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The first time I ever heard Steely Dan’s music wasn’t on a Steely Dan recording. It was the mid-1990s, and I was in my early teens, listening to a cassette of De La Soul’s 3 Feet High and Rising (1989), a hip-hop album that blew my young mind. I wanted to hear one track in particular, a love song called “Eye Know,” over and over again: It was so effervescent, so totally joyful. A few years later, I learned that “Eye Know” was constructed around a sample of “Peg,” the fourth track of Steely Dan’s 1977 album, Aja. Meanwhile, another Aja sample was making the rounds in hip-hop: The opening track, “Black Cow,” was the bedrock for Lord Tariq and Peter Gunz’s 1997 rap-radio blockbuster, “Deja Vu (Uptown Baby).”

Music obsessive that I was, this confounded me. Steely Dan—the musical handle of the songwriting pair Walter Becker and Donald Fagen—was considered toxically uncool. Steely Dan was also in the midst of a decades-long hiatus from releasing new studio albums, after putting out seven from 1972 to 1980. I knew the band’s 1974 hit, “Rikki Don’t Lose That Number,” a steady presence on classic-rock radio, but I had trouble wrapping my head and ears around it. The guy singing in a plaintive, nasal voice seemed pretty sure that Rikki was, in fact, going to lose that number; every time he sang “And you could have a change of hea-a-art,” a gnarled run of notes followed that sounded oddly aggressive. I recognized the bass piano line from Horace Silver’s bossa-jazz chestnut “Song for My Father,” because I’d played it in my own jazz-piano lessons. But what was it doing in a pop song? “Rikki” ’s strange combination of jazz, rock, and R&B, alchemized into a near-frictionless sonic slickness, seemed antithetical to the grunge-era ethos of anti-establishment, heart-on-your-sleeve authenticity.

In hindsight, Steely Dan’s Zelig-like presence in sample-based hip-hop looks like a harbinger of the band’s current renaissance: A duo that was one of the most polarizing acts in rock even at its peak, in the 1970s, has lately acquired an army of new fans, many of them remarkably young. Listeners born well after the group made its best-known work are especially ardent, as social-media accounts with names like “Good Steely Dan Takes” and “People Dancing to Steely Dan” (both of which have tens of thousands of followers) attest. Steely Dan memes steadily proliferate on Twitter and Instagram and among the massively popular r/SteelyDan Reddit community. In 2019, the music publication Pitchfork—which had reviewed the band’s 2000 comeback album, Two Against Nature, with cooler-than-thou contempt and given it a score of 1.6 out of 10—published retrospective reviews of five of the band’s most esteemed studio albums; all of them were rated 8.3 or higher.

The pop-culture critic Alex Pappademas (who wrote one of those Pitchfork reviews) dives into this “Danaissance” in Quantum Criminals: Ramblers, Wild Gamblers, and Other Sole Survivors From the Songs of Steely Dan, a collection of illustrated essays dreamed up in collaboration with the artist Joan LeMay. The book doesn’t aspire to be a history of the band’s vicissitudes or a conventional march through its discography. Instead, Pappademas offers a lively series of ruminations about individual songs, loosely pegged to the characters who populate those songs and who are rendered in playfully detailed and colorful portraits by LeMay. The result is both a celebration and an artifact of the current Steely Dan moment.

Pappademas tries out several theories to explain the Danaissance’s timing. The most compelling of them is the idea that their songs, full of gallows humor and wry disillusionment, resonate with a generation raised on crashing economies and a climate crisis. “Donald and Walter’s songs of monied decadence, druggy disconnection, slow-motion apocalypse, and self-destructive escapism seemed satirically extreme way back when; now they seem prophetic,” he writes. “We are all Steely Dan characters now.”

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The truth is, Steely Dan’s trajectory has never been readily explicable. The band’s success defied rock-and-roll logic at every turn, starting with the fact that it wasn’t really a band. Steely Dan was the invention of two young men who had met at Bard College in the late 1960s and were obsessed with Bob Dylan and Charlie Parker in equal measure. Shortly after leaving Bard, Fagen and Becker moved to Los Angeles to become in-house songwriters for ABC/Dunhill Records. When their compositions proved too offbeat for other ABC artists to perform, the pair began to record the work themselves, with Fagen on keyboards and vocals, Becker on bass, and a roster of top-flight rock players rounding out the proceedings. ABC released Steely Dan’s first album, Can’t Buy a Thrill, in 1972. It sold 500,000 copies within weeks and spun off two hit singles, “Do It Again” and “Reelin’ in the Years.”

If Can’t Buy a Thrill had been the only album Steely Dan ever made, we would remember the band very differently. Fagen doesn’t even sing lead on three of the album’s tracks, and by Steely Dan’s later standards, the music is almost shaggy, full of jangling guitars and earworm radio-pop flourishes. It’s steeped in folk rock, Beatles-esque chord changes, and ’60s-vintage soul grooves. No other Steely Dan album feels quite so eager to be liked.

When Fagen and Becker followed up a year later with Countdown to Ecstasy, their true sound took shape. Their second album is full of dazzling rhythms, sophisticated harmonic structures, lyrics that are spiky and evocative and seethe with mordant disaffection. “Will you still have a song to sing when the razor boy comes and takes your fancy things away?” Fagen croons on “Razor Boy,” so mellifluously that you can easily miss that he’s singing about death.

After Countdown, nearly every aspect of Fagen and Becker’s project felt like a deliberate flouting of rock conventions. No sooner had 1974’s Pretzel Logic, propelled by the popularity of “Rikki Don’t Lose That Number,” become their biggest-selling album yet than Fagen and Becker decided to stop touring and reimagine Steely Dan as a purely studio-based entity. The duo proceeded to host a churn of crack session musicians, summoned to perform—at near-impossible levels of exactitude—compositions that grew ever more ambitious and technically demanding. Working with the producer Gary Katz and the engineer Roger Nichols, Fagen and Becker were in pursuit of perfect tones, perfect textures, perfect sounds. Steely Dan released two more studio albums—Katy Lied (1975) and The Royal Scam (1976)—before Aja in 1977, and Gaucho three years later. And then Steely Dan didn’t make another studio album for 20 years.

Like jazz greats of earlier generations, Fagen and Becker composed music full of dense harmonic structures and intricate arrangements. They openly worshipped at the feet of those masters: The only cover they ever recorded was a reverently faithful rendition of Duke Ellington’s 1926 classic “East St. Louis Toodle-oo,” which appeared on Pretzel Logic. (In case anyone missed it, the song was also included on Steely Dan’s 1978 Greatest Hits album.)

[From the May 1975 issue: Ellington in private]

They wrote surreal, scabrously witty songs about washed-up hipsters and failed threesomes, the incongruity of their buffed-to-a-shine sound adding to the humor. Their lyrics name-dropped a wide range of figures, among them the avant-garde mezzo-soprano Cathy Berberian; the Queen of Soul, Aretha Franklin; and Napoleon. They also wrote about unforgettably strange fictional figures who went by names like “Felonious,” “Kid Charlemagne,” and “Deacon Blues.” In sharp and funny chapters, Pappademas riffs on this cast of characters in ways that capture the band’s cultural context and musical debts. The inspiration for “Kid Charlemagne,” for example, is the hippie “Acid King” Augustus Owsley Stanley III—the principal LSD chemist for the Merry Pranksters and the Grateful Dead (as well as the Dead’s longtime soundman)—whose decline the song recounts. “Alone without a community of revolutionaries around him,” Pappademas writes, “he’s now just another criminal on the run.”

Steely Dan’s music posed a question: Was it possible to be an ironist and a perfectionist simultaneously? Was taking rock and roll this seriously a high-concept joke, or the only way to unlock the music’s full creative potential? Or had Steely Dan somehow come up with a blend of both, a virtuosic balancing act of scathing satire and fervent earnestness? At one point, Pappademas describes Fagen and Becker as “cynical about their own cynicism,” a phrase that hints at the fierce idealism that runs beneath the surface of even their iciest music.

Steely Dan’s Walter Becker (second from left) and Donald Fagen (far right) in 1973; others, from left to right: Jim Hodder, Denny Dias, and Jeff “Skunk” Baxter. (Michael Ochs Archives / Getty)

Such contradictions made Steely Dan an anomalous presence in the landscape of 1970s rock. The band-that-wasn’t-really-a-band was devoid of the phallic swagger of, say, Led Zeppelin or Aerosmith. While Bruce Springsteen was redefining heroic authenticity and gracing the covers of national magazines, Fagen and Becker retreated behind their retinue of characters. Steely Dan’s ever-changing lineups deprived the band’s public of the personality-driven soap operas that fans thrilled to in groups such as the Rolling Stones and Fleetwood Mac. The pair’s refusal to tour stood out as arena rock became a massive business; Fagen and Becker never even appeared on one of their studio-album covers. At a time when rock stardom was synonymous with being cool, the two of them seemed uninterested in being rock stars and completely indifferent to being cool.

Aja’s success was unusual, even for this unusual band. Released just weeks after Elvis Presley died and in the middle of the year that punk broke, the album became the biggest commercial hit of Steely Dan’s career, peaking at No. 3 on the Billboard album chart. Fans debate whether it’s the best Steely Dan album, but it’s certainly the quintessential Steely Dan album. An extraordinary fusion of styles filtered through the duo’s explosively ambitious songcraft and sonic architecture, Aja features more than 30 credited musicians, a who’s who of the world’s top jazz, rock, and R&B session players.

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An old joke about Steely Dan’s reliance on studio musicians has it that Fagen and Becker were writing music so difficult that they couldn’t even play it themselves. This isn’t true: Both were terrific instrumentalists and can be heard all over Aja. Still, the deployment of so many hired guns was one of the most controversial and misunderstood aspects of their endeavor; detractors, viewing it as proof of prefab inauthenticity, disparaged Steely Dan as essentially a factory dedicated to turning out the world’s most finely tuned musical product.

But enlisting studio players, far from an abdication of artistic vision, was a fanatical assertion of Fagen and Becker’s vision. The fantasy that rock-and-roll bands are democracies—melting pots of individual contributions and sensibilities, wholes greater than the sum of their parts—is deep-seated and attractive. By Aja, Steely Dan had dispensed with such notions (if its founders had ever embraced them): Fagen and Becker were the bosses, and everyone else was an employee. To use a famous example, the pair reportedly brought in as many as eight different guitarists to try playing the roughly 25-second guitar solo on “Peg.” (Jay Graydon finally got it, after what he later recalled as “four, five hours” of takes.)

From one angle, this looks like tyrannical micromanagement; from another, it looks like the sort of uncompromising rigor and sacrifice—of time, money, and other people’s individual talent—in the service of a relentless aspiration that certain great art requires. In the case of Steely Dan, listeners can find themselves under unforgiving pressure too: Insistent about making music entirely on their terms, Fagen and Becker deliver a sound defined by calculating precision, one that offers little of the visceral thrill of impulsivity that many fans expect from rock music. It’s a listening experience that some will find deeply alienating, others endlessly alluring.

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“There are artists who don’t work this way,” Pappademas writes, “but none of them have made ‘Peg,’ ” a song that he extols in terms that distill the Steely Dan aesthetic: It’s “a hundred layers carefully positioned to create the illusion of casual cohesion, a whole ecosystem arrayed in a shape as sleek as a surfboard.” As detail-oriented as his muses, Pappademas dedicates an entire paragraph in an essay about “Show Biz Kids”—a song he identifies as the very first rock song “about being afraid of people younger and cooler than you”—to a four-bar phrase that occurs three minutes and 49 seconds in and lasts about seven seconds itself. The fleeting moment might seem tossed-off: The guitar drops out and we’re left with a roiling marimba and Fagen intoning a profane line about Hollywood scions (“They don’t give a fuck about anybody else”). But Pappademas, fastening on that small but crucial arrangement choice, pronounces it “the coolest and therefore most important part of the song.” “Yes!” I exclaimed, instantly appreciating his insight.

Fully accounting for the collective “Yes!” that is now greeting Steely Dan may be hopeless, but the lineage of that yes is rich and suggestive. Decades ago, young hip-hop artists stumbled upon Steely Dan because of the band’s popularity among a slightly older generation of Black listeners—De La Soul’s Kelvin Mercer (also known as Posdnuos) has recalled first listening to “Peg” as a child with his father, years before the sample found its way onto 3 Feet High and Rising. Now, as a new generation of listeners discovers the band, the sonic and stylistic polish of Steely Dan that seemed so divisive in the ’70s—and in the ’90s—is evidently no longer such a deterrent. Slick doesn’t carry the sting that it used to.

For those weary of the “rockism”-versus-“poptimism” debates of the past couple of decades—and who isn’t?—Steely Dan offers a welcome escape from the reductive opposition between rock as Promethean self-expression and pop as a big-tent pleasure center. The band didn’t mind being dismissed by the most doctrinaire rock partisans: “soulless, and by its calculated nature antithetical to what rock should be,” as a Rolling Stone review of Aja summed up the brief against them. At the same time, Steely Dan’s music is unapologetically snobbish, flouting the “everything is great” ethos of extreme poptimism.

A band that charts an idiosyncratic path ends up acquiring an eclectic audience, this one united by a tenacious devotion to the work of a pair of artists who were themselves nothing if not devoted. When I became a full-fledged Steely Dan fan in my 20s, I found the depth of care and attention in Fagen and Becker’s music deeply moving, even romantic. If the lyrics were often cynical, everything else felt like the opposite, and the tensions held in Steely Dan’s sound spoke to, well, my soul. I’m glad to know I have new company.

This article appears in the June 2023 print edition with the headline “Surrender to Steely Dan.”