Here Are My Picks for the Top 5 Singles from 1977-1999 for #UncoolTwo50

Photo taken by the author of The Flaming Lips' Wayne Coyne in a bubble, rolling over the crowd at Lollapalooza 2006, moments before the band broke into "Race for the Prize."

For the last 45 days, I’ve been participating in another Blue Sky music challenge: #UncoolTwo50.  Organized by the account @uncooltwo50.bsky.social, the idea is to is the share your picks for the 50 best songs released as singles between 1977 and 1999. It’s all part of a multi-year project to crowdsource one giant list covering the history of recorded music.

The hashtag has baffled the recent influx of Blue Sky users—including Flavor Flav himself!—and understandably so. The name is inspired by the book “This is Uncool: The 500 Greatest Singles Since Punk and Disco” by music journalist Garry Mulholland. It does not mean that wide swaths of the pop cannon are now “uncool,” so you can all just relax.

One of the things that more committed participants in the broader Ultimate Pop 1000 project apparently like to do is to “blurb” their selections, i.e. writing some extra blah blah about the song and its significance. I couldn’t quite commit to blurbing all 50 of my songs, but I’m going to try to do it for the Top 5, starting now with …

5. “I Can’t Go for That (No Can Do),” Hall & Oates (1981)

This is, incredibly, my highest-ranked song that no other #UncoolTwo50 participant has selected. There’s still four days left, but shit man. Y’all were gushing about the bassline to “Billie Jean,” but not the song that Michael Jackson himself said he lifted it from (according to 100% objective posthumous accounts from Daryl Hall and John Oates, at any rate)?

I’m just kidding. Kind of.

My appreciation for this tune, as is the case with many in my Top 50, started semi-ironically. If there’s something on my list that falls more on the side of “cheesy dance pop” than “self-important alt-rock,” chances are it was on a playlist I threw together in my 20s when I lived in a party house in a smallish blue-collar Michigan town, and my housemates and I would invite the entire dive bar to come on over after closing time. After a couple 3 a.m. dance parties, the songs I’d thrown on as tongue-in-cheek larks started to seem more inspired. After a few more, they reveled themselves as the work of pop-savant geniuses.

No song benefitted more from these beer- and groove-fueled revelations than “I Can’t Go For That Parenthesis No Can Do Close Parenthesis.” Twenty-five years after it entered the pop charts, the blue-eyed soul and twinkling synths of Hall & Oates, without fail, transformed these after-hours gatherings into a sexy, silly communion of mostly white boys united in the escapism and euphoria of dance. They are some of my fondest memories of that era of my life. Plus it has a saxophone solo.

4. “Under Pressure,” Queen & David Bowie (1981)

It’s partially the pairing of Bowie with another superstar rock icon—but not just that, because otherwise we’d be seeing just as many points going to “Dancing in the Street,” right? It’s partially that bass riff—but the existence of “Ice Ice Baby” proves it’s not that alone. And sure, there are the humane lyrics about supporting each other a cruel and uncertain world, but there’s also an awful lot of mmm ba dee ba doo bahs. I submit to you that the structure of “Under Pressure” is what elevates it to masterpiece. It is epic in scope, and it unfolds in dramatic and unexpected ways.

Let’s return to “Ice Ice Baby” for a moment. I was in sixth grade when that abomination came out. I’m proud to say I hated it immediately. Its only redeeming quality, as far as I was concerned, was that undeniable bassline combined with those beguiling open fifths on the piano. That was intriguing.

As the ’90s continued, and alt-rock radio started to rediscover both Bowie and Queen, I remember riding in the car with my mom one day when “Under Pressure” came on. My immediate impulse was to change the station, quick before “Stop! Collaborate and listen!” But then the electric guitar came in, and my mother—a music major who knew her theory—remarked at how she’d gotten so used to hearing that bass riff in a minor mode. I didn’t know what was going on. I don’t think I’d realized “Ice Ice Baby” was built on a famous sample until that moment. (Keep in mind that my pop culture awareness blossomed in that weird period between Live Aid and “Wayne’s World,” when Queen was a foundering nonentity.) Then the song kept going and going, building to its dramatic climax, with Bowie and Mercury singing in unison before everything boils back down to that simple two-note bass figure. Oh, and in that moment I realized just how much I hated “Ice Ice Baby.” Vanilla Ice and his co-conspirators had not merely grifted their way onto the charts with the the stolen valor of a memorable riff, they had robbed it of all its gradually revealed harmonic complexity.

Sorry, I didn’t mean to spend 80% of this blurb talking about “Ice Ice Baby.” “Under Pressure” obviously stands on its own. But a diamond shines even brighter when placed next to a diamond-shaped turd.

3. “6 Underground,” Sneaker Pimps (1996)

Music journalist Simon Price famously called Sneaker Pimps “the Stone Temple Pilots of the Bristol Sound,” and surely he meant it as (derogatory), but if you’ve been following my #UncoolTwo50 countdown from the beginning, you know that reads to me as (complimentary). Like STP, Sneaker Pimps weren’t breaking any new ground within their respective genre. “6 Underground” has all the trip-hop trappings: sultry female vocals; downtempo, melancholy beats; even a ’60s film-music sample (in this case, the horns and harp are from the Goldfinger soundtrack). But it’s perfectly executed to take those elements to their most accessible, transcendent, promised pop destination.

I get the impression that by the time “6 Underground” came along, trip hop was already past its peak in Europe, but the genre never achieved enough popularity here in the U.S. to have a backlash. And “6 Underground” is the song that had the closest thing to a mainstream breakthrough. The only other candidate is “Sour Times,” and that pretty much stayed relegated to alternative rock radio. With this song, Sneaker Pimps reached No. 31 on the U.S. Adult Pop Airplay chart No. 45 on the Billboard Hot 100. As such, for us Americans, it is probably the ultimate tip hop track.

2. “The Boy in the Bubble,” Paul Simon (1986)

Most of us know, of course, the broad strokes of the story of Graceland. That Paul Simon found himself in a bit of a spiritual wilderness after the commercial failure of Hearts and Bones and the near-immediate collapse of his marriage to Carrie Fisher. That he got a little obsessed with a bootleg cassette tape of South African street music. That he traveled to Johannesburg in the midst of Apartheid and spent weeks recording with a roster of talented black musicians. That the resulting album combined some of the strongest pop-folk songwriting of Simon’s post-Garfunkle career with sounds, rhythms, and styles unknown to Western audiences. That it threw Simon up the pop charts and won all the awards in spite of swirling controversies over appropriation and Simon’s violation of the ongoing cultural boycott of South Africa.

“The Boy in the Bubble” was one of the first songs completed. Simon says it was always intended to be the album’s opening track, and that the drums hits in the intro were meant to sound “African” and to serve as a proclamation: “You haven’t heard this before.” The song’s creation was emblematic of the process Simon and recording engineer Roy Halee employed. Simon tracked down the musicians who played on one of the songs he’d discovered, “Ha Peete” by the Lesotho band Tau Ea Matsekha. In that song, you can hear the bones of “The Boy in the Bubble,” particular in the way Forere Motloheloa’s accordion provides the rhythnic foundation while South African session musician Bakithi Kumalo’s fretless bass acts almost as a lead instrument. At Ovation Studios in Johannesburg, Halee recorded an extended jam of Simon playing with the group. Then they took that recording back to New York, snipped it, edited it, muted some elements, and added synth and drum samples to give it more heft.

Motloheloa’s accordion riff was such an important contribution that he got a songwriting credit out of it, while Kumalo’s fretless bass became a central element to the overall sound of Graceland. Simon brought him to New York to record additional parts and he basically never left.

“The way the camera follows us in slo-mo, the way we look to us all,” were reportedly the only lyrics on all of Graceland that Simon came up with while in Africa. Everything else was written afterward to fit the groove of the recorded jams. For “The Boy in the Bubble,” Simon said the he wanted to evoke both hope and dread, and it treads that line so well that people walk away from the song with completely different emotional reactions. For me, the promise of “these are the days of miracle and wonder” rings hollow, coming immediately after a description of a terrorist bombing. The wonders of new technology seem ill prepared to deal with a society coming apart, environmental collapse, conspiracy theories, and the consolidation of power under a loose affiliation of millionaires and billionaires. I wish I could say that interpretation has become a dated concern in the ensuing 38 years, but I’m afraid this song only sounds more and more relevant to my ears.

1. “Race for the Prize,” The Flaming Lips (1999)

Pop-culture critic Kyle Anderson has a short write-up he did eight years ago about his personal connections to this song, including the time he saw it performed at Lollapalooza 2006. He was covering the festival for Spin and ended up on stage in a Santa Claus costume (it’s a Flaming Lips thing), miserable and sweltering in the summer Chicago heat. “But as soon as I got a look at the rapturous crowd,” he wrote, “and the Lips laced into ‘Race for the Prize,’ I lost my damn mind. The opening drum slaps of that song still send me to that place.” Well, I was one of the folks in that rapturous crowd at that very show, looking up at the dancers on stage in Santa Claus costumes. And like Anderson, I lost my damn mind that day. I cannot hear the song without being transported back to that euphoric performance and the overwhelming sensory experience of being hit by a wall of woozy synths and streamers mere moments after nearly touching Wayne Coyne’s hamster ball as he rolled by (see photo at top).

The mythos goes like this: “Race for the Prize” heralded the third incarnation of The Flaming Lips. They’d started as noise-rock hooligans in the ’80s who barely knew how to play their instruments, then joined the ranks grunge one-hit-wonders in the ’90s. Where could they possibly go from there? After guitarist Ronald Jones left the band following the commercial failure of 1996’s (artistically excellent) Clouds Taste Metallic, Coyne started pushing DIY artistic boundaries. First there were the “Parking Lot Experiments,” which involved volunteers in 40 cars pushing 40 different cassettes into their respective tape decks on command. The band somehow talked Warner Bros. into giving fans a chance to approximate that experience in their homes with Zaireeka, an album that came on four discs designed to be played simultaneously on four different sound systems. As someone who has hosted a “Zaireeka party,” the effect of listening to the album in its intended format is disorienting. No matter how you try, the discs are never 100% in sync, which transports you to an uncanny valley that almost sounds like alt-rock, but something is off.

For their next album, The Flaming Lips wanted to retain a bit of that sensation in a format that required just a single CD player, while also steadfastly refusing to replace Jones. The result was The Soft Bulletin, an album that eschews electric guitars and has been likened to a post-modern Pet Sounds meets demented Disney soundtrack meets generational therapy session. And it all kicks off with “Race for the Prize.”

In Pitchfork’s highly recommended oral history of The Soft Bulletin, “Race for the Prize” is introduced accompanied by intercut visuals of Leonard Bernstein conducting atomic bomb blasts, which seems about right. Bassist Michael Ivins says that when they first previewed the song for people, their reaction was, “My stereo sounds like it’s broken.”

Between this and “Under Pressure” and “The Boy in the Bubble,” my Top 5 seems to have a through-line of songs exploring … well, “the terror of knowing what this world is about.” Human achievement reaches new heights but is unable to meet the moment and leaves misery and loss and ennui in its wake. The scientists in “The Race for the Prize” are prepared to sacrifice all to save the human race from some unspoken pathological horror, but they can only do so through the lens of competition and posthumous glory. The idea that they could work together and pool their knowledge is never given a moment’s consideration. All the while, the desperate banging of the drums and the vertigo of detuned keyboards make it sound like the whole contraption might fly apart at any minute.

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