Steely Dan: 10 Essential Songs

Leave it to Steely Dan to sound nonplussed about the song they’re maybe best known for. “It’s dumb but effective,” Donald Fagen told Rolling Stone in 2009 of the Can’t Buy a Thrill Single. “It’s no fun,” Walter Becker added, compounding the chill in the room. Still the track is a prime early example of what would become the Dan’s trademark vibe, marrying a sardonic kiss-off to an ex (“The weekend at the college didn’t turn out like you planned”) to a bouncy shuffle groove and adding on some white-hot guitar dazzlement courtesy of Elliott Randall to bring the whole thing home.

Becker and Fagen settled an old score with this rollicking rock-meets-R&B tune, inspired by a pot bust from their Bard College days that still left a bad taste with the two budding stars. “California tumbles into the sea/That’ll be the day I go back to Annandale,” Fagen sings ruefully of the institution’s upstate locale, as a perfectly orchestrated horn line tumbles down behind him.

In classic Steely Dan fashion, the duo lifted a vamp from a classic Blue Note side – Horace Silver’s “Song for My Father” – to kick off this snide account of a college romance that never was. As Fagen told it, he took a shot at seducing the then–married and pregnant Bard schoolmate Rikki Ducornet, but she never called. Like most Steely Dan love songs, this one comes with a twist of the knife: “You tell yourself you’re not my kind/But you don’t even know your mind.”

Drawing inspiration from the gold crash of 1869, Becker and Fagen portrayed a financial meltdown as an excuse for end-of-the-world revelry on this driving, devil-may-care Katy Lied opener. “Gonna do just what I please,” the typically deluded narrator vows. “Gonna wear no socks and shoes/With nothing to do but feed/All the kangaroos.”

Steely Dan led off their hardest-hitting album, The Royal Scam, with this supremely funky chronicle of the rise and fall of a countercultural legend, inspired by famed acid cooker Owsley Stanley III. “I think he was based on the idea of the outlaw-acid-chef of the ’60s who had essentially outlived the social context of his specialty but of course he was still an outlaw,” Becker once said of the song. Larry Carlton’s consummately stylish guitar solo would become mythic among the band’s muso fans, while Kanye West prevailed upon the band via handwritten letter for permission to sample the song in 2007’s “Champion.”

We can’t help but mistrust the narrator of this snazzy funk tune, who seems to be making promises to an aspiring starlet that may or may not turn out to be bunk – a classic Steely Dan theme. “And when you smile for the camera,” Fagen sings. “I know they’re gonna love it.” The pair worked their studio recruits to the bone trying to achieve this Aja standout’s consummately breezy groove, famously veto-ing a series of guitar hotshots’ passes at the solo, before settling on a gem of a lead from Jay Graydon.

In one of their more tender odes to middle-class pretension, Fagen and Becker pay tribute here to a dude from the suburbs who’s dreaming of the freer, edgier life he might enjoy if he could only learn to play the saxophone. “The protagonist is not a musician,” Becker explained in the Classic Albums doc on Aja. “He just sort of imagines that that would be one of the mythic forms of loserdom to which he might aspire. And who’s to say that he’s not right in a thing like that?” In the same doc, Fagen called the song “about as close to autobiography as our tunes get,” maybe alluding to the way he and Becker had idolized jazz musicians when they were still suburban kids dreaming of escape. The Dan imagined the title as a sort of mascot for the would-be down and out: “If a college football team like the University of Alabama could have a grandiose name like the ‘Crimson Tide’ the nerds and losers should be entitled to a grandiose name as well,” Fagen once explained.

The perfect opener to Gaucho, the final album of the Dan’s initial run and the one that represented the peak of their studio perfectionism, “Babylon Sisters” might be the band’s single sleaziest song – not to mention their saddest. Our protagonist drives “west on Sunset” with a pair of hookers, chasing a dream of youthful Cali excess he knows is fading but can’t give up. “Well, I should know by now that it’s just a spasm,” Fagen sings over the song’s buttery-smooth lite-jazz groove, though it’s clear that the narrator’s midlife crisis might just be the death of him.

Gaucho is essentially a concept record about staying too long at the fair, and this track is its skeevy centerpiece. Steely Dan protagonists don’t come much more hilariously pathetic than the aging dude from this leisurely funk tune, who’s putting the moves on a 19-year-old. He brags about his frat exploits and tries to set the mood with some Aretha, only to find that his companion “don’t remember the Queen of Soul.” The song builds to perhaps the ultimate yacht-rock refrain, which many singing it back to the band live don’t seem to realize is pure satire: “The Cuervo Gold/The fine Colombian/Make tonight a wonderful thing.”

Becker and Fagen may have been all grown up when they returned with their multi-Grammy-winning 2000 comeback album, Two Against Nature, but they still couldn’t keep their minds out of the gutter. Case in point: this tale of a deadbeat dude’s futile attempts to seduce his younger cousin. As always, their portrayal of misguided middle-age lust was creepily spot-on: “Honey how you’ve grown/Like a rose/Well, we used to play/When we were three/How about a kiss for your cousin Dupree?” The song would later lead to a bizarre flap with Owen Wilson, when the pair claimed – facetiously or not, it was hard to say – that the premise for his 2006 movie You, Me and Dupree was lifted from the tune.