There’s an avalanche of thoughts that tumble through one’s mind when you are left to ponder the extraordinary (yet criminally underrated) career of George Michael following his shocking death on Christmas Day at the age of 53. But for this writer, the date of January 30, 1989, remains a moment that underlines the sheer gift, curse and deeply complex appeal of the ultimate white rhythm and blues vocalist. It was at Los Angeles’s Shrine Auditorium during the American Music Awards where Michael stepped on a debate-igniting, cultural land mine.

The former member of the monstrous pop duo Wham! was coming off the unfathomable commercial triumph of his critically-acclaimed solo debut Faith, which would go on to sell 25 million copies worldwide (10 million in the U.S. alone). Michael was now being viewed as a worthy addition to the ‘80s holy pop trinity of Michael Jackson, Prince and Madonna. When you headline your own sold-out world tour (The 1988 Faith trek became the second-highest-grossing tour of that year, pulling in nearly $20 million), fire off six consecutive top five singles on the Billboard charts (fueled by the one-two punch of the No. 1 rockabilly-dipped-in-soul title track and the dark, controlling church-infused ballad “Father Figure”) and win Album of the Year at the Grammys, you can pretty much write your own check.  

But before that coronation solidified his place as a legit music industry behemoth, Michael found himself at the center of a racial tsunami when he won two AMAs for Favorite Album (Soul/R&B) and Favorite Male Artist (Soul/R&B). This was the era of the “Crossover Negro,” especially in the recording biz, as the aforementioned King of Pop and The Purple One — alongside the likes of Whitney Houston, Janet Jackson, Tina Turner, and Lionel Richie — all took turns ruling the top of the charts. Teddy Riley was leading the multi-platinum New Jack Swing wave. And hip-hop’s golden age was just kicking off, forcing MTV to create Yo! MTV Raps just to keep up with the street-infused genre’s groundbreaking stars like N.W.A., Public Enemy, Eric B & Rakim, Salt-N-Pepa and De La Soul. Black culture was cool and was only going to get cooler in the next decade.

So, needless to say, there was plenty of shade thrown when George Michael beat out both Michael Jackson and Bobby Brown (!!!). Leading the dissent was outspoken film director Spike Lee, who balked at the idea of any Caucasian vocalist picking up such honors when R&B favorites like Luther Vandross and Anita Baker were all but ignored by white pop radio stations. On the B-side to PE’s landmark, incendiary 1989 anthem “Fight the Power,” Lee immortalized his beef: “Flav, I was watching the American Music Awards…what is George Michael doing there?” the groundbreaking auteur quipped to Public Enemy’s Flavor Flav. “How’d he win all the awards? How’d he win the R&B category?”  

A respectful Michael did not balk at any of the criticism. “I’m not going to pretend I wasn’t happy to get them,” he admitted to a reporter. “But I do understand the argument that says this guy is just an acceptable version of Black music for white America.”

However, looking back at the entire brief blowup, Michael’s deep connection with Black music fans made his somewhat eyebrow-raising wins less offensive than say, Macklemore leapfrogging Kendrick Lamar at the 2014 Grammys for Best Rap Album. For many African-American followers, their first introduction to the East Finchley, London, native was Wham!’s 1982 cheeky, disco-rap rave-up “Young Guns (Go For It).” Michael and his conspicuously silent partner Andrew Ridgeley were pushed as cutesy teen idols that indulged in the funk.

But while Wham!’s No. 1 commercial breakthrough, 1984’s overtly day-glow single “Wake Me Up Before You Go-Go,” made them global stars, it was a heaven-sent slow jam that forever gave Michael his ‘hood pass. At just 17 years old, the gifted singer/songwriter wrote and produced the mournful torch song “Careless Whisper,” a mammoth hit that not only reached No. 1 on the Billboard Hot 100, but also became a top 10 hit on the U.S. Hot Black Singles, earning its place as a quiet storm staple on R&B radio. “I’m never going to dance again/Guilty feet have got no rhythm,” remains one of that era’s most heartbreaking lines ever recorded. This was a different cat.

The dance floor burner "Everything She Wants" became a karaoke/shower/road trip favorite ‘round the way. Michael was a legit pop icon who was embraced by Black folk because we recognized real. He transcended generic and truly tired "blue-eyed soul" labels. Michael’s “Blackness” all seemed so innate. Faith entered the top 10 R&B/Hip-Hop Albums chart at No. 1. If you were an African-American kid in late ’89, having a George Michael album in your collection next to such noteworthy R&B releases by Guy, Babyface and Janet was not at all uncommon.

The burgeoning talent didn’t have to attain a co-sign by hooking up with the popular Black producer of the day as Justin Timberlake did when he hit the studio with Pharrell Williams. And Michael never pulled a Pink, chasing the pop-rock brass ring after using African-American culture as a mere stepping stone. For Black girls, he was the ultimate go-to white-boy crush. Michael’s chiseled, male model looks made him a dreamy sex symbol throughout the world. Never mind that he was privately living as a gay man, a truth that he finally publicly embraced after he was forced to come out following an April 1998 arrest when Michael was caught engaging in a sexual act by an undercover cop in a Beverly Hills public toilet.

But even throughout all the singer’s turbulent ups and downs, George Michael displayed the kind of soulful, effortless vocal range and class that gave him ample room to go from a gutsy 1987 duet with Queen of Soul Aretha Franklin on “I Knew You Were Waiting (For Me)” to literally filling the larger-than-life shoes of Queen’s late AIDS-stricken frontman Freddie Mercury during a show-stealing moment at a 1992 tribute show. George Michael was magic. That much was clear.

Indeed, like other white performers who were genuinely comfortable on the other side of the tracks (Dusty Springfield, Elton John, Bobby Caldwell, Teena Marie and Amy Winehouse), Michael championed the African-American artists that he openly obsessed over. Rather than simply cover an automatic lay-up like Stevie Wonder’s "Lately," he dug deep for the obscure album cut from the master with "They Won't Go When I Go.” On and offstage, he could hold his own against his heroes and contemporaries: Smokey Robinson, Whitney Houston and Mary J. Blige.

Michael continuously challenged himself as an artist. 1990’s Listen Without Prejudice Vol 1 is miles ahead artistically from any of his previous recorded outings. Pop stars weren’t supposed to make synth-driven jazz records like “Cowboys and Angels,” centering on a tragic love triangle (Michael was secretly in love with a man while a female friend pined away for the singer). The heartbreak of that composition is eerily palpable: “I know you think that you're safe Mister/Harmless deception/That keeps love at bay/It's the ones who resist that we most want to kiss/Wouldn't you say?”

But Michael routinely stepped outside his comfort zone. He followed Prince’s lead, suing his longtime label home Sony over what he viewed as a lack of artistic freedom. Michael’s immense vocal chops still shined, even on the dwindling record sales of Older (1996), Songs From the Last Century (1999), Patience (2004) and Symphonica (2014), a release culled from his acclaimed live tour of the same name.  

Yes, George Michael deserved to be taken more seriously as a first-rate songwriter. There was always the lingering temptation by some onlookers to dwell on the singer’s good looks. But Michael understood that you could only go so far with a pretty face. He had loftier ambitions: SOUL MAN.