The 10 Best Steely Dan Songs

Chris Walter / Getty Images

The 10 Best Steely Dan Songs

Chris Walter / Getty Images

Steely Dan’s Gaucho turned 40 last week. Forty is the perfect anniversary for a Steely Dan album, since so many of their narrators, on that album in particular but throughout their catalog, seem to be middle-aged men bemoaning their lost youth. Which makes it all the more astonishing/horrifying that the band’s two creative voices, Donald Fagen and Walter Becker, were 24 and 22, respectively, when their first album, Can’t Buy A Thrill, was released in 1972. By the time they broke the “band” up in 1981, they were in their early thirties but seemed much older.

Steely Dan’s catalog is one of the most perverse bodies of work ever subsidized by a major record label. Their lyrics encompass sexual predation, drug addiction, murder, and every other sin imaginable, but they never judge their characters or seem like they’re showboating. They are witty, even gleeful, but ultimately dispassionate observers, speaking to each other in gnomic slang so impenetrably referential at times that it’s almost twin talk. And the stories they tell — of hipsters on the downward slide, of rueful infidelity and intergenerational angst, of people with nothing in common but their damage — are wrapped in complex and impeccable arrangements. They write songs that borrow from blues, New Orleans R&B, and a dash of Nashville, build them out of jazz chords and Latin rhythms, and throw in the occasional snarling guitar solo to keep it from going down too smoothly. Donald Fagen’s nasal, sneering voice almost gives away the game sometimes, but he’s also capable of an earnest vulnerability that can trick you into feeling sorry for the schlub whose downfall he’s laying out, one oblique couplet at a time.

Steely Dan the band (and there was one, early on) ceased to exist in 1974, so that Becker, Fagen, and their true creative partners, producer Gary Katz and engineer Roger Nichols, could really get down to work. Their classic run of albums — 1975’s Katy Lied, 1976’s The Royal Scam, 1977’s Aja, and Gaucho — were studded with legendary session players and jazz musicians including saxophonist Wayne Shorter, guitarists Larry Carlton and Lee Ritenour, keyboardist Joe Sample, bassist Chuck Rainey, and drummers Steve Gadd, Bernard Purdie, Hal Blaine, and others. The sound is warm and crisp, with each instrument precisely placed in the mix like diamonds on velvet. Echo and reverb are rare and jump out when they appear, like the treatment of Fagen’s vocals on “Black Friday” from Katy Lied.

Steely Dan’s legacy rests on their initial seven-album run; I tried to find a song from their two 21st century offerings to fit into this list, but the Becker and Fagen of 2000’s Grammy-winning Two Against Nature and 2003’s Everything Must Go had developed a smirky, Sparks-ish self-awareness, and the music had become as boring as the duo’s detractors had always accused the earlier records of being. The 10 songs below, however, are a master class in barbed lyrics, surprising but always apt instrumental choices, and immaculate but never sterile production.


"My Old School" (From Countdown To Ecstasy, 1973)

The rollicking piano and punchy horns set you up for a romp, and the lyrics — full of veiled references to Becker and Fagen’s time as students at Bard College in upstate New York — seem funny at first. But Jeff “Skunk” Baxter’s stinging lead guitar hints at the cruelty that pops up in the final verse, as Fagen sings, “California tumbles into the sea/ That’ll be the day I go back to Annandale” over Jim Hodder’s precise yet stomping backbeat. The guitar solo that takes the song out is one of the most searing in the band’s entire catalog.


"Do It Again" (From Can’t Buy A Thrill, 1972)

Steely Dan opened their debut with this track, a portrait of three losers driven by obsession to their inevitable doom, laid out over a Latin jazz groove that could have come, wind chimes and all, off a contemporaneous Santana album. The solos — electric sitar and cheap plastic organ — are pure Dan, though, as are the lyrics, which describe revenge, infidelity, and gambling addiction dispassionately, the subject always an anonymous “you” with the band themselves mentioned in the third verse as “us.” The pattern for the next six albums has been set: They’re on the inside, you’re on the outside.


"Black Friday" (From Katy Lied, 1975)

Another album opener, “Black Friday” gallops along, future Toto member and session godhead Jeff Porcaro laying down the beat with Chuck Rainey on bass and Walter Becker uncoiling some genuinely raw, noisy guitar throughout. Fagen, anchoring the track from the organ, tells a first-person story of escaping a financial apocalypse (“When Black Friday comes/ I’ll collect everything I’m owed/ And before my friends find out/ I’ll be on the road”) and running away to Australia (“Gonna do just what I please/ Gonna wear no socks and shoes/ With nothing to do but feed/ All the kangaroos”). He’s the rare Dan protagonist you actually find yourself rooting for.


"Doctor Wu" (From Katy Lied, 1975)

Doctor Wu was a real person, an acupuncturist and Chinese herbal medicine practitioner in Washington, DC. This song seems to be written from the point of view of a patient attempting to kick heroin, who eventually discovers that “Katie,” a woman who’s been helping him, is also betraying him, possibly with Doctor Wu. Alto saxophonist Phil Woods provides a fascinating counterpoint to Fagen’s crooning vocal and powerful piano; his first solo is smooth and fluid, but his second, heard as the track fades out, is fierce and has an almost free jazz intensity.


"Babylon Sisters" (From Gaucho, 1980)

Gaucho, a collection of short stories set to music, begins with a ticking, shuffling beat from Bernard Purdie, and a deep, almost dubby bassline from Chuck Rainey. Gradually, guitar and keyboards, and eventually a multitude of horns and some of the most sardonic female background vocals ever recorded, come creeping in. Fagen’s narrator describes a weekend with a woman he doesn’t respect (“Turn that jungle music down/ Just until we’re out of town”) but is still afraid of losing (“So fine, so young/ Tell me I’m the only one”). The backup singers laugh at him behind his back.


"Black Cow" (From Aja, 1977)

Fully half this list is album openers; Steely Dan really knew how to set a mood. “Black Cow” is sung from the point of view of a guy who’s tired of being his faithless semi-girlfriend’s shoulder to cry on (“I’m the one/ Who must make everything right/ Talk it out till daylight”), and it’s set to an oozing, slinky funk track with such an irresistible groove that in 1997, Lord Tariq & Peter Gunz sampled it for “Déja Vu (Uptown Baby)” — for which Becker and Fagen demanded $115,000 up front and 100% of the publishing, and got full songwriting credit on the album. They can be seen rapping to the track in this video, which is either one of the funniest or most infuriating things you’ll ever see.


"Aja" (From Aja, 1977)

“Aja” is one of the longest songs in the Steely Dan catalog — it runs a full eight minutes, and much of that is instrumental. The immaculately produced track, which has a subtle Latin groove and an almost suitelike form, is highlighted by two amazing solos, one from saxophonist Wayne Shorter and two (first behind Shorter and then again in the piece’s final minute) by drummer Steve Gadd. The lyrics are opaque even by SD standards, mostly about the narrator’s obsession with the titular woman. But it’s really about the music, which is a frankly stunning display of virtuosity that somehow never becomes dry or uninvolving.


"Kid Charlemagne" (From The Royal Scam, 1976)

“Kid Charlemagne,” which opens the band’s fifth album, tells the story of a ’60s figure based on Owsley Stanley, a San Francisco LSD chemist who also ran sound for the Grateful Dead under the name “Bear.” To Becker and Fagen, the Kid’s time has passed, not so much legally (though there’s that) but because “All the Day-Glo freaks who used to paint the face/ They’ve joined the human race”. And now nobody wants to be his friend anymore: “Clean this mess up else we’ll all end up in jail/ Those test tubes and the scale/ Just get it all out of here… I think the people down the hall/ Know who you are”. Musically, the song is slick urban funk with a fierce guitar solo from fusion ace Larry Carlton, a million miles from shambling hippie-ism and yet more proof of the band’s message: The ’60s are over. Get it all out of here.


"Peg" (From Aja, 1977)

Prominently sampled by Prince Paul on De La Soul’s “Eye Know” (Becker and Fagen were considerably more generous/less rapacious in 1989 than 1997), this is one of Steely Dan’s sunniest, most uptempo songs. It also features some of the most bizarre background vocals, courtesy of Michael McDonald, in pop music history. He’s singing individual words and phrases (“Peg,” “foreign movie”) in a manner so blatantly punched-in that he himself sounds like a sample — or, given that this was 1977, a Mellotron loop. And special mention must be made of Larry Graydon’s bizarre, rambling, bent guitar solo, which seems to have nothing to do with the song around it, but somehow fits perfectly.


"Gaucho" (From Gaucho, 1980)

This song got Becker and Fagen sued by Keith Jarrett, who claimed that its melody was plagiarized from “Long As You Know You’re Living Yours,” from his 1974 album Belonging. Fagen admitted it, and Jarrett has been credited as a co-author of the song since the ’80s. Lyrically, it’s an outlier in their catalog, as one of the few SD songs to depict a non-heterosexual relationship; as near as I can tell, a rich businessman is being embarrassed by his young boyfriend, who’s brought a fellow hustler or at least a crass, uncultured friend to some sort of upscale gathering “high in the Custerdome.” Musically, it’s a bluesy, piano-driven ballad, a shimmering smooth-jazz cloud with an insistent backbeat, over which Fagen’s narrator expresses dismay at the situation he finds himself in. “Would you care to explain?”

Listen to the playlist on Spotify:

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