This is the 53rd post in a weekly series. Read about it here and see the list of previous songs here. A new post about a different song is posted each Monday. You can listen to the songs in a Spotify playlist.

George Michael and Andrew Ridgeley met when they sat next to each other in school. They formed a ska group called The Executive, but that quickly broke up, and they then formed a pop duo they called Wham! The two recorded a demo, which included snippets of songs called “Wham Rap!” and “Careless Whisper.” Ridgeley shared the demo in early 1982 with his friend Mark Dean, who ran a label called Innervision. Wham! was signed within a month.

Wham! released its debut album, “Fantastic,” through Innervision in 1983. The album produced four singles, all of which charted: “Wham Rap! (Enjoy what You Do)”, “Young Guns (Go For It)”, “Bad Boys” and “Club Tropicana.” But despite those successes, Michael and Ridgeley found themselves broke.

Jazz Summers, a manager, and his business partner Simon Napier-Bell approached Michael and Ridgeley to persuade them that Summers and and Napier-Bell should become Wham!’s new managers. Michael and Ridgeley agreed, and Summers sued for Wham! to be independent from Innervision.

In 1984, Wham! released its second album, the critically and commercially successful “Make It Big.” Two singles — “Wake Me Up Before You Go-Go” and “Freedom” — reached Number 1 in the UK. Additionally, “Careless Whisper” was finally released. But it was released as a George Michael solo song, rather than a Wham! song. The irony was that “Careless Whisper” was co-written by Ridgeley, whereas most of the tracks released by Wham! were written by Michael.

Michael had originally recorded the song at Muscle Shoals Sound Studios at the urging of Atlantic Records producer Jerry Wexler, but Michael was unhappy with that version because he thought the saxophone riff wasn’t quite right. He returned to London to re-record the version that was ultimately released, but the Muscle Shoals version appeared as a B-side in Japan and the UK.

“Careless Whisper” became a huge hit, eventually peaking at Number 1 in the UK, the US, Canada, Australia, The Netherlands, Ireland, Italy, Japan, South Africa, and Switzerland. By the end of 1984, Michael had reached Number 1 on the UK charts as part of three different entities: as a member of Wham!; as part of Bob Geldof’s Band Aid, for “Do They Know It’s Christmas?”; and as a solo artist, for “Careless Whisper.”

Michael and Ridgeley had written the song when they were just 17, taking inspiration from some of Michael’s romantic drama when he was a teenager. Michael explained in his book “Bare”:

I used to have to chaperone my sister, who was two years older, to an ice rink at Queensway in London.“There was a girl there with long blonde hair whose name was Jane.“I was a fat boy in glasses and I had a crush on her — though I didn’t stand a chance. My sister used to go and do what she wanted when we got to the rink and I would spend the afternoon swooning over this girl Jane.

A few years later, when I was 16, I had my first longish relationship with a girl called Helen. It had just started to cool off a bit when I learned that the blonde girl from Queensway had moved in just round the corner from my school. One day I saw her walk down the path next to me and I thought, Where did she come from?’

We played a school disco with The Executive and she saw me singing and decided she fancied me. By this time she was that much older and a big buxom thing, and eventually I started seeing her. She invited me in one day and I was in heaven. I couldn’t believe that all my dreams were coming true. I didn’t wear glasses any more. I got invited to parties. And the girl who didn’t even see me when I was 12 invited me in.

We went out for a couple of months but I didn’t stop seeing Helen. I thought I was being smart. I had gone from a total loser to being a two-timer. The whole idea of Careless Whisper was the first girl finding out about the second, which she never did.

But he ended up two-timing Jane, and she did find out.

Not only did “Careless Whisper” become one of Michael’s signature songs, it has become one of his most covered.

In 1985, Michael performed the song with Smokey Robinson at The Apollo Theater in Harlem for a 50th anniversary show. It was a fantastic duet that brought together a Motown legend with a Motown fan, but it’s hard to watch the performance now without fixating on Michael’s almost-a-mullet or Robinson’s creepy mustache.

Gloria Gaynor’s 1986 album, “The Power,” featured mostly covers of contemporary songs. Though not on the original album, a cover of “Careless Whisper” appeared on reissues. Gaynor’s take on the song sounded too subdued given that her default style is disco. Her voice sounds best when she’s evoking a the spirit of gospel over a bass line with a beat. Having her do a quiet ballad is like having Eddie Van Halen play an acoustic guitar: it’s possible, but a complete waste of their best assets.

Singer Mina, a prolific generator of Italian pop music in the ’60s and ’70s, included “Careless Whisper” on her 1987 album, “Rane Supreme.” Taking her time over six minutes, Mina proved that with her her soprano voice and three-octave range, she could make anything sound soulful and seductive.

Canadian singer Tamia’s 1998 self-titled debut studio album, which featured her hit “So Into You,” also included a cover of “Careless Whisper.” Michael had performed the song as a soulful ballad, and Tamia picked it up where he left off, adding R&B flourishes to make it more sultry. “So Into You” had displayed Tamia’s pop sensibilities, but this showed she could sing and could creatively approach a song we had already heard hundreds of times.

Bananarama’s 2001 album “Exotica” featured new songs and reinterpretations of past Bananarama hits. Additionally, the group — at that point a duo — recorded a comparatively dialed-back cover of “Careless Whisper.” I say “comparatively” because no Bananarama track can be truly “subdued,” but on this version, the iconic saxophone was ditched in favor of a strings-like keyboard track that sounded like it could have been used for a James Bond theme.

Saxophonist Kenny G.’s 2005 album, “At Last… The Duets Album,” paired him with several musicians from throughout the years, including Burt Bacharach, LeAnn Rimes, Chaka Khan, and Daryl Hall. His version of “Careless Whisper,” with Brian McKnight and Earl Klugh, made the original seem gritty in its aesthetic, and that’s saying something considering that Michael’s “Careless Whisper” was already a staple of easy listening stations. McKnight and Kenny G. saw Michael’s cheese and raised him a bulk pack of Velveeta. McKnight, ever an emotive singer, pushed it above elevator music level. That put it in early morning at an empty airport level, but still above elevator music.

Julio Iglesias’ 2006 album, “Romantic Classics,” included covers of songs from several eras, including “Always On My Mind.” The crooner’s version of “Careless Whisper” was so earnestly faithful to the original that it’s hard to believe it wasn’t a prank or a parody. The chorus of backup singers kicked in to sing “Tonight the music seems so loud,” giving the song its most natural-sounding moment.

For BBC Radio 1’s 40th anniversary, the station recorded 40 cover songs with 40 artists, with each song representing a different year. Gossip, a band able to make you rock out while dancing your ass off, recast “Careless Whisper” as a frenetic dance jam driven by guitars and drums, rather than the iconic sax. It worked, in part because Beth Ditto managed to keep all the same emotional nuance as Michael’s original.

Quebec band The Lost Fingers’ jazz- and swing-inspired style has made for fun reinterpretations of pop classics, and on the band’s 2008 album, “Lost in the 80s,” featured covers of some of the biggest hits of the decade. The Lost Fingers’ “Careless Whisper” was so bouncy that it was hard to imagine it being performed by band of swanky people in three-piece suits and fancy hats.

If the cover of “Careless Whisper” by Kenny G. and Brian McKnight was a “bulk pack of Velveeta,” then Barry Manilow’s version was a Velteeta distribution plant. The faithful cover appeared on Manilow’s 38th album, “The Greatest Songs of the Eighties,” which was the follow-up to his 2007 album, “The Greatest Songs of the Seventies.”

Metal band Seether covered “Careless Whisper” in 2009, trading all the nuance of Michael’s original to make an aggressively emo version. Michael had imbued his words with a sense of regret, anger, sadness, culpability, and acceptance, but none of that carried over to Seether’s cover. In Seether’s hands, “Careless Whisper” was a complaint from an oblivious narrator, unable to see he was responsible for his mess.

Brian McKnight released his own version of “Careless Whisper” on the appropriately titled 2011 album, “Just Me.” Without Kenny G., McKnight recast the ballad as a slower jazz song, with piano taking the part of the saxophone. By adding pauses and adjusting the phrasing, McKnight made the narrator seem angsty, frustrated, and unsettled. Which, as the lyrics would indicate, seems appropriate for the song.

Singer-cellist Erica Mulkey, who performs as Unwoman, has created a niche for herself recording dark cello covers. We previously reviewed her cover “Seven Nation Army” for her album “Lemniscate: Uncovered Volume 2.” But on her 2011 covers album, “Uncovered Volume 1,” she limited herself to songs written between 1980 and 1995, focusing on songs that were important to Mulkey during her childhood. Among those was a hauntingly layered “Careless Whisper.” As she does on so many of her tracks, Unwoman can convey a dark tone without being gloomy or cold. There was a Goth intimation to her rendition, to be sure, but she does so with a surprisingly inviting warmth.

Ben Folds included a live version of “Careless Whisper” on his 2011 compilation, “The Best Imitation of Myself: A Retrospective.” On the song, Folds traded off lines with Rufus Wainwright, and it’s easy to hear not only that they each love the song, but that these two are having fun playing off each other.

Brazilian band Kiara Rocks jettisoned the saxophone for crunchy guitars and pounding drums on its 2012 cover of “Careless Whisper” for the album, “Todos Os Meus Passos.” As was the case for Seether’s cover, Kiara Rocks’ “Careless Whisper” lacks the complexity of Michael’s delivery. Where he was able to convey several emotions, Kiara Rocks and Seether conveyed screaming. And whining.

Scott Bradlee’s Postmodern Jukebox, which has made a name for itself making stylized, old-timey versions of modern pop hits, remade “Careless Whisper” as a jazz song with peppy piano for the 2014 album, “Clubbin’ With Grandpa.” Postmodern Jukebox videos tend to include period-specific clothes, but even if you were only listening to this and not watching the video, it’s hard to not imagine this being performed in an old-timey jazz club.

After Michael’s death, the newspaper The Sun launched a campaign to re-release “Careless Whisper” to raise money for some of Michael’s favorite charities. Andrew Ridgeley pushed back, saying a song Michael wrote by himself as a solo artist should be re-released, rather than something from his Wham! days. To Ridgeley, Michael would have been more comfortable being remembered for his solo work.

Ridgeley’s probably right. For his part, Michael seemed shocked — maybe even dismayed — that “Careless Whisper” became such a huge hit. It seemed he would rather be remembered for other songs. In a 2009 interview with The Big Issue, he said:

I’m still a bit puzzled why it’s made such an impression on people… Is it because so many people have cheated on their partners? Is that why they connect with it? I have no idea, but it’s ironic that this song – which has come to define me in some way – should have been written right at the beginning of my career when I was still so young… I was only 17 and didn’t really know much about anything – and certainly nothing much about relationships.

But Michael’s naive perspective is probably what made the song resonate so well in the first place. It came from an earnest place that is hard to inhabit if you’re older and more experienced. Michael’s later songs had more edge and sophistication, but “Careless Whisper” captures something we all remember: the angst of being a teenager and the soap-level drama that came with dating. That’s part of its nostalgic appeal. (That, and Michael’s bodacious, feathered hair.)

Michael wouldn’t have written that song as an adult. He surely wouldn’t have included the line “guilty feet have got no rhythm.” Which would be a shame, because it’s one of the best lyrics in pop music history.

You can listen to these songs and previously discussed cover songs in a Spotify playlist.
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