credited to “Wham! featuring George Michael.” Still, the pair soldiered on until 1986, releasing more singles both as a pair (including the glorious “Freedom,” the clarion melody of which would become a motif in later songs) and with Michael top-billed (the wounded “A Different Corner,” which trafficked in winter-like motifs that recalled the duo’s eventual Yuletide standard “Last Christmas”).

His solo debut Faith landed with thunderbolt-like intensity, Michael as auteur who flaunted his smoldering sexuality and in-depth knowledge of R&B. The record fluidly shifted gears between the title track’s flinty proto-rock and the anxious balladry of “Father Figure,” not to mention its use of the dance floor as an escape valve on “Hard Day,” or its taking stock of a world on the edge on the aqueous “Hand To Mouth.” And the tortured, questioning “One More Try” was one of Michael’s singles to top both the Hot 100 and the Hot Black Singles chart in 1988.

That year, just as Faith was asserting its supremacy on the pop charts, he told Rolling Stone: “If you listen to a Supremes record or a Beatles record, which were made in the days when pop was accepted as an art of sorts, how can you not realize that the elation of a good pop record is an art form? Somewhere along the way, pop lost all its respect. And I think I kind of stubbornly stick up for all of that.”

Michael’s career was studded with proof of his deep respect for the art of pop. There were the covers, which never Xeroxed the originals. His loving version of The Doobie Brothers’ “What A Fool Believes” leaned into its soulful lamentation; he turned Wham!’s version of The Isley Brothers’ “If You Were There” into a showcase for his pleasure-in-pain vocal; and he offered a guided tour of the previous 100 years of pop, from “Brother, Can You Spare A Dime?” to “Roxanne,” on his 1999 album Songs From The Last Century. He held his own with Queen on the soaring “Somebody To Love,” and he imbued Stevie Wonder’s “Love’s In Need Of Love Today” with even more heart while performing alongside the legend.

And then there were the sly nods to his forebears. The sinewy “Fastlove” draws Patrice Rushen’s “Forget-Me-Nots” into its orbit. “Waiting For That Day” takes the Rolling Stones’ “You Can’t Always Get What You Want” under its wing, turning the Stones’ sardonic track into words of comfort. His fiery mashing up of the acid house producer Adamski’s stinging “Killer” and The Temptations’ defiantly bereft “Papa Was A Rolling Stone” bridged generational gaps. And “Freedom ’90,” his anthem of liberation from pop music’s systems that became the signature offering from his second solo album, Listen Without Prejudice Vol. 1, echoes the 1984 Wham! track its title pays homage to, its triumphant chorus sounding like an older, wiser countermelody to its antecedent.

After Listen came out, the ’90s were rough on Michael. In 1992 he sued to be released from his eight-album contract with Sony Entertainment, saying that the conglomerate had soft-sold Prejudice. A British judge ruled against him in 1994, calling the contract “reasonable and fair” and, most importantly, comprehensible to Michael. In 1993, his lover Anselmo Feleppa passed away from an AIDS-related brain hemorrhage. In 1997, his mother died, resulting in what Michael described to Oprah Winfrey as “the blackest period of my life, really.” Michael was also still in the closet and would be until 1998, when his arrest for soliciting sex in a Beverly Hills park restroom led to him coming out.

Older, which came out in 1996, was dedicated to Feleppa. Compositions like the tense “Spinning The Wheel” exhibited Michael’s newfound influences. He further showed off his deftness with ballads through the bossa nova-tinged tribute to Feleppa “Jesus To A Child,” and a pillowy cover of Bonnie Raitt’s lament “I Can’t Make You Love Me.” In 2004, he released what would be his final album, Patience. It has a relative stillness to it, with Michael’s still-formidable instrument taking center stage amidst booming house beats (“Precious Box”) and razor-sharp indictments of the War in Iraq (“Shoot The Dog”).

George Michael’s political side rounded out the deeply felt emotion in his songs. Tales of his immense charity that have cropped up in the wake of his passing, from his donations to people he encountered to his unfailing support of British nurses, transform lyrics to songs like the searching “Praying For Time” into actions. And his post-coming-out stand against the homophobic tendencies of the press—particularly the tabloids in his home country of Britain, who loved to speculate on his love life even after he became involved with art dealer Kenny Goss—was an extension of the matter-of-fact attitude he had toward sexuality even in his closeted “I Want Your Sex” days. The winking video for his disco fantasia “Outside,” which satirized the situation that got him on the cover of the tabloids, was an extension of his general attitude toward homophobes: “The bastards will get you in the end, baby,” he told The Advocate in 2000. “So don’t give them that power. Be proud of who you are and deal with the shit.”

Michael’s meticulous work rate and fluctuating health—he was rushed to a Vienna hospital in 2011 with pneumonia and upon release he thanked the doctors who spent “three weeks basically keeping [him] alive”—meant that his only releases after Patience were occasional singles and the live collection Symphonica, which chronicled his 2011-12 tour where he fronted an orchestra. His legacy still loomed large, though. This year’s Key & Peele buddy comedy Keanu hinged on a deep appreciation of his catalog. “Last Christmas” is one of the premier entrants in the new Yuletide canon. And his 2011 appearance alongside James Corden on the UK telethon Comic Relief essentially launched “Carpool Karaoke,” which this year made the leap from Late Late Show segment to standalone show.

The sterling combination of Michael’s voice and his deep respect for pop as not just an art form, but as a way to bring people up together, created songs that will be sung along with, cried to and used in romance’s fluctuating times. People will still be singing along with his biggest hits long after Michael’s too-early death.

His “Freedom ’90” exhortation that he’d “really, really, really love to stick around” will just have a bittersweet aftertaste now.

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