999,821: George Michael & Aretha Franklin - I Knew You Were Waiting (For Me)

George Michael had everything going for him in the late ‘80s. A teen idol just a couple short years before, Michael’s blazing solo success had him positioned as the heir apparent to Michael Jackson, Prince, and Madonna. Sadly, Michael was never able to escape his bubblegum past with Wham! – at least not in his own mind, where he constantly felt the need to prove he was something MORE than whatever he was at the moment. As such, Michael wound up rivaling Axl Rose as the late-‘80s superstar whose inferiority complex most effectively sabotaged the brilliance that made him a star in the first place.

And make no mistake, George Michael was brilliant. Until Amy Winehouse came along two decades later, Michael ranked as the last great blue-eyed soul singer, and the last to truly cross over between white and black audiences. Why was he able to do that? Well, he could write a great pop song, but more importantly, that motherfucker could flat-out SING. He knew it, but despite “Careless Whisper,” the world didn’t realize it, since Wham! wasn’t exactly perceived as musically substantive. So what’s a closeted British white boy with a killer set of pipes to do?

Enter Aretha Franklin, coming off a mid-‘80s comeback with hits like “Freeway of Love” and “Who’s Zoomin’ Who.” Routinely ranked among the greatest soul singers of all time for her combination of vocal power and technique, Aretha had also become a feminist icon thanks to her opposite-sex recasting of Otis Redding’s “Respect.” Franklin is so widely revered, white-girl lesbian sex guru Susie Bright even named her daughter Aretha in tribute. NOBODY questions Aretha Franklin’s credentials.

And this is what made George and Aretha’s chart-topping ’87 duet “I Knew You Were Waiting (For Me)” so revelatory. That’s Aretha Franklin…and that’s George Michael??? Going toe to toe? George Michael? That guy in the “Choose Life” shirt who was just making junior high girls wet their pants with that goddamn jitterbug song? Holding his own right next to Aretha Fucking Franklin?! No way. No way, brah. Uh-uh.

Now, it isn’t as though Michael comes out on top here, or even registers as an equal. The point here is like the point of the first Rocky movie – the underdog doesn’t win, but against an unbeatable opponent, he holds his own. You can almost hear Michael’s confidence building as the song goes along. In the first verse, he’s quiet and breathy, as if he wants to play Franklin’s opposite so he can’t be compared on the same terms and found wanting. Then he starts to let loose a little at the end of the second verse. By the end of the song, he and Franklin are trading off vocal lines over the chorus like it ain’t no thang. Even if he lacks Franklin’s raw gospel power, the supple elasticity and natural sob in Michael’s voice has become more and more apparent. This coming-out (ha!) party was the stepping stone to Faith, which deserves to be mentioned with Thriller, Purple Rain, and Born in the U.S.A. as one of the great blockbuster pop albums of the ‘80s.

Sadly, the mature, emotionally complex love songs that made Faith such a rewarding – and substantive! – work weren’t enough for Michael. On his next album, Listen Without Prejudice, Vol. 1, Michael fell victim to that great bugaboo of Reagan-era popular music, the incessant rock-critic demands for socially conscious material criticizing the status quo. Michael took apart the superficiality of his own appeal on “Freedom ’90,” and for the next two decades disappeared up his own ass, crafting intermittent albums of dour, self-consciously serious songs that were intentionally not as catchy or immediate, whittling down his audience in the manner of Pearl Jam so that his self-image as a Serious Artist would never again come into conflict with the reality that he was superbly talented at making mainstream music. By now, Michael could have taken his rightful place as a gay pop icon to rival Sir Elton John. Yet, sadly, the fun of blowing dudes in public restrooms never again found its way into the music he made, constituting an enormous waste of talent to rival…well, the aforementioned Guns N’ Roses and Amy Winehouse.

I Knew You Were Waiting (For M...