As their first album is 50 years old in November, we choose the band’s most distinctive works, which include stories about capitalism, drug traffickers, and midlife crises.

20. Any Major Dude Will Tell You (1974)

Steely Dan’s trademark style of caustic pessimism is seldom described as charming, but the acoustic guitar-driven tune Any Major Dude Will Tell You, in which a despondent acquaintance is ostensibly unironically exhorted to see the bright side, fits the bill.

19. Black Friday (1975)

The Steely Dan song that appears most relevant in 2022 is probably “Do Just What I Please,” which describes how a financial collapse so terrible that businesses commit themselves makes them want to flee into the woods. The protagonist is implied to be a catastrophe capitalist rather than a typical rat race escapee in a classic Dan twist.

18. Show Biz Kids (1973)

Show Biz Kids has a (relative) looseness and roughness that would be eliminated from following Steely Dan albums. Rick Derringer plays stinging slide guitar, while the lyrics take a stinging jab at the arrogant, drugged-out titular characters who “don’t give a fuck about anybody else.” Although it is understandable, it is nevertheless interesting to hear.

17. Doctor Wu (1975)

The lyrics of Doctor Wu are a prime example of Steely Dan’s short story-in-song technique: a drug addict learns that the girlfriend who has been supporting him has also developed a habit. However, Phil Woods’ saxophone is the true star of the song: initially smooth, it transforms into frenzied free blowing as the narrative reaches its climax.

16. Gaucho (1980)

Disaster beset Steely Dan’s last record in 20 years, including an overdose death of their personal manager who was also Walter Becker’s fiancée, as well as addiction, vehicle accidents, studio mishaps, and addiction. Keith Jarrett successfully sued over the title track, which doesn’t lessen the splendor of its story of social shame.

15. Pretzel Logic (1974)

Essentially Steely Dan’s interpretation of blues-rock It moves along in a traditional manner, repeating the first couplets of each stanza, although the chords and harmonies aren’t very bluesy. A typical Dan insult appears in Pretzel Logic’s title tune, which may be about time travel: “You must be joking son / Where did you get those shoes?”

14. Cousin Dupree (2000)

Cousin Dupree, a song from Steely Dan’s return album Two Against Nature, is a distant cousin of Gaucho’s Hey Nineteen and invites the audience to chuckle at a deadbeat sleazeball trying to woo a much younger lady. The plot of the film You Me and Dupree, according to Becker and Donald Fagen, was lifted from the song.

Steely Dan in the early days: (from left) Denny Dias, Walter Becker, Donald Fagen, Jeff Baxter and Jimmy Hodder.

Steely Dan in the early days: (from left) Denny Dias, Walter Becker, Donald Fagen, Jeff Baxter and Jimmy Hodder. Photograph: Charlie Gillett Collection/Redferns

13. Aja (1977)

Deciphering Aja’s cryptic lyrics to determine their meaning—do they refer to heroin addiction?—has become something of a cottage business on the internet. An obsessional relationship? An obsession with bebop? Perhaps it’s best to just enjoy the music, which stretches out for eight wonderful minutes with help from jazz greats Steve Gadd and Wayne Shorter.

12. Your Gold Teeth II (1975)

Although Your Gold Teeth from Countdown to Ecstasy is excellent, its nominal successor is even better: a jazz-rock hybrid with genuine swing, featuring some incredibly nimble drumming by Jeff Porcaro, deftly navigating the time signature shifts, liquid guitar courtesy of Denny Dias, and a chorus stuffed with gorgeous harmonies.

11. Rikki Don’t Lose That Number (1974)

Rikki Don’t Lose That Number, the biggest hit of Steely Dan’s career and, one assumes, the only US Top 5 single to feature someone playing the percussion instrument the flapamba, appropriates a Horace Silver riff and turns it into fabulously idiosyncratic pop gold. It is the ideal illustration of Pretzel Logic’s wilfully concise approach.

10. Babylon Sisters (1980)

Gaucho is largely stripped down by Steely Dan standards, but Babylon Sisters returned to their traditional style of complex chord sequences with spectacular, if painfully world-weary, results. This was aided by the “Purdie shuffle” beat, which is a trademark of legendary drummer Bernard “Pretty” Purdie.

9. Reelin’ in the Years (1972)

A successful song that Fagen and Becker notoriously dissed as “dumb but effective” and “no fun” in later years. Contrary to popular belief, it is excellent and has had a significant impact. The songs The Boys Are Back in Town by Thin Lizzy and So It Goes by Nick Lowe both include elements of this song.

Walter Becker and Donald Fagen in Los Angeles, California, in the 1970s.

Walter Becker and Donald Fagen in Los Angeles, California, in the 1970s. Photograph: Chris Walter/WireImage

8. My Old School (1973)

The outstanding tune on Countdown to Ecstasy was inspired by a memory of a drug raid at Bard, the elite liberal arts college where Fagen and Becker first met. The gritty rhythm of the song’s R&B-influenced beat mirrored the bitter tone of the experience. Fagen returned to get an honorary degree despite promising never to do so in the future.

7. Black Cow (1977)

He’s tired of being a shoulder to weep on when the wayward girl eventually stumbles home “like a gangster on the run,” according to the frontline report from the friend-zone that opens Aja, which was subsequently sampled by MF Doom and Beyoncé.

6. Bad Sneakers (1975)

A transplanted New Yorker who fears the West Coast may drive him insane views the extravagance of mid-’70s LA through his eyes. The song’s melody is instantly recognizable, the lyrics clearly hint to autobiography, and the curiously frenzied piano comping during the guitar solo breaks up the smoothness.

5. Don’t Take Me Alive (1975)

Even by Steely Dan standards, Don’t Take Me Alive’s lyrics—about a criminal locked up with “a case of dynamite” who has a kind of dark spiritual epiphany—are powerful; the music, particularly Larry Carlton’s exquisitely flowing guitar—is wonderful.

4. Do It Again (1972)

The first track of their debut album’s rhythm suited the 1970s trend for Latin rock, but that was the last time they had anything in common with Santana. It’s a great tune as well as a tone-setting calling card with its sarcastic, detached lyrics about human frailties and killer solos—electric sitar and cheap organ, no less—that set the bar high.

3. Deacon Blues (1977)

Despite Fagen’s claims that Deacon Blues is about “losers,” the song’s lyrics, which describe the dashed hopes of a midlife crisis but primarily speak to the liberating power of music, have a warmth to them. The brass arrangement is delightful, the sax solo is roaring, and the intro is a masterpiece in and of itself.

2. Kid Charlemagne (1976)

The greatest guitar solo in Steely Dan’s discography, Kid Charlemagne features 30 seconds of exhilarating twists and turns, its joyousness intriguingly at odds with the song’s overall tone. The song is a loose but compelling retelling of the story of Owsley Stanley, an acid dealer to Ken Kesey’s Merry Pranksters.

1. Peg (1977)

Fagen refuted one theory that the song was about tragic 1920s actor Peg Entwistle, but it is undisputed that Peg is a masterpiece. It is filled with infectious hooks, some of which famously powered De La Soul’s 1989 hit Eye Know. Its disco-infected breeziness also conceals a wealth of musical complexity (Fagen’s online breakdown of the song’s chords is a 12-minute riot of plagal cadences. It succeeds in being both the Steely Dan song that those who claim to detest Steely Dan like and the pinnacle of Steely Dan.

Thanks to at The Guardian whose reporting provided the original basis for this story. 


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