In The Number Ones, I’m reviewing every single #1 single in the history of the Billboard Hot 100, starting with the chart’s beginning, in 1958, and working my way up into the present.
“I’m not planning on going solo.” George Michael sang those words on “Wake Me Up Before You Go-Go,” the song that made Wham! pop stars in the US. And then Michael immediately went solo. Kind of. Mostly.
The billing of “Careless Whisper” is a curious thing. You could argue that Wham! was already pretty much a George Michael solo project by 1985. Michael was Wham!’s lead singer, songwriter, and producer. He was the face of the group, the one who was the clear focus of all the videos. Andrew Ridgely, Michael’s childhood friend and Wham! partner, had been instrumental in helping to come up with the group’s image, and he’d co-written the early UK hits “Wham Rap! (Enjoy What You Do)” and “Club Tropicana.” But by the time Wham! released their second album Make It Big, Ridgely was mostly just the guy who danced behind George Michael in the videos.
But “Careless Whisper,” the last song on Make It Big, is actually the only song on the album that Ridgely co-wrote. That makes it the least solo song on the album. In most of the world, “Careless Whisper” was sold as a George Michael solo single, even though it was on the Wham! album. In the US, though, Epic billed “Careless Whisper” as a song from “Wham! Featuring George Michael.” With the exclamation point, that becomes an even more confusing syntactic jumble. Wham! already featured George Michael. It’s like saying “Eurythmics Featuring Annie Lennox” or “Simon And Garfunkel Featuring Paul Simon.” It just doesn’t make any sense. But Billboard eventually named “Careless Whisper” the #1 single of 1985, so apparently it worked.
George Michael started writing “Careless Whisper” before Wham! even had a name. He came up with the basic idea when he was 17, working as an usher in a movie theater. Michael riding a bus to his job when he thought up the sax riff. Ridgely wrote the song’s chord progression, and the two of them recorded a demo for the single at Ridgely’s parents’ house. Along with “Wham Rap!” and “Club Tropicana,” “Careless Whisper” was one of the songs on their original demo tape, the one that got them signed to Innervision Records.
Later on, when Wham! were blowing up, Michael decided that he wanted to be a soul singer. There had already been plenty of R&B in Wham!’s sound, but Michael wanted to make smooth, heartfelt soul records on his own. He also wanted to keep Wham! going. The idea was that he’d make pop with Wham! and soul on his own. “Careless Whisper” was going to be the branching-off point, the introduction of what George Michael could do on his own.
Michael went to Alabama to record “Careless Whisper” at Muscle Shoals Sound Studio, a place where tons of classic soul records had been made in the ’60s and ’70s. Michael also enlisted a hall-of-fame producer: Jerry Wexler, the legend who had invented the term “rhythm and blues” and helped establish the Atlantic Records sound. (Wexler had only ever produced one #1 single: “Respect,” from future George Michael duet partner Aretha Franklin, which had topped the Hot 100 18 years before “Careless Whisper.”) With Jerry Wexler, Michael recorded a rich, buttery old-school version of “Careless Whisper.” But Michael didn’t like the way that version turned out. The Wexler version came out later, as a B-side.
Michael ended up producing “Careless Whisper” himself in London. He worked on the song for ages, never able to get it quite right. None of the session saxophonists could play the “Careless Whisper” riff exactly the way Michael envisioned it. He went through 11 different sax players before Steve Gregory, a session guy who’d previously played on the Rolling Stones’ chart-topper “Honky Tonk Women,” came in to try it. Gregory played the riff over a slowed-down version of the track, and then the engineer sped it back up. That turned out to be exactly the version of the riff that Michael wanted to capture, and that’s the one that came out.
All of those decisions worked out. Maybe Gregory’s version of the “Careless Whisper” riff was only microscopically different from all the previous ones, but there’s a primal power to that cheesed-out sax line, one that practically screams of smooth ’80s excess. In the annals of molten sax riffs on smoothed-out pop songs, “Careless Whisper” belongs right up there with Gerry Rafferty’s 1978 #2 hit “Baker Street.” (“Baker Street” is a 9.) That Steve Gregory saxophone sounds like soap-opera sex scenes and hair-weave commercials and overhead speakers and waterbed outlets. It sounds like the ultimate in chintzy luxury.
George Michael was right to ditch the Jerry Wexler take on the song. His own version is sleeker and more minimal, and it finds some uncanny sort of groove. The “Careless Whisper” arrangement is pretty simple — a slow-strut bassline, a few soft synth tones, some quasi-Spanish guitar flutters, that big sax riff. But the whole thing hits a pocket. Michael clearly does his best to capture the sound of American quiet-storm soul, but his own stripped-back production has some of the spacious whump of UK synthpop. Every element of the track has room to breathe.
Michael sings it beautifully, too. As an R&B singer, he’s direct and unshowy. Where way too many other white soul singers attempt growl-scream testifying, Michael eases his way into the song, letting the melody do most of the work for him. Even when he hits his big notes, Michael stays soft and intimate. That means those big notes — “To-night the music seeeeeems so loud” — carry a certain wounded vulnerability. As the song builds, Michael ramps up the drama, but he never loses that central fragility.
Lyrically, “Careless Whisper” is a pretty silly song. (Michael himself came to think very little of the track.) Michael’s narrator has cheated on a partner. He’s dancing with that partner, but guilt still tears him up inside, and he knows he won’t be able to keep the charade up for long. That’s a basic pop-song scenario, and Michael’s words are a little clumsy. The phrase “guilty feet have got no rhythm” looks at least a little bit ridiculous on paper. But Michael sells it. He sounds like he’s mourning something that hasn’t quite ended yet. “I feel so unsure,” he sings, and he sounds like he means it.
For the music video, Michael worked again with “Wake Me Up Before You Go-Go” director Duncan Gibbins, who would later make the sci-fi movie Eve Of Destruction. Gibbins and Michael shot the clip in Miami, and future Baywatch star Lisa Stahl played the cheated-on girlfriend. Apparently, they had to re-shoot a ton of it. Michael didn’t like the way his hair looked, so he flew back to London to get his hair re-done. But the clip works as effective kitsch, with those helicopter shots of the sailboat and Michael’s purple-lit Venetian-blind silhouette when he’s making out with the other girl. His hair looks spectacular.
Shortly after “Careless Whisper” hit #1 in the US, Wham! pulled off a magnificent publicity stunt, becoming the first Western pop group ever to tour the People’s Republic Of China. The footage of Michael singing “Careless Whisper” in China is truly fascinating. The people of China loved that shit.
But people everywhere loved “Careless Whisper.” It was true global smash, hitting #1 in Australia and Italy and South Africa and Poland and a half-dozen other countries. Notably, the song also did well enough on Black American radio that it reached #8 on the R&B charts. A couple of months after that China trip, George Michael sang “Careless Whisper” with Smokey Robinson, the American R&B singer who might’ve been his biggest influence, on the Motown Salutes The Apollo TV special. To his great credit, George Michael did not get blown offstage, and he did not lose this crowd.
Wham! will appear in this column again. So will George Michael.
BONUS BEATS: Here’s AZ, Nas, and Nature rapping over producer Dr. Dre’s “Careless Whisper” sample on AZ’s 2004 track “Time”:
(AZ’s highest-charting single is the 1995 Miss Jones collab “Sugar Hill,” which peaked at #25. Nas’ highest-charting single is 2003’s “I Can,” which peaked at #12. Nature, as far as I can tell, has never made the Hot 100. Dr. Dre will eventually appear in this column.)
BONUS BONUS BEATS: Here’s the South African quasi-grunge band Seether’s growly 2007 cover of “Careless Whisper”:
(Seether’s version of “Careless Whisper” peaked at #66. Seether’s highest-charting single is the 2004 Amy Lee collab “Broken,” which peaked at #20.)
BONUS BONUS BONUS BEATS: Here’s Ryan Reynolds mentioning “Careless Whisper” in the 2016 movie Deadpool:
And here’s end of the movie, where that bit pays off and “Careless Whisper” plays:
BONUS BONUS BONUS BONUS BEATS: Here’s El DeBarge and Kamasi Washington saluting George Michael after his death by covering “Careless Whisper” at the 2017 BET Awards:
(As a solo artist, El DeBarge’s highest-charting single is 1986’s “Who’s Johnny,” which peaked at #3. It’s an 8. As a member of DeBarge, his highest-charting single is 1985’s “Rhythm Of The Night,” which also peaked at #3. That one is a 9. El DeBarge was absolutely killing it on the soundtracks of ’80s movies that I watched over and over as a kid.)
BONUS BONUS BONUS BONUS BONUS BEATS: While scoring the 2019 TV series Watchmen, Trent Reznor and Atticus Ross covered “Careless Whisper” with Pomplamoose singer Nataly Dawn. Here’s their version of it:
(As the leader of Nine Inch Nails, Trent Reznor’s highest-charting single is 1999’s “The Day The World Went Away,” which peaked at #17. As Nine Inch Nails members, both Reznor and Ross will both appear, in sampled form, in this column.)
THE NUMBER TWOS: Billy Ocean’s slick, joyous quasi-rock stomper “Loverboy” peaked at #2 behind “Careless Whisper.” (It’s an 8.)