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Six Definitive Songs: The ultimate beginners guide to Steely Dan


It says a lot about Steely Dan that they got their name from a William S Burroughs reference to a sex toy. It says even more that Chevy Chase was their first drummer when they were essentially a jazz band. This odd mix of an artistic literary canvas, splattered with youthful comedic irreverence and earnest musical intent has served them very well indeed. 

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In this sense, they are a refreshing musical oddity. All too often only artists with a degree of solemnity find themselves revered as though we have to be certain that someone is smart and serious enough to be worthy of praise, but Steely Dan have escaped the clutches of cursed novelty and sprung a sideways glance upon the mainstream. With this, they have influenced a wider circle than many of their contemporaries, remaining not only relevant in a musical sense but helping to colour a wider cultural realm. 

The band formed in 1971 at Bard College in Annandale-on-Hudson, New York where Walter Becker and Donald Fagan met in The Red Balloon where Becker was practising the guitar. Fagan would later recall: “I hear this guy practising, and it sounded very professional and contemporary. It sounded like, you know, like a black person, really.” He swiftly asked Becker if he’d like to form a band, and the rest, as they say, is ancient history. 

Initially, the pair bonded over a mutual love for jazz and soon they regressed to a sort of subterranean beatnik lifestyle, steadily developing the complexion of Alaskan vampires, who jammed and smoked. As their college friend, Terence Boylan would recall: “They never came out of their room, they stayed up all night. They looked like ghosts – black turtlenecks… Absolutely no activity, chain-smoking Lucky Strikes and dope.”

When college was over and they were forced out from their feted lair, the clean air of visceral rock ‘n’ roll came as quite a refreshment to them and their sound began to change. As they slowly found some success soundtracking Richard Pryor movies and being covered by Barbra Streisand, their style still somehow retained a lingering bedroom bound ethos that their unfurling career has always held the smell of. 

Below we’re looking at the six tracks that define Steely Dan best, from the early efforts of mixed-up influences to their pairing with maniacal sound obsessive producer Gary Katz and the ensuing success that is flourishing once more in the Twitter age where near-nonsensical acerbic wit sits millimetres from the glare of solemnity, in short, an ideal spot for Steely Dan to enjoy a resurgence. 

The six definitive songs of Steely Dan:

‘You Gotta Walk It Like You Talk It’

Part of the beauty of the birth pop culture is that music escaped the linear realm of merely being about melodies and opened up a whole new bohemian world. For instance, the very fact that Steely Dan contributed to a little known Peter Locke directed Richard Pryor film will be endearing enough for some fans even before you get to the groovy rhythm.

Imitating the froggy vocal styles of Randy Newman is an interesting choice, but they are a band that uphold colourful flourishes as a central tenet of their work. When Fagan was asked later why they chose to work on the film he simple declared, “We did it for the money,” how refreshing it is that even their capitalist ventures weren’t taken seriously.

‘Dirty Work’

The track ‘Dirty Work’ on their debut record Can’t Buy a Thrill begins with a plastic organ summoning the sound of some sanguine morning and the slow steady waltz of a hangover lingers in the refrains throughout. There is an almost apathetic self-loathing to the verses followed by a Big Lebowski-esque “I can’t worry about that shit, man,” exultation to the chorus. 

The beauty of Steely Dan, however, is that just about all of this is implied. On reflection, everything is far too understated to be as exacting as my own wavering interpretation, and yet many fans summon personal evocations from the track just as clearly. This typifies their post-modernist literary styling as a band, where instruments are almost prose-like in the way they come together with the narrative to inform the story of the song.

‘Rikki Don’t Lose That Number’

In a recent exploration behind the story of this song, our very own Tyler Golsen wrote: “It’s jazz. It’s always jazz. No matter how close they came to brushing up against the pop mainstream, no matter how much they leaned into the balladry of soft rock or adult contemporary, no matter how much their initial twin guitar attack was reminiscent of hard rock, and no matter how similar their lengthy instrumental excursions might have been to progressive rock, everything that misanthropic musical geniuses Steely Dan did always came back to jazz.”

Not only is it jazz, but it also begins with a sound almost akin to a whale song. In short, there is a hell of a lot in the welter of Steely Dan’s otherwise simple sound. With discordant chord changes hidden within a melody of butter cutting ease, never has simple delicious sonic fried chicken held so many secret ingredients.

‘Kid Charlemagne’

In 1963, the patent for LSD expired. There was a three-year period after that where the drug was legal and, although it seems very un-sixties-like to mention admin, it was this logistical oversight that defined an era as the kaleidoscopic headwind of acid blurred the zeitgeist in a tie-die hue of peace, love and utter psychedelic mayhem. During that time lived a man called Augustus Owsley Stanley III and with a name like that he was obviously going to wind up tripping into the scene. He is the central protagonist of ‘Kid Charlemagne’. 

As previously mentioned, their name was inspired by William S Burroughs and this track is when they most faithfully transposed his weird work into song. This wild post-counterculture reflection is as smooth as acid pop has ever been. 

‘Hey Nineteen’

After producing seven records in rapid succession in the 1970s, the 80s arrived and brought about Gaucho then a 20-year hiatus thereafter. Throughout their prolific period, the sound of Steely Dan had swayed like a drunk at the bar trying to act cool. The song ‘Hey Nineteen’ sounds like the culmination of that journey, maybe not a zenith in terms of quality, but certainly a crystalising moment of their evolution. 

Their post-modernist ‘show don’t tell’ coupling of lyrics and melody once more come to the fore. The refinement of the jazz underbelly provides a simple and sparse surface, but there is so much depth lingering in the welter that you could drop a bomb into the track and never hear it explode. In short, by this point they had cut loose so much that there was nothing left to do but cut back. 

‘Cousin Dupree’

When Steely Dan returned with Two Against Nature, their first record after 20 years apart, they were greeted with a score of 1.6 out of ten by Pitchfork. Without getting into the grading of the album, it proved defining of ‘The Dan’ in the sense that they have always been divisive, and their irreverence was open to the starker interpretation of just being daft.

Divisiveness is always a symptom of being creatively daring and it is an attitude that has helped the band defy banality throughout their career. Having the stones to launch a comeback album with a track about the titular fantasies of a perverted cousin over a melody so unassuming that the song could easily be accidentally added to an elevator playlist is emblematic of the casual bravura that makes them relevant to this day. It might not be for everyone, but it was scarcely meant to leave the doldrums of a college bedroom in the first place.