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Autumn 2014
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Books and Culture

Ian Penman
So Hip It Hurts
Steely Dan’s Donald Fagen looks back.
16 January 2014

Eminent Hipsters, by Donald Fagen (Viking, 176 pp., $26.95)

Donald Fagen in 2009
Keystone, Jean-Christophe Bott/AP Photo
Donald Fagen in 2009

In January 1974, Joni Mitchell released the exquisite, deceptively sunny Court and Spark; two months later, on the penultimate day of March, the Ramones played their first gig. The year obviously had some fine diversions and big surprises in store for the clued-up rock fan. But if you had to identify a dominant trend that year, it was huge stadiums echoing to the roar of monumentally heavy boogie. A lot of endless, finesse-free jamming. A lot of stack-heeled get-down. A job lot of stretched-thin double-live albums. A brutalized 12-bar blues without end.

Donald Fagen and Walter Becker sat uneasily in this world of earnest sentiment and antediluvian riffing. An impassively odd couple with encyclopedic jazz smarts and a glowering, gnomic mien, in some ways they sat exactly midway between Joni and the Ramones: pinup idols of the urbane Los Angeles studio scene but with bags of spiky, shades-after-midnight New York City attitude.

Dorm buddies who met at Bard College in upstate New York, Becker and Fagen started out in a band called the Bad Rock Group, with Chevy Chase, no less, on drums. They were over-literate beatniks with midnight-cafeteria tans and their own hinky, Beat-derived argot. Their second band found its name courtesy of William Burroughs: Steely Dan 111 is a garrulous sex aid, a minor player in the fizzing mind/body loop of Naked Lunch. Musically, the Dan were more jazz-inflected than rock-driven, filled out by a movable feast of session musician pals. For their debut single, they picked “Do It Again,” a baleful lament about finding nothing new under the sun. At a time when sitars played as prettily exotic signifiers of limpid bliss, they amped one up for a biting, nerve-jangled solo. At a time when Rolling Stone ran long, fawning Q & As with addled vocalists and the counterculture was sold on faux revolutionary emblems, Becker and Fagen essayed a light samba to declare that it was all bunk: “A world become one, of salads and sun? Only a fool would say that.”

Putting the hook up front, taking things easy, capering along to the prevailing ethos—none of this was the Steely Dan way. Even so, 1974’s Pretzel Logic seemed like the oddest work of an already odd career. The front cover gave little away—a monochrome shot, school of Winogrand or Arbus, of a New York street-food vendor. The title track is a surreal roadhouse blues, which switches lanes into an awed reverie on Napoleonic hubris. Other songs are gossamer light, over in a minute or two, like demos that a more popular act rejected for being too spectral, morbid, tart.

Becker and Fagen started out as songwriter hacks for hire, pale ghosts in the all-business Brill Building. “Through with Buzz,” “Charlie Freak,” “With a Gun”: a rough sketch of how hit singles might sound in some spooky alternate universe. Chart hits that got lost in a notorious park one night or missed civics class to stay in bed and read Henry Miller. As if to prove the point, Steely Dan then scored the biggest hit of their career with “Rikki Don’t Lose That Number,” a hesitant, mnemonic in-joke, strung around the card-shuffle chord changes of jazz pianist Horace Silver’s “Song for My Father.” To date, it remains the only chart smash that kicks off with an unaccompanied, 23-second marimba solo.

But the strangest confection on a strange menu may have been their retooling of Duke Ellington’s 1927 composition “East St. Louis Toodle-Oo.” It sits at the end of what we used to call Side One, as the real-life East St. Louis sits on one side of the Mississippi, facing the slightly tonier St. Louis. Ellington’s original is a lilting chameleonic vamp, perfect accompaniment for a pleasure cruise down the River Styx. It starts out mournful as recollected sin (you can see the bowed heads, the black frocks snaking behind a stately hearse), but then the dark clouds disperse and the band starts to raise everyone’s knees, as if to prove that succor and sunshine were hiding under the heart-sore funk all along. It sounds in two minds—sad and ornery, yet elegantly drunk—and ends where it began, Bubber Miley’s trumpet growling like a hungry bear.

Becker and Fagen take their own “Toodle-Oo” at a slightly brisker clip, as though they’re downing cheap champagne on a fast train home from the funeral. They usher in some unexpected guests to the wake: willowy pedal steel, gravelly wah-wah guitar, and tingling stride piano replace the two-toned horns of the original. “Toodle-Oo” II shouldn’t work, but does; shouldn’t swing, but really does. It feels deeply affectionate, not glib. Steely Dan were later sampled, in their turn, by thrusting young hip-hop acts: wheel turning round and round. Nothing on Pretzel Logic is overstressed or overplayed; it’s seriously hip but devilishly playful. “Parker’s Band” may slip in clever nods to certain Charlie Parker titles (“You’ll be groovin’ high or relaxin’ at Camarillo”), but primarily it duplicates the joy of being floored by a polyphonic bebop rush for the first time. The drums are a rising heartbeat; when a multitracked squall of saxophones blows in without warning, you may want to rise and offer your own syncopated hallelujahs.

Still, many pop/rock fans were suspicious and remain so to this day. For the doubters, Steely Dan personified the infamous Terry Southern put-down: “You’re too hip, baby! I just can’t carry you.” Even Dan fans started to read the work as if it was one big put-on—a prophylactic, perhaps, against the real pain and melancholy that some of these songs contained. Maybe all along, it was the audience that was too hip, not the band; there was definitely a stripe of intellectual snobbery among would-be acolytes like my teenage self. Other spoiled rock superstars maybe “didn’t give a fuck about anyone else” (in the words of “Show Biz Kids”) because they were empty-headed snots; if Becker and Fagen also didn’t, we Dan fans agreed, it was coming from a far better, or at least a wiser, place—or maybe a far crueler place.

Some of this cognitive dissonance may be attributable to the fact that the more critics fawned over Steely Dan, the more the duo responded with markedly blasé gratitude. It may also be due to the palette they were drawing on—precedents such as Broadway theater, soundtrack scoring, West Coast jazz. These were traditions in which a big production number didn’t necessarily mean what it said; smiling major chords disclosed drooling wolf fangs; and a desolate blues prepared the soil for subsequent flags of triumph. It’s hipness of a different order—tone and texture matter as much as, if not more than, what is explicitly said or sung. (In an early interview, Fagen claimed that he was amazed that anyone liked his singing at all, when it sounded, he averred, like a “Jewish Bryan Ferry.”) The Dan’s variety of minor-chord legerdemain went against the prevailing mid-seventies grain, an ethos where every precious singer-songwriter word was presumed to be heartfelt.

But then, Steely Dan went against the grain in a number of ways. They relocated to Los Angeles in pursuit of superior recording technology, but they didn’t really fit the local scene. In a press shot for 1980’s Gaucho, the duo look like creatures just emerged from a long and difficult hibernation; their flesh has the same gray, drained plasma hue as the bony hands of the album’s cover art. Becker could be a backstreet physician, on the lam in a cheap hippie wig; Fagen looks like the anorexic, smart-ass kid brother of Jeff Goldblum’s Fly guy. Rumors began to surface of Steely Dan giving Fleetwood Mac a run for their per diem, as far as deepwater dysfunction and high-end narcotics. The difference was that the Dan’s decadence felt more oblique and therefore more tantalizing—these were chord-progression wonks, not boogie ogres! There was an added frisson in the idea of these two cerebral New Yorkers adrift in scented-candle lotusland, like a modern-day Bird and Prez. Soon enough, they did both crash and burn, in discrete ways, and a long sabbatical followed. They packed up and left Los Angeles. Becker negotiated a divorce from his five-fathom drug habit in sunny Hawaii. Fagen returned to New York and, by his own account, embraced a long-postponed, full-bore breakdown.

There was never any point when Dan devotees felt: here are two guys who might open up and let us in on the odd-couple arrangement, all the extracurricular accidents and emergencies. They were never at the top of any list you’d draw up of people who would one day pen heartfelt memoirs about their lives in music. And while I can’t see it getting an approving Oprah sticker, the big surprise about Eminent Hipsters is that it turns out to be, after a fashion, just that: Donald Fagen’s heartfelt memoir. Sure, he hides the fact behind a spunkily disingenuous “it just fell together” introductory gloss, but it’s still more flesh-and-blood affecting than even the craziest Dan watcher might have dreamed. This being Donald Fagen, he doesn’t come right out and solicit for big redemptive group hugs; the more tender lines are well hidden behind his deceptively offhand writing style. The first half is a suite of essays rooted in the late fifties and early sixties concerning “artists whose origins lay outside the mainstream”: forgotten singers, arrangers, sci-fi crazies, ahead-of-the-curve DJs, and tastemakers. This brief takes in the overlooked Boswell Sisters; the underpraised—and arguably overdemonized—Ike Turner; and the quietly influential real-life nightfly DJs Mort Fega and Jean Shepherd. Fagen also offers a few personal reflections on his late teenage years. The second half, “With the Dukes of September,” is a diary he kept in 2010 while touring with Boz Scaggs and Michael McDonald.

While the essays present a fascinating prospect, the tour diary looks like it might be a bad goof, a parody of old-time rock-star self-indulgence. Who needs it, even from one-half of Steely Dan? Do we want cool guys to spill? Doesn’t our fascination rest precisely on their flinty, recessive nature? But “With the Dukes” turns out to be one of the laugh-out-loud funniest things anyone ever penned about the workaday woes of being a pro musician. It’s such outrageous fun, in fact, that it threatens to overshadow the less showy virtues of the essays. Structurally, the book doesn’t quite hang together: it feels like two different pitches jammed together to make one awkward hybrid. If Eminent Hipsters were a film, you can imagine a weave of the two strands: jaded, lost-in-America Donald has a series of flashback reveries while spaced out along the tour, recalling just how it was that young Donny got here and who inspired him to light out this way.

There are moments when, exploring twenty-first-century America, Fagen has cause both to revisit his own checkered past and reevaluate some of his heroes. There’s a mildly tragicomic episode where Fagen realizes that he is to play a local auditorium named after Count Basie. His mood brightens—and then darkens after he realizes that none of the audience seem to know, or care, who this blow-in foreigner Count Basie is, anyway. Fagen doesn’t belabor the point, but it might be a good topic for a social studies class: What is the point of civic commemoration if you’re commemorating a blank? Eminent Hipsters may itself be Fagen’s way of throwing a greasy spanner into the works, at a moment when Steely Dan seem to be settling nicely into rock’s own nostalgic industry. Fagen scans the American hinterland and wonders what he’s doing and whether a creaking, picky New York homebody should be doing it at all at his age. Do the “TV babies,” as he calls younger consumers (a phrase out of Allen Ginsberg via Gus Van Sant’s 1989 Drugstore Cowboy), even know why he’s honoring the old R & B pioneers whose ghosts he calls up nightly? Has the public conversation gone stone-cold dead?

Fagen doesn’t want to come across like one of those testy old cranks who get aggrievedly reactionary with age (“Hobbesian geezers”—a nice bit of phrase making), but he doesn’t want to kid himself that all is right with the world, either. What he wants is some kind of safe, hallowed, but still-testing middle ground. He recalls the often derided era of the early sixties as a time with its own sense of verve, jest, and decorum. Of that era’s TV: “lots of swell black-and-white movies from the thirties and forties, all day and most of the night. No soul-deadening porn or violence. Decent news programs and casual entertainment featuring intelligent, charming celebrities like Steve Allen, Groucho Marx, Jack Paar, Jack Benny, Rod Serling, and Ernie Kovacs.” (So far, there have been no signs of a reality TV series in which Becker and Fagen audition session musicians for a new album and tour.) And for a flinty old cynic, he can be suasively rhapsodic: “And I’ll start thinking about a late summer sun setting over fifteen hundred identical rooftops and my family and bop glasses and Holly Golightly, about being lonesome out there in America and how that swank music connected up with so many things.”

It’s a portrait of the artist as an embryonic Florida retiree: grumpy, fidgety, fond (his hotel room iPod plays nothing but old Verve jazz or Stravinsky), ungrateful toward fans, snarling at managers, leering at young poolside babes, spiteful to hotel staff. Fagen doesn’t skirt the risk of deep mortification. He leads us round 360 degrees of his touring profile: petty, grouchy, backward-looking, too smug by half. And yet, while it appears to be an entirely truthful account, all the time part of me was thinking: Is this actually the equivalent of a well-crafted Steely Dan character? “Deacon Blues” on Prozac? As I said to a friend and fellow Dan obsessive, Eminent Hipsters is essentially On the Road with Alvy Singer. In Woody Allen’s Annie Hall (1977), his OCD doppelgänger Singer loathes Los Angeles, but work and romance install him there for months at a time. Allen initially wanted to name his feel-good film after a bleak psychiatric diagnosis: anhedonia, a condition that also seems to cover how Fagen now feels about touring: “The inability to experience pleasure from activities usually found enjoyable.” Like Allen, Fagen seems deeply versed in the language of shrinks and footnotes from the Physicians’ Desk Reference. In the missing years between The Nightfly and resumption of his partnership with Becker, Fagen had a real Freudian schlep of therapy, and much (legal) pharmaceutical rewiring. While you still wouldn’t call him a little ray of sunshine, these efforts seem to have done a lot to revamp his subsequent life: marriage, uninterrupted work, a relative cessation of hostilities with the media. While the other Donald might conceivably have written a tour diary, you can’t imagine he would have allowed it to be published.

Today, when we identify a hipster, it carries entirely different connotations from the word’s original, darkly lustrous charge. “Hipster” is now a slight, because hipsters now are slight—not so much a soulful tribe as a fly-eyed pose looking for somewhere to land. Hipsters move into your locale, and before you know it, brittle quotation marks are strung everywhere. Hipsters have become little more than an advance guard for the arcadia of “hip capitalism.” Once, though, it truly mattered how hip you were. In Fagen’s day, things were different. Born in 1948, he belongs to a baby-boomer generation for whom the benediction of hip was most devoutly to be desired. It was a dark and uncertain thing, an arduous rite of passage, almost a spiritual gamble. Lewis MacAdams, in his 2001 overview, Birth of the Cool: Beat, Bebop, and the American Avant-Garde, recalls how New York bohemian Judith Malina (later cofounder of the Living Theatre) found herself briefly jailed following a mid-Manhattan protest march. A nice middle-class girl under it all, she’s shocked to find herself sharing space with honest-to-goodness streetwalkers. “I like you,” declaims one prisoner to Malina, “but let’s face it. You’re a square.” MacAdams supplies a subtle but powerful sense of where hip’s true cargo originates. If it’s at street level, the street is on the other side of town. Hip was, most of all, a black phenomenon, “cool in its slavery-born sense, where attitude and stance is the only self-defense against overwhelming rage.”

New York was the seedbed of hip: Harlem’s Apollo, Birdland, the Cedar Tavern, the Village Voice. Hipness was arcane. If you had to ask, you were nowhere. MacAdams: “Everything had to be understated, circuitous, metaphorical, communicated in code.” It was a time when drugs of any kind, interracial dalliance, homosexual love, could all earn you serious jail time. Then, as the sixties loomed, hip crawled into the mainstream light: it began to be discussed, analyzed, advertised. A lot of blame should probably be placed at Norman Mailer’s door. True hipsters would let slip one pithy phrase or exit inside a ringing Zen ellipsis; Mailer blathered on at great length and made hipsterism seem verbose, fraudulent, a cheap thrill for bored socialites. He missed the unmissable point, which was: never explain or sermonize. There was an art to betraying nothing in public—not anger or fear, approval or approbation. Cool manners were a shield for those who were allowed few weapons of self-defense, a ghetto hijack of Kipling’s “If you can keep your head when all about you are losing theirs,” both mask and recompense for folks who had a justified feeling that all sweet ideological promises tended to leave them in the same hole, holding the sharp end of the stick.

Fagen’s roll call of hipsterdom doesn’t promote some overfamiliar cast of scurvy Beats and angry savants, bemoaning the plastic tragedy of conformist Amerikkka. Fagen likes plastic. He digs people who straddle the divide between hep and square, margin and MOR, a no-man’s zone where apparent squares take on the prompts of hip and parlay them into a wider audience. “The concept of hip had exploded into the culture in a new manifestation.” Fagen is very good on artists from that time (Basie and Ellington, Erroll Garner, Billy Eckstine, and Sarah Vaughan) who, abandoned by the hipster cognoscenti, worked their way into less cool but far more secure and remunerative positions. Most were in the early autumn of long careers, and while they weren’t up for stretching any more boundaries, they could still knock out work of devastating economy and depth. Fagen’s paradigm is not the supposedly world-changing works like Howl or On the Road, Ornette Coleman’s Free Jazz, or Stanley Kubrick’s Dr. Strangelove—it’s concertedly in-between stuff, bronchial guys in airless studios fussing over augmented chord progressions. Fagen is lyrical about his idol Ray Charles—hobbled by racism, blindness, and addiction, but a canny operator who smooched the mainstream with roughed-up textures, surprising combinations, dissimulated taunts. In another lovely tribute, “Henry Mancini’s Anomie Deluxe,” Fagen explains how the eponymous arranger used jazz idioms and jazz players in his TV and film work. “He utilized the unconventional, spare instrumentation associated with the cool school: French horns, vibraphone, electric guitar and—Mancini’s specialty—a very active flute section, including both alto flute and the rarely used bass flute. Instruments were often individually miked to bring out the detail. . . . There was a lot of empty space. It was real cool.” Mancini gave a bop edge to such TV bagatelles as Peter Gunn and Mr. Lucky, just as Quincy Jones would later score Ironside and pianist Lalo Schifrin would rework the unforgettable Man from U.N.C.L.E. theme. (Both Schifrin and Jones were graduates of the Dizzy Gillespie touring band, and Jones was mentored early on by Ray Charles.) Mancini titles such as “Dreamsville” and “A Profound Gass” (sic) inspired Fagen to learn more about jazz, and “out of these fragments of hip and hype I constructed in my mind a kind of Disneyland of Cool.” For a moment, we’re dropped into the adolescent Donald’s reverie about a Mancini recording session: “Everybody’s smoking Pall Malls or some other powerful nonfilter cigarettes. Hank hands out the parts. When they run down the chart, a thick membrane of sound flows forth and hovers in the room. It sounds incredibly plush.” It’s rare to read a musician who writes well about the recording process.

Shelves of books are devoted to unearthing the fugitive “meaning” of pretty song lyrics, yet often it’s some forgotten scrap of melody that cracks us apart; an old sitcom theme from decades ago can deep-six us more effectively than most big-name, chart-topping tracks. Becker and Fagen knew all about the occult effectiveness of tone and texture. The more studio time they could afford, the more they explored this world of sonic spacing, layering, and counterpoint. Across Aja and Gaucho and Fagen’s own Nightfly, musical grain counts as much as buffed-up words. Listen again to “Black Cow” from Aja: a moony relationship, bogged down in slackness and routine. Recrimination rears its snapping-turtle head, and breakup is surely imminent: “I can’t cry any more.” The rhythm uncurls like someone under deep anesthetic. Plod, plod, plod, through a big black cloud. Then (“just when it seems so clear”) we turn a corner and the music perks up, becomes almost punch-the-sky joyous, a homecoming parade of high-five bass and pungent roadhouse sax.

Or try “New Frontier” from The Nightfly, which opens with an ear-popping surge of forward motion. Drums skip and skim like speedboats leaving a summer jetty; the electric piano nudges you with a conspiratorial grin. The chorus rises and falls like sun motes on a holiday balcony. But there’s something else here, under all the mist and spray—a strange hesitant guitar fill, like a nagging second thought, fussing away throughout the song. The major-chord whole is so effervescent and pulls you along in such a happy trance that it’s only in retrospect that you realize what a difficult balancing act Fagen pulls off. In “New Frontier,” he distills the secret fears slumbering under the aquamarine repose of hot summertime fun. Fagen sounds upbeat, like a Supremes 45, but “the key word is survival on the new frontier.” Take that how you will. In isolation, it has a ring of tooth-and-claw realpolitik. But survival is living, too, and in the end, “New Frontier” is a low-down limbo shimmy, celebrating a new-dawn limbo time.

The song’s title is an uncharacteristically candid reference to an antecedent text: John F. Kennedy’s speech accepting his presidential nomination at the 1960 Democratic convention. The onset of the decade ahead: Camelot dawning, and Kennedy eternally young and forever tan in blinky monochrome footage. When the women behind him applaud, all you can see is a blur of white dress gloves. The New Frontier was a tiny nugget phrase that set free outsize reverberations. From “IGY,” which launches The Nightfly: “Standing tough under stars and stripes / We can tell: this dream’s in sight.” But consult the speech in question, and you find that it has a surprisingly ashy Cold War taste. Rather than the expected sound-barrier boom of celebration, the message is more like: ignore this advice at your peril. The speech’s rhetorical march falls on a series of hesitant downbeats: “unknown,” “unfilled,” “uncharted,” “unsolved,” “unconquered,” “unanswered.” It’s full of pinched undertones, as much provocation as celebration. Are you up to the trek ahead? Have you got the bright stuff? Do you relish the idea of uncharted space, unfilled time? As much as he was looking forward, celebrating American know-how and optimism, Kennedy was also speaking against unacknowledged failings: prejudice, poverty, everything that held the American Dream out of reach for many sections of postwar U.S. society. On the page, if you Magic-Marker those via-negativa unwords, it looks like the grand bummer of all New Tomorrow speeches, and a less capable speaker might have stumbled and missed his moment. (JFK had a rather nasal, whiny voice, but boy, he could deliver a lyric. He was the Bob Dylan of sixties political oratory.)

Fagen’s original hipster era is now as old-world distant and faraway as a Victorian player piano or, indeed, the urtext that Fagen swipes his own title from: Lytton Strachey’s 1918 study, Eminent Victorians. Strachey caused a big stir with his discreetly anti-hagiographical work, but he saw this slim volume as a resource as much for future readers as for his own contemporaries. Lytton was a bit of a proto-hipster himself—beardy, polysexual, equally at home with Maynard Keynes or sheaves of fussy French Symbolist poetry. Where Strachey was out to puncture received wisdom about the era in question, Fagen wants to rescue a misunderstood time. Just possibly, Fagen has something similar in mind to Strachey’s idea of a biographical time capsule—he may be writing against his time, as much as for it. (The diary form is a useful means of raising serious concerns in a deceptively airy manner.) Looked at in this way, the essays seem less of an ad-hoc grab bag. A quick glimpse at the table of contents may suggest that Fagen’s essay choices are flagrantly, even perversely, personal; but they add up to an overview of a specific historical moment. As MacAdams puts it in Birth of the Cool: “Before, there had been many individual acts of cool. Now Cool—a way, a stance, a knowledge—was born.” Previously, what was hip had been the preserve of certain underground cliques, signaling among themselves in the darkness. Most of all, black American culture in general and jazz culture in particular were the choppy currents that fed into societal sea change.

Hip now found itself working backup for—not the Man exactly, but close enough. Fagen is spot-on identifying hip’s undercover dispersal through phenomena like TV cop shows, the film version of Breakfast at Tiffany’s, and Sinatra’s pals in the Rat Pack. Here were “street-wise swingers” who were palpably hip, “but they could operate in the straight world with existential efficiency.” This birthed a tradition of what you might call “straight hip,” exemplified by the one guy Lalo Schifrin worked for more than anyone else: Clint Eastwood. Starting with his own nightfly DJ character in Play Misty for Me, through the imperturbably cool (and sharply dressed) Harry Callahan, Eastwood embedded discreetly hip tones in precariously conservative settings, right up to Bird, his controversial 1988 biopic of original hipster Charlie Parker. Perhaps none of this should surprise us. The conventional wisdom about the success of something like Mad Men is that it plays to our cloudy nostalgia for a time before political correctness and the culture wars, a time when we were positively encouraged to smoke and exist on a diet of highballs, one-night stands, and diet pills. Everything free and easy, no constant checking of guidelines (and e-mails).

But isn’t this nostalgia less for a lax, ring-a-ding time than for a lost grid, where every moral choice was mapped out? Where everyone accepted the existence of common rules? After all, frontiers are places where things end as well as begin. It’s all about a pleasurable tension between strict rules and raised-eyebrow rule breaking. Think of Eastwood as Callahan. He’s got swell loafers and perfect shades, but he’s thin red line to the core. He swings—but not in front of the children, or on the streets, or for public consumption. I suspect that in decades to come, people will be absolutely baffled by the high-color moral variegation of the Dirty Harry series.

Rule breaking is only worthwhile when the rules you break have real meaning. Fagen is funny but acute on that moment in our teenage years when we snub parents and dismiss all authority figures but simultaneously initiate a desperate search for persuasively hep figures, people to tell us exactly what we should listen to, view, and read. What to dig. The mainstream culture of that early-sixties era may get a bad rap for being queasily paternalistic, but sometimes we need experts to teach us the art of making fine distinctions and keeping valuable traditions alive. Our twenty-first-century snake-oil promise of “more choice” often devolves into homogeneous slop, a moraine of thin and stony repetition. In the current YouTube moment, we’re told that we have a limitless look-see option on everything there ever was, laid out right before us—but at the price, perhaps, of a complete absence of critical chiaroscuro. Look up Steely Dan’s wistful “Hey Nineteen” on Wikipedia, and you find: “See also: Age disparity in sexual relationships.” Which is nearly straight-faced inapt enough to be a Becker-Fagen in-joke.

Hipsters these days have to use all their desperate wiles just to stay one step ahead of the local TV news; but back in Fagen’s youth, sources of alternative info were next to zero. It’s easy to sneer at the old idea of “in the know” hepcats, but hipsters once really were those who lit out for terra incognita. I have deeply ambivalent feelings about the over-canonized Beats, but it’s easy to forget the reason they were elected figureheads in the first place: they sallied forth into the unknown and set about indexing the whole of American dreaming, not just a few choice, sanitized cuts. Some of their takes on black culture may now strike us as risible and patronizing, and some of the quasi-religious holy-fool sub-notes feel a bit self-hypnotized (and on, and on); but at the time, they were navigating wholly without maps.

There are times on his grand tour of the U.S. in 2010 when Fagen wonders if a whole lot has changed over the preceding 50 years. There may be a black president, but whole swaths of culture are in danger of being reforgotten, belittled, or neutered in divisive “culture wars” (with errors of taste and scale on both sides). He’s alternately combative and perplexed: a 63-year-old singing the golden notes of his youth and struggling to work out if they still mean anything—if any songs do. Suddenly, hip seems less like a faded hobbyhorse for a middle-aged malcontent and more like a lively topos. In the end, Fagen is hip enough to know that you can’t run from your own adult quandaries. There are deeply affecting passages here about family and marriage, loss and aging—things the younger Donald might not have copped to: difficult negotiations, real blues. When you’ve spent your life using Cool to hold an untidy, insensate world at bay, how do you manage the rough stuff when it rears up and blindsides you on the street where you live, one fine day?

He’s good on his parents—both “the father thing” and a mother who was a more than capable lounge singer, far more creative than she let on (and thus emblematic of many women from that era with curtailed dreams). Fagen senior was someone who sincerely believed in the promise of the American Dream but found himself knocked to the canvas by real economic jabs. There was the rhetorical fandango of JFK’s New Frontier, and then there was how it played out in workplaces, bank accounts, and parental bedrooms. Also, you begin to see where the askew texture of Steely Dan lyrics may have found some of its everyday inspiration: his parents lived in a “nightmarishly bland apartment, which was in a high-rise building on—wait for it—Chagrin Boulevard.” Finally, Fagen’s hipster is not what Anita Brookner, in a lovely spearing of Baudelaire, called a Propagandist of the Pauvre Moi. What’s revealing about the scattered reflections in Eminent Hipsters is that, in the end, the claim that Fagen makes for these marginal eminences is that they were good people. Good for art, good for the social fabric, good examples for one and all.

In those long-gone, fake-ID years, the other Donald longed to be a night-blessed pulp-fiction character with a cynical blonde on his arm and big thoughts in his nodding head. “That shape is my shade / There where I used to stand.” Well, he got his dream. In the same way Bob Dylan slowly became one of those gravel-voiced old troubadours he started out imitating, Fagen is now a prickly old jazzer, languid and bittersweet. Still on the road, still making for the border, still so hip it hurts. Next March, it will be 40 years since Pretzel Logic: the same interval as between Ellington’s merciful “Toodle-Oo” and the Dan’s own fizzing but seemly tribute. Some frontiers never grow old.

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