To look at American society over the past decade—from its memes, to its cultural criticism, to even its electoral politics—one might surmise the nation is consumed by a bitter and Manichean generational struggle, where no quarter is given and none taken over the power baby boomers wield as they cling to institutional power.
Maybe so. But there are notable exceptions, and perhaps the most notable comes from the medium through which the boomers shaped America’s cultural identity for decades: classic rock. Steely Dan, the jazz-rock combo whose musical and lyrical checkpoints include those most boomer-ish of pursuits such as cool jazz, hot guitar licks, tiki drinks, and expensive cocaine, have become an object of millennial obsession, spawning viral tweets, mash-ups, and even a custom run of streetwear emblazoned with their album art. John Mulaney and Nick Kroll wrote a bit based on Steely Dan for their hit Broadway show Oh, Hello. David Crosby, a fellow Boomer icon who’s become a Twitter favorite in his own right, earned blog press with a new Dan-inspired (and cowritten) tune. The list goes on.
Even in their time, Steely Dan were one of rock’s most idiosyncratic outfits—they covered Duke Ellington, peppered their records with references to obscure spiritualist sci-fi authors, and foreswore the big-time arena rock touring circuit at their (and its) peak. Of all this, what about them led millennials to pluck the band from the genre’s back pages, placing them on the shelf of honor next to legacy acts like Fleetwood Mac or Bruce Springsteen who have renewed their cred in a similar fashion?
Attempting to explain why certain music goes in and out of vogue might be, to reference the quote apocryphally attributed to the comedian Martin Mull, like “dancing about architecture.” But in taking a stab at it, it’s only fair to offer the first opportunity to the architect of the music in question: Donald Fagen, Steely Dan’s lead vocalist, co-songwriter, and bandleader, whom I spoke with earlier this summer by phone.
“Developmental psychology might figure in,” Fagen wrote to me after our conversation. “Kids and teens resent the domination of the parents—they begin as hostages to their dad’s taste in music. Of course they hate it (though, in truth the stuff we wrote used tropes more common to the popular music of their grandpops). As they head into middle age, a lot of kids start to forgive their parents … so, as the prejudices of their youth crumble a bit, they’re free to be more objective about what they hear—or, they might even have a subliminal, sentimental attachment to sounds they heard in the womb, in the kitchen, in the back seat of their dad’s car—or something like that.”
Fagen’s insight is spot on, true to both his body of lyrical work and the sharp cultural criticism he’s written for outlets like Slate and Harper’s Bazaar. Millennials are, of course, growing into their own soft middle age, where one’s identity is less defined by the cultural postures of youth than the big choices one might have made (or not made) while striking them. Their taste, then, is freed up to roam toward what they might have once overlooked as outré.
In that light, it’s easier to see Steely Dan’s music as its savvier observers always have: not a smooth-jazz accoutrement to the spoils of boomer aristocracy, but an über-sardonic critique of it. And in addition to the generational shift, there’s an aesthetic one: Pop music, broadly defined, gains its cultural currency through an antagonistic relationship to the status quo. When it comes to the counterculture of the past few decades, Steely Dan’s music has been anything but part of that firmament.
“There’s a knee-jerk, reactive way that cultural fashion evolves in its time,” says Robert Christgau, the “dean of American rock critics” and an avowed fan of the Dan. “Punk—now that’s, like, so old hat. Your generation’s immediate elders are always putting it in your face. … And there’s also indie rock, not quite the same thing, which people are also now finding tedious.”
“There are cycles with things that are completely organic, that’s built into being alive,” he continues. “And so far as you’re using your brain, which as a critic, you really should be, music doesn’t suddenly disappear.”
The music of Steely Dan is now very much un-disappeared, with the help of the aforementioned litany of memes, the archival resource that is Spotify, and a now-immortal (and ubiquitous) clip from The Sopranos featuring James Gandolfini belting out one of their early hits. The band is no stranger to the whims of cultural fashion: rightly celebrated by the 1970s’ savviest critics for their acerbic lyrics, musical creativity, and impeccable songwriting chops, by 2001 their Grammy win for the (excellent) comeback album Two Against Nature was met in the wider culture with utter bewilderment. But their newfound (or rediscovered) popularity isn’t due just to their role in a game of 4-D generational chess or the ever-spinning wheel of pop modishness.
The spirit of Steely Dan’s music—wry and detached, but in the way only a true-blue bruised optimist can be—is one that’s uniquely suited to a certain kind of music listener and kindred spirit today. Its essence is present in nearly all of the discourse around the band, from the winking acknowledgement of encroaching middle age, to the sardonic cultural criticism that runs through their discography, to an awed, almost jealous appreciation of their peerless chops and the lavish perfectionism afforded by a bygone and less-stingy era of the music industry. And to understand how it’s endured for five decades now since their inception in 1971, you have to go back to those beginnings—when they, too, were on the outside, yearning for something more.
Before they were Steely Dan, Fagen and the band’s cofounder, Walter Becker, were jazz-loving misfit students at Bard College. As Fagen wrote after Becker’s death in 2017, the two “started writing nutty little tunes on an upright piano in a small sitting room” in the late 1960s, bonding over their shared love of “jazz (from the ’20s through the mid-’60s), W.C. Fields, the Marx Brothers, science fiction, Nabokov, Kurt Vonnegut, Thomas Berger, and Robert Altman films.”
Their hardcore eclecticism was matched with a penchant for black humor that led Jay and the Americans’ bandleader Jay Black to famously dub them the “Manson and Starkweather of rock ‘n’ roll” during the duo’s pre–Steely Dan stint as members of his touring band. That disposition made them somewhat ill-suited for their original career aspiration, Brill Building songwriters for artists like Barbra Streisand (for whom they did, improbably, land a 1971 album track). So they struck out to the West Coast to form the band’s earliest recording incarnation: one that could handle their complex, razorblade-in-a-candy-apple pop songs.
It’s a theme that would pop up time and time again through their career: the wheels spinning just a little too fast, the frame of reference just a little too off-kilter, the sheet music just a little too complex to be fully appreciated even at the height of their commercial success. There’s “Reelin’ in the Years,” a bitter kiss-off to youthful expediency mistook for a straightforwardly nostalgic anthem. Or the title track from Aja, which smuggles extended solos from jazz legends Wayne Shorter and Steve Gadd onto a silky-smooth, multiplatinum pop album. The band’s catalog invites so much graduate-level analysis that some obsessive fans insisted that their biggest chart hit, 1974’s “Rikki Don’t Lose That Number,” was a coded primer on how to send marijuana through the mail. (Becker later denied it, asserting the song is as simple of a romantic come-on as it sounds.)
“Something like ‘Bad Sneakers,’ you’re taking a very pop melody but finding these different chords that are modifications of quote-unquote ‘normal’ chords,” says Winston Cook-Wilson, frontman and songwriter for the Dan-influenced New York band Office Culture and host of the Late Era podcast. “They move to different keys, doing this really, really difficult stuff.”
As the ’70s wore on and they racked up the hits, Steely Dan evolved from the idiosyncratic hitmakers behind radio staples like “Do It Again” and the aforementioned “Reelin’ in the Years” to an increasingly studio-focused project, their songs becoming more and more complex. Eventually, like the Beatles and Brian Wilson before them, the group ditched touring altogether in favor of their quest for studio perfection. That resulted in the two records that now stand alone in their discography, metonymic for their singular combination of smoothness and acidity: 1977’s Aja and 1980’s Gaucho, the last they would record before a hiatus of more than a decade.
When Pitchfork turned its critical eye to the band’s discography for a “Steely Dan Day” in 2019, the critic Alex Pappademas described Gaucho as a “pathologically overdetermined … flawless-sounding” record “about breakups and estrangements and encroaching age and the corrosive effects of hard drugs on human fellowship,” “the most Steely Dan of the Steely Dan albums.” It’s the Steely Dan of Gaucho and its predecessor that’s lived in the cultural imagination for decades: first with audiences’ gross misperception of them as peddlers of inoffensive elevator music, and now as the shared fixation of a generation less obsessed with its predecessors’ frequently affected “authenticity” and narrow boundaries of taste.
“A cleaner, smoother aesthetic has seeped into a lot of elements of indie rock and pop; it’s more OK for things to be clean,” says Cook-Wilson. “And then there’s their history with rap, and Kanye sampling them, which preceded all of this—listening to Steely Dan in some sense aesthetically is like listening to DJ Quik [records] from 1997… people caught onto the contrast between their whole vibe and the music itself.”
For some, that was apparent long before their current resurgence. Gary Daly is the lead singer and co-songwriter for the English new wave band China Crisis, who worked with Becker as a producer and guitarist in the 1980s. Daly described how even in the thick of the art-damaged, authenticity-obsessed ’80s new wave scene, he and his fellow bandmates gravitated toward the Dan.
“Me and Eddie [Lundon, China Crisis co-founder and co-songwriter] were both aware of them as teenagers, we played Aja, and The Royal Scam, and Can’t Buy a Thrill … we thought we were the future, but what we were actually doing was marrying [our] kind of songwriting with the genius of Walter and the ’70s,” Daly says. “That’s why that came about—it had nothing to do with ‘are they cool or not cool anymore,’ it was like, their records are amazing, and Eddie was well aware this was an absolute triumph, putting these two things together.”
It’s slightly crude, but you could compare what China Crisis did on their stunning, massively underrated, Becker-featuring 1985 gem Flaunt the Imperfection to the most hypermodern form of “putting two things together,” and the one that’s helped bring the band back into the cultural spotlight: the meme.
@inzane_johnny, the influential Instagram meme account from noise veteran John Olson of Wolf Eyes that has more than 100,000 followers, has prominently fused their esoterica to hypermodern meme formats. Grace Spelman, cohost of The Ringer Music Show, started the “People Dancing to Steely Dan” account, which flawlessly mashes up real video of people who were very much not dancing to Steely Dan with the band’s music. A small cult quixotically obsesses over the recovery of “The Second Arrangement,” the hopelessly “lost track” seemingly requisite to any band with such a devoted following.
“When I started the account I had absolutely no idea how far it would go,” says Alex, a Brooklynite in his 30s who operates the beloved “Good Steely Dan Takes” Twitter account. (Alex requested partial anonymity.) From just a few hundred followers at its inception, the account has gone on to earn nearly 25,000 of them and a Rolling Stone interview with its creator.
“The Fagen and Becker worldview, there’s sort of this ironic stance that permeates their music, that for certain circles of Twitter is kind of like a prerequisite,” Alex says. “There are lines of theirs that almost read like tweets … ‘From keyboard man in a rock and ska band, to haulin’ boss crude in the big rigs.’ There’s just a certain similarity to the sensibility of the lyrical approach they took.”
For someone like Ky Francois of 419 Press, a 24-year-old clothing designer in Portland, Oregon, the appeal is both in sensibility and substance.
“I started collecting vinyl in college, like most people, and a friend’s mom gave me Aja, like, ‘This is something you need in your collection,’” Francois says. “I started looking at the lyrics and the meaning behind them, and I was like, there’s such a polished sound, and they’re talking about just absolute losers, you know? That, to me, was conceptually really interesting; I was like, this is crazy, these guys are geniuses.”
Francois was so inspired by Aja that he decided to stay after hours at the Portland screenprinting shop where he works and print his very own pair of custom sweatpants emblazoned in garish streetwear-chic neon with its artwork and various lyrics. After a Twitter user reposted Francois’s Instagram post featuring the one-of-one sweats and it went viral, he decided to do three runs of roughly 100 of the sweatpants, all of them selling out within hours.
“I thought I just made something really weird,” Francois says. “It took on a hypewear look, but it was about this music from the ’70s and ’80s … I just thought, ‘OK, I’ve got something really wacky for myself,’ and I didn’t realize how many other young people were interested in it as well.”
When young people become interested in the music of the past, it tends to reflect an overall trend in culture. Take, for example, the 2000s-era rehabilitation of Bruce Springsteen. The king of the wall-of-sound, heart-on-your-sleeve anthem was then still largely written off as a schlocky 1980s curio, until similarly earnest songwriters like Conor Oberst and the Arcade Fire’s Win Butler began to name-drop records like his homespun opus Nebraska in interviews. Several years later there was the transformation of Fleetwood Mac from Bill Clinton’s favorite nostalgia act to the totemic predecessors of an increasingly gender-integrated rock world (see: “You Never Knew,” the masterful Tango in the Night homage from L.A. pop-rockers Haim).
“Like, 2016 or ’17, that’s when I started to see this creep into the discourse,” says Cook-Wilson. “Steely Dan sections at record stores—I buy a lot of records—you’d start to see those empty out … it was like in the early 2010s, with a record like [Fleetwood Mac’s] Tusk, these records that Mom and Dad had in their collection you suddenly start to pay attention to.”
So, again: the generational issue. To understand why the music of Steely Dan, a band so representative of their own generation, resonates so strongly with the descendants with whom they’re supposedly at war, one might start by acknowledging that such frameworks are rarely as simple as they might seem. So when we spoke, I posed the question to Fagen: Is there a line going backward through time that transcends such a simplistic narrative, connecting today’s Dan-obsessed youth, their contemporaneous fans, and even pre-rock hipsters like Jean Shepherd, the radio host and writer beloved by Fagen in his childhood (as memorialized in a 2008 Slate essay)?
“There’s a general sense of humor that comes with a realization that what you were taught in school about American history was wrong,” Fagen says. “There was a language we heard in the media, and in articles in the ’60s, with the space race, and all that kind of stuff, there was a lot of deceit, and I think a lot of the humor was defensive toward what we realized was going on.”
“You hear that with the Beats, Ferlinghetti, and Ginsberg, and what started out as marginal humor, like Jean Shepherd and other people,” he continued. “Now, why has this suddenly become an interest of younger generations? I’m not sure, except that certainly all of that’s just gotten worse.”
In other words, as long as false optimism, self-delusion, conformism, superficiality, and all of their cousins hold sway in society, there will be Steely Dan People. That is to say, forever.
“Some things that used to seem cool now seem psychotic, and a lot of things that seemed psychotic are accepted,” Fagen says. “It may have started in the Reagan era, but when they started cutting funds for education … it changed the values of people, and they seem to be more gullible than they ever were, and they were plenty gullible when I was a kid.”
As for the peculiarly modern, extremely online form that the current era of Steely Dan fandom has taken, Fagen says he hasn’t seen much of it. I informed him of the outsized cultural space Aja and Gaucho now occupy, including Francois’s sweatpants, which earned a thoughtful-if-nonplussed grunt. But when I asked his overall thoughts about social media as a cultural engine, however—in his 2013 memoir, Eminent Hipsters, he makes numerous derisive references to the inattentive and ungrateful “TV Babies” that peppered his concert audiences—he expressed concern for the hearts and minds of the next generation of fellow-traveling, wary outsiders.
“When I was a kid, I didn’t have a lot of friends, so I was alone a lot, and I had my own interests, which were not the interests of many of my peers,” Fagen says. “Now it seems like everything is decided, whether through trolling, or stuff that’s promoted, through a madness of crowds. I think people need to be more alone, and to turn off their phone, and resign from their social media platforms, or else you don’t really find out who you are. You can’t really do it when you’re surrounded by other people.”
The ethos Fagen cultivated over all those years is best captured by one of their signature songs, whose lyrics have been immortalized maybe more than any in their discography: 1977’s “Deacon Blues,” a semi-autobiographical tale of a sad sack with similar inclinations to Becker and Fagen but who never quite hit it big. In 2015, the duo broke down the song’s origin for The Wall Street Journal:
“The protagonist in ‘Deacon Blues’ is a triple-L loser—an L-L-L Loser,” Becker said. “It’s not so much about a guy who achieves his dream but about a broken dream of a broken man living a broken life. … A mystical thing takes place and he’s suddenly aware of his surroundings and life, and starts thinking about his options. The ‘fine line’ we use in the song … is the dividing line between being a loser and winner, at least according to his own code. He’s obviously tried to cross it before, without success.”
“Say a guy is living at home at his parents’ house in suburbia,” Fagen told the WSJ. “One day, when he’s 31, he wakes up and decides he wants to change the way he struts his stuff.”
If you’re the kind of person who’s read this far into a feature about Steely Dan, you probably know that the “fine line” between a wisecracking, gimlet-eyed social critic and the morose would-have-been of “Deacon Blues” is just one shot of the scotch whiskey invoked in the song’s chorus. The enduring character of Steely Dan’s music that’s allowed it to outlast the cultural small-mindedness that once put them out of fashion, uniting everyone including, as one Twitter user put it, “trans girls and boomer dads” in shared affection, is thus: The deck is stacked against the sensitive and yearning in this world, and like a doomed member of a Coen brothers ensemble, they’re more likely than not to meet an ignominious end.
But to face that reality, absent the gullibility and deceit Fagen described to me, is its own reward (perhaps, obviously, by way of inspiring an anti-hero’s ballad as pitch-black as “Deacon Blues”).
“They were an unidealistic band at the end of a very idealistic period,” says the critic Carola Dibbell. “That unidealistic quality probably appeals to their young fans today.”
A point well taken. But “idealism” is decidedly different from having “ideals.” And if Steely Dan’s music was free of such things, it wouldn’t have the unexpected emotional resonance that pops up on something like “Any Major Dude Will Tell You,” one of their greatest songs and a rare, revealing flip side to the pity party of “Deacon Blues”:
Have you ever seen a squonk’s tears? Well, look at mine
The people on the street have all seen better times
Any major dude with half a heart surely will tell you, my friend
Any minor world that breaks apart falls together again
It’s all there: the obscure literary references, the jazz lingo, the insight to see the world’s flaws and the muted optimism to endure it anyway. Brushing aside the tweets, the irony, Tony Soprano, et al., it’s very easy to see why such a sentiment would ring true with a generation desperate for a guiding ethos in a chaotic time. As Good Steely Dan Takes once tweeted, the band “holds up better in 2020 than it did in the ’70s. We are all suburban losers dreaming of something meaningful now.”
“On one hand, it’s terrible, terrible music,” Fagen says with his characteristic wryness. “But on the other hand, the combination of the music, and the lyrics, the contrast, there’s something Brechtian about the whole project that I think is hopefully valuable.”
The comparison is apt. In a thoroughly irony-poisoned era, one can imagine the overweening saxophone solos, the crooning background singers, the purposely off-putting lyrical references, as almost necessarily provocative for younger listeners to latch on and discover the songs’ core social critique and big-heartedness.
Plenty of Steely Dan’s contemporaries attempted to deliver both, but none of them matched their sui generis, effortless cool. (As their most famous younger fan once put it: “When you try hard, that’s when you die hard.”) The Beats, Brecht, and cryptids aside, Becker and Fagen conjured that through the only real form of cross-demographic communication—simply being themselves.
“These waves have come of affection and loathing over the years. During the punk era, we took a lot of hits, saying we’re only interested in technique, or perfection, or stuff like that,” Fagen says.
“I think they thought we were the Stan Kenton of the time,” he continues, referring to the mid-century big-band leader derided by hardcore jazz fans for an empty, pompous virtuosity. “But we never felt that at all. I just thought we were making something beautiful.”
An earlier version of this piece incorrectly attributed a quote to Alex when it belonged to Good Steely Dan Takes.
Derek Robertson is a writer and critic, the digital editor for Indianapolis Monthly, and a contributing editor to Politico Magazine.