Indie

The Best Steely Dan Songs, Ranked

One of the strangest (and most heartwarming) developments in recent years is the hip-ification of 1970s snarky jazz-rock institution Steely Dan. Once the butt of endless “graying ponytail” jokes by insufferable indie dweebs, Steely Dan has somehow become part of the indie dweeb canon, a turn confirmed by numerous indie music sites writing thoughtfully and enthusiastically about the band’s nine studio albums released over the course of 31 years.

Some have claimed that this embrace of The Dan is “revisionism,” but that’s not exactly right. In the ’70s, Steely Dan was widely regarded as one of the top American bands of the era. They were commercially successful and critically acclaimed. It’s just that subsequent generations for decades didn’t seek them out like they did Fleetwood Mac or even The Eagles. This was partly a function of how Steely Dan songs work — a spotless veneer of impeccable musicianship and complex music progressions act as a kind of slow release capsule for the humor and perversity that lurks inside. The whole point of this band is to grab the ear immediately, but not reveal what is actually going on until many listens, and even many decades, later. That’s not revisionism; that’s just taking a very long time to “get it.”

You might not get this band, either. If that’s the case, I’m sure I’m not the first 43-year-old straight white man to try to talk you into digging The Dan. (Though it should be noted that, contrary to some popular opinions, I know many women who love Steely Dan. I even once dated a woman who said she was looking for “a Donald Fagen type.” We broke up after only a few months, which tells me I’m more of a Walter Becker.) However, I feel like this list of my 50 favorite Steely Dan songs does make a convincing case for their greatness.

So, let’s enjoy the Cuervo Gold and the fine Colombian and experience The Dan together!

50. “Cousin Dupree”

Like many people who love Steely Dan, I once hated Steely Dan. In my mind, they were the epitome of smug, laidback, and exceedingly lame boomer music. Which of course explained why their comeback LP, Two Against Nature, won Album Of The Year at the 2001 Grammys, beating out young turks like Radiohead and Eminem. At the time, I despised this, because I was 23 years old and therefore didn’t know much of anything about anything. But now it’s 20 years later, and I’m washed, and I absolutely love Two Against Nature — not as much as Kid A, sure, but the perversity of Steely Dan winning an Album Of The Year Grammy in 2001 is a perfect choice that ultimately honors the profound perversity of The Dan. Eminem captured the zeitgeist at the time, but nothing on The Marshall Mathers LP is as gross or as brilliant as “Cousin Dupree,” a smooth-jazz tune about having sex with a family member. I am confident that no smooth-jazz songs about having sex with a family member have appeared on any other Album Of The Year winners. That is the essence Steely Dan’s genius – they trick you into initially thinking that you’re cooler than what you are hearing, when in fact their songs are subversive in ways you can’t really grasp until decades later. In the end, The Dan always owns.

49. “The Royal Scam”

The weakest Steely Dan album is the last one, Everything Must Go, which came out after Two Against Nature in 2003. It’s the one album that doesn’t have any tracks on this list. That’s not a criticism of Everything Must Go; in fact, it probably means that Everything Must Go will eventually be my favorite Steely Dan record. (I repeat: In the end, The Dan always owns.) This is a band with remarkable quality control — their pre-hiatus, seven-album run in the 1970s is one of the best in rock history. No record in that series is less than excellent, which means that every record from that time has either been my favorite or my least favorite at some point. The Royal Scam is currently right behind Gaucho and Aja on my personal list, though on some days it is absolutely no. 1. By Steely Dan standards, it is their “hardest” record in terms of sound and themes, an absolutely gutting portrait of America in decline post-Watergate. Take the title track, a song about Puerto Rican immigrants who realize the “scam” of the American Dream. “While the memory of their southern sky was clouded by / a savage winter / every patron saint hung on the wall / shared the room with twenty sinners.”

48. “Throw Back The Little Ones”

I understand that people who don’t like Steely Dan have heard the same sales pitch over and over — they’re actually bleaker and edgier than any punk band! I happen to think that is true, but also recognize that this argument is undermined by the willful inscrutability of their lyrics. For years, based on the chorus, I assumed “Throw Back The Little Ones” was a commentary on how poor and disadvantaged people are cast aside in mainstream America. But upon closer examination of the lyrics, it appears to actually be about a suburban kid who ventures downtown in search of music and adventure while attempting to conceal his white-bread background. I suppose the actual actual point is that the song is purposely opaque enough (while also seeming extremely specific) to work on both levels. After all, you can just choose to listen to the sick guitar solo.

47. “Daddy Don’t Live In That New York City No More”

The guy who played that solo on “Throw Back The Little Ones” is Elliott Randall, one of the great yacht-rock sideman. Steely Dan became synonymous in the ’70s with stacking up celebrated session guitarists like thick bricks of Acapulco Gold, a process that really started to take hold around the time of Katy Lied. Another track on that album, “Daddy Don’t Live In That New York City No More,” features some frisky rhythm work by Larry Carlton, who will resurface again throughout this list.

46. “FM (No Static At All)”

This was the theme song for a largely forgotten 1978 film about a successful LA rock radio station produced by the band’s manager Irving Azoff, the pint-sized tyrant who also worked for The Eagles and Jimmy Buffett, among other artists adored by 65-year-old men who tuck their T-shirts into their cargo shorts. Before Azoff, they “were ready to go blissfully through life without a manager,” Fagen told Rolling Stone’s Cameron Crowe in 1977. But the association with the uber-insider Azoff helped to put Steely Dan on a different level, transforming them from a cult act with a few fluke hits into one of the foundational bands of late ’70s superstar El Lay rock culture. But even then they couldn’t help but be snarky about their peers.

“We were supposed to go to The Eagles’ wedding,” Fagen deadpanned in a 1977 interview.

“No, that wasn’t The Eagles’ wedding, it was Jimmy Buffett’s wedding,” Becker countered.

“Or birthday party,” Fagen sighed.

45. “Sign In Stranger”

All interviews with Fagen and Becker are like that — two very smart and very sarcastic friends bantering back and forth, in a manner suggesting only faint interest in whether the journalist involved can keep up. It seems as though their songwriting partnership also worked that way. “The fact is, I can’t finish a song and Walter can’t start one,” Fagen once explained. Working from these limitations, they complemented each other perfectly — if Fagen became overly preoccupied with making everything perfect, Becker would keep pushing for ambiguity and loose ends. It also seems that Becker is the one who stumped for the obscure, funny asides that dot and frequently make Steely Dan songs. Like in “Sign In Stranger,” the mafia underworld snapshot from The Royal Scam, which includes references to Mizar Five, Turkish union dues, and the nightclub performer who people line up around the block to see “do the can-can-Jacques.”

44. “Charlie Freak”

In the late ’70s, Irving Azoff was merely trying to get Fagen and Becker to socialize more with other rock stars. But out in California, the Steelies felt like even bigger outcasts than they had in New York City, as two misanthropic jazzbos trying to fake it as pop songwriters. Even as they meditated on the seedy side of Los Angeles party life, they would swear up and down in interviews that they rarely left their homes, ensuring that their East Coast paleness would never take on a left coast bronze. This separation also preserved their connection to outsiders personified by songs like “Charlie Freak,” a parable about a man who buys a gold ring from a panhandler, and then learns that the destitute Charlie took that money and overdosed. It’s hard to imagine The Eagles or Fleetwood Mac writing about that.

43. “Home At Last”

Here’s another thing I didn’t appreciate about Steely Dan when I heard their cyanide-muzak hits on classic rock radio as a kid — musicianship. How could I understand Bernard Purdie laying down his trademark Purdie shuffle on “Home At Last” when I was too busy listening to Rancid albums? I did not dream back then of drinking scotch whiskey all night and dying behind the wheel. My idea of glamour was drinking peppermint schnapps out of a paper bag. But now that I am older, I must agree with the great Bernard that he deserved a co-write on “Home At Last” for his critically important rhythm track.

42. “Midnite Cruiser”

My first favorite Steely Dan album was their debut, Can’t Buy A Thrill, probably because it comes closest to approximating a more conventional rock band from the early ’70s. Part of that impression comes from the singers in the band at that time, including David Palmer and drummer Jim Hodder, who takes the lead on “Midnite Cruiser.” A relatively straight-forward driving song, “Midnite Cruiser” spotlights how close early Steely Dan was to Bruce Springsteen’s earlier, jazzier, and jammier albums from the same period.

41. “Brooklyn (Owes The Charmer Under Me)”

David Palmer was out of Steely Dan by the second album, Countdown To Ecstasy, in spite of singing on the hit “Dirty Work” and his fine turn on this song. While Fagen was reluctant to take over as the lead singer, he proved to be the voice of the band. On “Brooklyn,” Palmer is smooth and professional, and while his performance is heartfelt, it doesn’t have that essential humanity that Fagen brings. The twisted, acerbic, nasally, conversational, and perfectly imperfect timbre that is uniquely Fagen’s own. Without that voice, Steely Dan truly would be aural wallpaper. But juxtaposing that one-of-a-kind voice with the spotless soundscapes of Steely Dan’s music creates an unusual resonance, a feeling that what we present to the world never aligns with who we really are. Fagen’s voice is the ghost in the machine.

40. “Everyone’s Gone To The Movies”

Another one of the great pervy Steely Dan songs, in this case about a man showing porno films to kids. “Soon you will be eighteen / I think you know what I mean / Don’t tell your mama / Your daddy or mama / They’ll never know where you been.”

39. “Pretzel Logic”

This is the title track from Steely Dan’s third album, which is the one where they started moving away from writing songs suited for playing live toward crafting albums with studio musicians and retreating into their own hermetic obsessions and world-building. The title literally means “twisted reasoning,” which is also a good explanation for the song “Pretzel Logic.” Ostensibly a lyric about time travel, “Pretzel Logic” also feels like an allegory for pining for the past, even the worst parts of it, which is a theme that Steely Dan will return to time and again.

38. “Haitian Divorce”

Steely Dan’s nostalgia for a time that you didn’t personally experience in a way makes them seem more like a Gen X or even millennial act; they don’t have that sense of self-satisfaction that is endemic to so much boomer-era rock. Another thing that explains Steely Dan’s surprising relevance for younger generations — and the obsessive nature of their converts — is their knack for writing about real things that sound made up, like “Haitian Divorce” from The Royal Scam. “You used to be able to go to Haiti and get a divorce real fast,” Becker explained. What’s left unclear is whether you can really drink something called a Zombie from the cocoa shell.

37. “West Of Hollywood”

While Fagen and Becker usually expressed ambivalence about their adopted home state of California, it remains one of their great subjects. For those who came to them later, listening to Steely Dan records would become a primary way to experience the changes that impacted California, and what it signified about the rest of the country, over the course of the ’70s. “It’s probably the funniest of the 50 states that I know of,” Becker said in 1977. Added Fagen: “We’re not as negative as The Eagles. They’re totally down on California.” Their writing about well-to-do and spiritually bereft California characters peaked with Gaucho — more on that later — but on Two Against Nature Fagen and Becker were able to pick up where they left off remarkably well with “West Of Hollywood,” a song about a torrid love affair set against the film industry that also introduces a new term for breast augmentation (“hooterie”) into the lexicon.

36. “Night By Night”

Side 1 of Pretzel Logic ranks among my favorite of all Steely Dan sides, as we’ll see as this list unfolds. “Night By Night” is one of the lesser-known tracks on Side 1, even though Fagen maintained that it was intended to be one of the album’s most commercial cuts. It’s most notable in Steely Dan history for essentially spiriting original drummer Jim Hodder out of the band; when he couldn’t give Fagen and Becker the buoyancy they wanted, they brought in a 19-year-old studio whiz kid named Jeff Porcaro, later of Toto, to nail the part. Truly a great moment in yacht rock history.

35. “Black Friday”

As Steely Dan became more successful and less concerned with touring, Fagen and Becker played less and less on their records, instead conducting their preferred studio musicians like a wide-lapeled and well-coked up orchestra. But occasionally they could still distinguish themselves instrumentally, like on the crooked businessman ode “Black Friday,” which features an outstanding guitar solo by Becker.

34. “Only A Fool Would Say That”

The most famous person associated with Steely Dan who is not Donald Fagen and Walter Becker, is probably Jeff “Skunk” Baxter, the walrus-mustachioed guitarist who played on the first three records before leaving to join the Doobie Brothers and then, later, for an unlikely but successful career as a military missile defense consultant. He was also a vocal Trump supporter, which gives him the sort of life arc that makes me believe he was actually invented by Fagen and Becker. The only reason I know that’s not true is that you can hear him speaking Spanish at the end of this track.

33. “Bad Sneakers”

Big fan of how Donald Fagen sings “Pina Colada my friend” in this song. Our nation’s top Pina Colada magnate, whoever that might be, should pay Donald Fagen $10 million to sing “Pina Colada my friend” in a blockbuster ad campaign, and then Fagen should write a song about the hilarity of commerce cheapening art.

32. “Fire In The Hole”

The first great Fagen vocal in my estimation. He’s called himself an aloof bystander in his own songs, but the passion in his voice on “Fire In The Hole” is anything but removed. While the imagery is war related, it feels like another outsider song, this time sympathizing with a “freak” trapped inside some stifling environment. You don’t have to psychoanalyze too deeply to understand how that could apply to two Duke Ellington fanatics stuck in the rock early ’70s rock scene.

31. “The Caves Of Altamira”

The song originated during Fagen and Becker’s joyless pop songwriter period in the late 1960s, when they tried and failed to conform to what their corporate bosses believed were hit songs. (Though they did manage to land one song on a Barbara Streisand album.) It’s hard to imagine Barbara or anyone else covering a song about a cave complex in Spain renowned for its bevy of ancient art. For the Steelies, it was another metaphor for getting lost in a bygone world in order to escape contemporary ennui, though what really drives home “The Caves Of Altamira” is that relentless Bernard Purdie groove.

30. “The Fez”

Why not stick with another song with a great Purdie backbeat? “‘The Fez’ is a disco song which suddenly has a lot of chords,” Becker once explained. To compensate for the extra chords, Steely Dan cut down dramatically on the words. This is a song about dancing (or doing “it”) wearing a goofy hat, end of story.

29. “Your Gold Teeth II”

The title references a song from Countdown To Ecstasy, but this is the rare sequel that’s superior. Prior to the recording of Katy Lied, Fagen and Becker procured a Bösendorfer piano for keyboardist Michael Omartian, after hearing and enjoying the instrument’s pure sounds on classical music records. (They wound up billing their label $13,000 for the purchase. The ’70s!) That clear, articulate piano sound is among the album’s sonic signatures, putting Omartian at the forefront of songs like “Your Gold Teeth II.” This song is also notable for the lyrical guitar solo by Denny Dias, who started in Steely Dan as a full-time member for the first three albums and then hung around as a session player on the next three.

28. “Doctor Wu”

Here’s an unfounded theory: Blood On The Tracks came out during the recording of Katy Lied, and I’ve always found Fagen’s vocals on the album to be somewhat Dylanesque. On “Doctor Wu” this underscores this song’s connection to “Tangled Up In Blue” with this line: “All night long / We would sing that stupid song / And every word we sang / I knew was true.”

27. “Barrytown”

Since we’re on the subject of wild classic-rock conspiracy theories, I wonder if Billy Joel heard this song and unconsciously ripped it off for his own “Allentown,” released eight years later. (There’s no question that Billy was imitating Steely Dan on his 1978 “art jazz” record 52nd Street, particularly the song “Zanzibar,” admittedly a pretty brilliant Countdown To Ecstasy era pastiche.) Of course, “Allentown” is a song about steel workers who get laid off during the Reagan administration, whereas “Barrytown” references the upstate New York stronghold of ’70s religious guru Sun Myung Moon.

26. “Pearl Of The Quarter”

Steely Dan songs are typically described as cynical, bitter, and even mean. But this deep-cut ballad from Countdown To Ecstasy is shockingly tender, saluting a New Orleans sex worker in a manner that can only be described as sentimental. Musically, “Pearl Of The Quarter” could almost pass for The Band, with pedal steel guitar weeping gorgeous over gently rollicking drums and barrelhouse piano. If this song had appeared on Gaucho, sweet Louise and her Cajun smile would have ended up on a low-rent movie set in the Valley shooting pornography. But as it is, “Pearl Of The Quarter” is a touching tribute that overflows with unbridled affection.

INTERMISSION

Uptown baby.

25. “My Rival”

Speaking of Gaucho, Steely Dan’s 1980 album is currently my favorite, and that seems to be an increasingly common opinion, particularly among the band’s younger generations of fans. At the time, Gaucho was viewed by many as a disappointment, its cold and despairing sound and even colder and more despairing lyrics alienating the masses who flocked to the lush and layered Aja. This was when Steely Dan pushed their reputation for being exacting perfectionists in the studio to the breaking point; read any profile of the band from this period and there will be at least one scene emphasizing how excruciatingly boring it was to make Gaucho. (“We both liked recording studios,” Becker explained. “As much as anything else, it was just coolest place to be on a hot afternoon.”) What I respond to in Gaucho is how that near-clinical approach to making records rhymes with Steely Dan’s themes at the time: dehumanization, spiritual death, cocaine. On “My Rival,” they connect these very ’70s concerns with the conventions of film noir in a manner that recalls Robert Altman’s The Long Goodbye: “I struck a match against the door / Of Anthony’s Bar and Grill / I was the whining stranger / A fool in love / With time to kill.”

24. “Don’t Take Me Alive”

“When I sing a song I just take the role of narrator,” Fagen told The Melody Maker in 1976. “It’s really quite impersonal, although the music in me, and the words themselves, can be very personal.” He then singled out this track from The Royal Scam that kicks off with some heavy guitar soloing from Larry Carlton. A paranoid narrative about urban violence in Los Angeles, “Don’t Take Me Alive” is a callback to the most rock-oriented style of their earlier records, which will be completely abandoned on the next two albums, Aja and The Royal Scam.

23. “Time Out Of Mind”

By Gaucho, Steely Dan was successful enough to add an actual rock-star guitarist to their menagerie. For “Time Out Of Mind,” they invited Mark Knopfler to lay down some licks after enjoying his playing on the first Dire Straits record. Fagen and Becker were apparently pleased with his efforts, though Knopfler was slightly traumatized by their famously persnickety methods, likening working with Steely Dan to “getting into a swimming pool with lead weights tied to your boots.” Nevertheless, the union of Knopfler and Steely Dan makes “Time Out Of Mind” a dad rock milestone.

22. “Bodhisattva”

Written by Fagen without input from Becker, this song is an early example of Fagen’s Far East fixations that would achieve full flower four years later with “Aja.” Otherwise, this is one of the great guitar-solo showcases in the band’s repertoire, with Denny Dias taking the first solo and “Skunk” Baxter taking the second. (I give Dias the slight edge.)

21. “Rose Darling”

Another Katy Lied song with a Dylanesque vocal from Fagen, particularly on the line “with lots of money in the bank / although I could be wrong.” This is also the first time that Michael McDonald’s backing vocals are prominent on a Steely Dan track, which requires me to reference this.

20. “Everything You Did”

If we think of the ’70s LA rock scene as a high school lunchroom, The Eagles were the jocks table, Fleetwood Mac were the beautiful rich kids table, and Steely Dan were the brilliant chain-smoking English-lit nerds table. But in true Breakfast Club fashion, the jocks and the nerds kind of got along. Steely Dan famously referenced The Eagles in the venomous “Everything You Did” as a pointed signifier in the mind of the song’s jealous narrator. “Turn up the Eagles the neighbors are listening,” he demands as they argue, because of course she’s into the era’s studliest, most confident band. The Eagles, much more famously, returned the favor with the “steely knives” reference in “Hotel California.” Hence the dynamic between these bands — The Dan mocks, and the Eagles laugh it off while laughing to the bank.

19. “Any World (That I’m Welcome To)”

“A lot of what you’d call bitter or cynical, we’d call funny,” Walter Becker once remarked to an interviewer. By that metric, Steely Dan’s albums only grew funnier as the ’70s progressed and the lyrics took on an increasingly bleaker tone. Though I have to admit that I can’t really laugh at “Any World (That I’m Welcome To),” a song about wanting desperately to leave your life by any means necessary. One of their saddest and most beautiful songs.

18. “Third World Man”

If “Any World” feels like a personal apocalypse, “Third World Man” is about an apocalypse apocalypse. “I saw the fireworks
I believed that I was dreaming / Till the neighbors came out screaming / He’s a third world man.” Incredibly, “Third World Man” came out of another track, “The Second Arrangement,” that was accidentally erased after several weeks and thousands of dollars spent trying to perfect it. Perhaps the sorrow over losing that song is what gives “Third World Man” its overwhelming feeling of desolation and foreboding. Though ultimately it feels appropriate for the final song on the final album of Steely Dan’s “classic” run.

17. “Rikki Don’t Lose That Number”

I love the Steely Dan original, but I can’t hear this song without thinking of John Mahoney’s iconic performance of the song in Say Anything, the truest representation of a middle-aged man driving and listening to Steely Dan in cinema history.

16. “Dirty Work”

And this is the truest representation of a middle-aged man driving and listening to Steely Dan in television history.

15. “Reelin’ In The Years”

Their most popular song, based on streams and classic-rock radio airplay. So of course Fagen and Becker have no use for it. “It’s dumb but effective,” Donald Fagen was the best compliment could muster up for it. Let me add to that: “Reelin’ In The Years” is Steely Dan’s Thin Lizzy song, one of their only flat-out rockers. Also, Elliott Randall’s blazing solo is supposedly Jimmy Page’s favorite by anybody, which is more than good enough for me.

14. “My Old School”

Another flat-out Steely Dan rocker about one the great flat-out rocker subjects, school and how much it sucks. A throwback to Fagen and Becker’s days at Bard College, where they bonded as two of the only non-rich kids at the school. (“It took me a long time to realize that, too,” Becker reminisced, “why everyone else had cigarettes and Porches.”) Whereas Alice Cooper fantasized about blowing up a school around this time in “School’s Out,” Fagen and Becker go one step farther in imagining a scenario that would get them to go back to their alma matter: “California tumbles into the sea / That’ll be the day I go back to Annandale.”

13. “Peg”

Most stories of ’70s rock excess involve musicians pissing away millions of dollars in the name of decadence and egotism. For Steely Dan, burning through barrels of money usually involved trying to achieve perfection and … pretty much achieving it. “Peg” is famous in the band’s lore for how Fagen and Becker tortured some of the finest session guitarists in Los Angeles in order to find the perfect solo. There were eight different players in all, including mainstay Larry Carlton and even Becker himself. That they landed on Jay Graydon has been described by the band’s producer Gary Katz as a “last ditch” effort, which is insane given how Graydon nails the right (and borderline impossible) mix of joyous abandon and deadly technical precision.

12. “Any Major Dude Will Tell You”

I have heard this song 1,000 times, I know every word by heart, and it is one of my very favorite Steely Dan tracks. I also have no clue what it’s about. I’ve read that when Fagen and Becker moved to California they thought it was funny that people called each other dude. The line about “a squonk’s tears” reminds of the Genesis song “Squonk,” but that came out two years later. Musically, “Any Major Dude” reminds me of the Wilco song “Jesus, Etc.,” and Wilco actually covered it right before recording Yankee Hotel Foxtrot. Is any of this significant? Yes? No? Maybe? Honestly, I have no clue. Great song, though.

11. “Josie”

Here’s an oft-made point that nevertheless is especially true for Steely Dan: Sometimes sounding “dated” can be the best possible attribute for a piece of music. Newcomers to Steely Dan inevitably hear them as a product of their time, a period when guys in their twenties (and also women, but mostly guys at this point) were allowed to spent bundles of money and time in order to make stupidly opulent albums for music fans to play on their stupidly opulent stereo systems. And those albums ended up evoking a unique era in American history, in which the social advances of the ’60s were depoliticized and reduced to vehicles for consumption and decadence. Put another away: Listening to Steely Dan to me feels like being smashed on champagne and coke while seated inside a luxury apartment in a Southern California high-rise the night that Reagan was elected. Or like lounging in a leather-lined booth in a sleazy-fancy singles bar in 1974. As much as I love the music, that time travel aspect of Steely Dan is a big part of the appeal for me. And as much as any song, the guitar lick and high-hat sounds at the start of “Josie” instantly put me in that headspace.

10. “Black Cow”

One of the all-time great Steely D grooves — take a bow, Paul Humphrey — though I wish Fagen and Becker hadn’t taken all the money from Lord Tariq and Peter Gunz.

9. “Show Biz Kids”

An oft-remarked upon aspect of this song is the meta reference to the “Steely Dan T-shirt,” which we’re told is outrageous. This confirms that Steely Dan exists in the Steely Dan universe, which means that other characters in Steely Dan songs also are aware of Steely Dan. Weirdly, the rich and trendy LA kids described in this song seem like the least likely Steely Dan fans in any Steely Dan song. I can see the guy in “Third World Man” having a copy of Aja. But the people in “Show Biz Kids” probably would’ve been more into Bowie or Zeppelin than The Dan in 1973. In spite of this minor inconsistency, this song is a masterpiece.

8. “Do It Again”

I can’t believe I’ve gone this deep into the list without commenting on the awfulness of the Can’t Buy A Thrill album cover. Fagen and Becker themselves made fun of the cover in the liner notes of The Royal Scam CD reissue, though they suggested that The Royal Scam cover might actually be worse. (It’s not.) The iconography — the prostitutes, the big red lips, the sporty font — is like C-grade Warhol and really has nothing to do with the band. Of course, the first song on the album, “Do It Again,” also seems like an anomaly. A Latin-tinged rocker with a smoking electric sitar solo by Denny Dias, “Do It Again” was perfect fodder for FM radio in 1972, which explains why Steely Dan never made another song remotely like it. For years as a kid, I thought it was a Santana track; if it were a Santana song, it would also be my eighth favorite Santana song.

7. “Aja”

So many Steely Dan songs are about longing, but this one is the most evocative. It can be read as a love song, but the melancholy feel of the music makes me think that it’s really about what one would imagine being in love to be like. “Aja” is also the pinnacle of Fagen and Becker completely eschewing the idea of a band as a fixed group of musicians, and instead just hiring the most incredible players they could find. In this case, that means saxophonist Wayne Shorter, whose solo is the single grandest moment on any Steely Dan record; and drummer Steve Gadd, whose own solo might be the second grandest.

6. “Babylon Sisters”

I came very close to simply listing the first four songs from Gaucho at the top of this list. The whole album is incredible, but those four opening tracks are probably Fagen and Becker’s peak as songwriters and social commentators. This might be a slight exaggeration, but I think they wrote about Los Angeles in the ’70s on Gaucho as well as Joan Didion did about LA in the ’60s in her book The White Album. Just as Didion was obsessed with writing about paradise lost, “Babylon Sisters” evokes a sun-drenched utopia that has been allowed to crumble from within. Though the song itself was painstakingly assembled to have zero flaws; a famous Rolling Stone profile written by Robert Palmer describes Fagen and Katz poring over the 50-second fade at song’s end for four hours. (“This is the happiest night of my life,” Fagen says sardonically once they get it right.)

5. “Kid Charlemagne”

Alas, I couldn’t follow through with my Gaucho plan without leaving “Kid Charlemagne” out of the top five, which would just be wrong. This was among the first Steely Dan songs that really turned me on to them. In the early aughts, my burgeoning Steely Dan fandom was fed by Pharrell Williams, who I loved because of N.E.R.D. and his work with The Neptunes. Pharrell is one of Steely Dan’s most famous fans, and I imagine he also loves “Kid Charlemagne” (as did Kanye West of course) because it represents Bernard Purdie and especially Larry Carlton at the height of their powers. For real though: Is there gas in the car? Is there gas in the caaaar?

4. “Glamour Profession”

A novel in the form of a seven-minute song. Fagen and Becker claimed they wrote the hook in college, but they could only write the lyrics after they become hugely wealthy and had an inside view of a world that fascinated and repelled them. The storytelling in “Glamour Profession” is incredibly clear: A drug dealer has an appointment with a star athlete, Hoops McCann. The star has arranged for huge quantities of cocaine to be smuggled in from Colombia so he can throw lavish parties. The hold of addiction is felt in the brittle rhythm section and the spine-tingling ice-pick guitar licks played brilliantly by Becker. “Living hard will take its toll” is the song’s nutgraf, a truism experienced personally by Becker as drugs consumed his own life at the time.

3. “Deacon Blues”

Steely Dan’s conflicting themes — nostalgic longing and skepticism that anything was ever actually good — come together beautifully in “Deacon Blues.” The lyric is a first-person narrative about a man who fantasizes about being a romantic artist that dies young. (The tragicomic opening line is my favorite in any Steely Dan song: “This is the day of the expanding man.”) Nobody writes about being washed better than Fagen and Becker, who were only in their mid-20s when they wrote and recorded “Deacon Blues.” These guys were born washed, which as a person who was also born washed makes me love them even more. You could say they are making fun of the guy in this song, I guess. But my favorite Steely Dan songs tend to be really sad even when they are really funny. Yes, it’s funny that this character would want to die in a car accident. But it’s also sad that he wants to be important and never will be. It’s funny because it’s true, and it’s not funny because it’s true.

2. “Hey Nineteen”

Their funniest song and their perviest, as if these things are ever mutually exclusive with Steely Dan. Becker’s favorite writer was Vladimir Nabokov, who also had a talent for writing tragic comedies and comic tragedies. But it’s possible at this point that “Hey Nineteen” has usurped even Lolita as the go-to signifier for older men pursuing younger women in order to feel like they’re not dying a little bit every single day. The key to “Hey Nineteen” is how Steely Dan is able to fully convey how pathetic the protagonist is while also showing us how he seems himself in his own mind, as a cool seducer brandishing tequila and coke. Nobody wants to be that guy, but it sure is enjoyable to spend five minutes and seven seconds with him.

1. “Gaucho”

A perfect song I can’t imagine anyone else writing. (Well, I can imagine someone else writing the music — the melody is lifted from “Long As You Know You’re Living Yours” by Keith Jarrett, who sued and was given co-writing credit.) There are many funny lines and phrases in “Gaucho” that have since become in-jokes for fans: bodacious cowboys, The Custerdome, the spangled leather poncho. But this for me is one of the saddest songs of all time. A rich man brings a hustler back home to his lover, and the couple argues about what to do with this poor kid. Finally, the rich guy agrees to take the kid out by the freeway and dump him off there. “Doesn’t he have a home?” someone asks, but it’s more of an afterthought than a real concern. After so many sympathetic songs about outsiders, “Gaucho” has a real downer ’70s ending — people are there to be used and then thrown away. That is the nature of life in the modern world. In the end, what can you do but laugh?

Steely Dan is a Warner Music artist. Uproxx is an independent subsidiary of Warner Music Group.

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