Steely Dan’s 20 greatest songs – ranked!

With November marking 50 years since their debut album, we pick the best of the band’s idiosyncratic output, with tales of capitalism, drug dealers and mid-life crises

20. Any Major Dude Will Tell You (1974)

Charming is seldom an adjective applied to Steely Dan’s patent brand of sardonic pessimism, but it fits the relatively simplistic, acoustic guitar-driven Any Major Dude Will Tell You, on which a depressed friend is apparently unironically encouraged to see the bright side: it’s a genuinely sweet song.

19. Black Friday (1975)

Perhaps the Steely Dan that seems most apropos in 2022: financial collapse so severe that businessmen kill themselves leads to a desire to escape into the wilderness to “do just what I please”. In a classic Dan twist, there’s an implication that the protagonist isn’t an ordinary escaper from the rat race, but a disaster capitalist.

18. Show Biz Kids (1973)

Stinging slide guitar by Rick Derringer, stinging lyrical assault on the entitled, drugged-out titular characters who “don’t give a fuck about anybody else”: there’s a (relative) looseness and roughness to Show Biz Kids that would be expunged from later Steely Dan albums. You can understand why, but it’s still intriguing to hear.

17. Doctor Wu (1975)

The lyrics are a perfect example of Steely Dan’s short-story-in-song approach – drug addict discovers the girlfriend who has been helping him has also succumbed to a habit – but the real star of Doctor Wu is Phil Woods’ saxophone: initially smooth, it breaks into frenzied free blowing when the story reaches its denouement.

16. Gaucho (1980)

Steely Dan’s last album for 20 years was plagued by disaster – addiction, car accidents, studio mishaps, the overdose death of their personal manager, who was also Walter Becker’s girlfriend. There was also a lawsuit: Keith Jarrett successfully sued over the title track, which doesn’t make its saga of social embarrassment any less splendid.

15. Pretzel Logic (1974)

Effectively Steely Dan’s take on blues-rock – it shuffles along in time-honoured style, the opening couplets of each verse repeat, but there are some very un-bluesy chords and harmonies – Pretzel Logic’s title track may be about time travel, and features a classic Dan put-down: “You must be joking son / Where did you get those shoes?”

14. Cousin Dupree (2000)

The pick from Steely Dan’s comeback album Two Against Nature, Cousin Dupree is itself a distant relative of Gaucho’s Hey Nineteen: the listener is invited to snigger at a deadbeat sleazeball attempting to pick up a much younger woman. Becker and Donald Fagen later claimed the premise of movie You Me and Dupree was stolen from the song.

13. Aja (1977)

There’s something of an online cottage industry in trying to work out what Aja’s oblique lyrics are about: heroin addiction? An obsessive love affair? A passion for bebop? Maybe it’s better to just luxuriate in the music, which sprawls for eight marvellous minutes, assisted by jazz legends Steve Gadd and Wayne Shorter.

12. Your Gold Teeth II (1975)

Your Gold Teeth from Countdown to Ecstasy is great, but its nominal successor is even better: a jazz-rock hybrid that genuinely swings, complete with some extraordinarily nimble drumming by Jeff Porcaro, deftly navigating the time signature shifts, liquid guitar courtesy of Denny Dias and a chorus stacked with wonderful harmonies.

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

The biggest hit of Steely Dan’s career – and, one assumes, the only US Top 5 single to feature someone playing the percussive instrument the flapamba – Rikki Don’t Lose That Number steals a riff from Horace Silver and transforms it into fabulously idiosyncratic pop gold: the perfect example of Pretzel Logic’s wilfully concise approach.

10. Babylon Sisters (1980)

A lot of seventh album Gaucho is stripped back by Steely Dan standards, but Babylon Sisters reverted to their traditional style of complex chord sequences with spectacular if painfully world-weary results, underpinned by legendary drummer Bernard “Pretty” Purdie’s signature “Purdie shuffle” beat.

9. Reelin’ in the Years (1972)

A hit single famously dismissed by Fagen and Becker in subsequent years as “dumb but effective” and “no fun”. One must beg to differ: it’s terrific, and proved hugely influential: you can hear it in the DNA of both Thin Lizzy’s The Boys Are Back in Town and Nick Lowe’s So It Goes.

8. My Old School (1973)

A memory of a drugs bust at Bard, the private liberal arts college where Fagen and Becker met, was transformed into the standout track from Countdown to Ecstasy, its bitter tone reflected by the toughness of its R&B-inspired groove. Contrary to his avowal never to return, Fagen did go back to get an honorary doctorate.

7. Black Cow (1977)

The mood-setting opener of Aja: a super-supple funk groove – later sampled by MF Doom and Beyoncé – over which a frontline dispatch from the friend-zone unfurls: he’s sick of providing a shoulder to cry on when the errant lady finally staggers home “like a gangster on the run”.

6. Bad Sneakers (1975)

The decadence of mid-70s LA seen through the eyes of a displaced New Yorker who’s certain that the west coast is sending him round the bend. There’s a distinct hint of autobiography in Fagen’s lyrics, the melody is hit-single catchy and the oddly frantic piano comping during the guitar solo disrupts the smoothness.

5. Don’t Take Me Alive (1975)

“A man of my mind can do anything”: even by Steely Dan standards, the lyrics of Don’t Take Me Alive – in which a criminal holed-up with “a case of dynamite” experiences a kind of dark spiritual revelation – are striking; the music – not least Larry Carlton’s beautifully fluid guitar – sublime.

4. Do It Again (1972)

The rhythm of their debut album’s opening track fitted with the 70s vogue for Latin rock, but therein ends the similarity with Santana. With its acerbic, dispassionate lyrics about human frailties and killer solos – electric sitar and cheap organ, no less – it’s a tone-setting calling card, as well as a classic song.

3. Deacon Blues (1977)

For all Fagen’s assertions that Deacon Blues is about “losers”, there’s a warmth about his lyrics, which detail the thwarted dreams of a midlife crisis but essentially concern the liberating effect of music: the brass arrangement is blissful, the sax solo roars and the intro is a masterpiece in its own right.

2. Kid Charlemagne (1976)

A loose but gripping retelling of the saga of Owsley Stanley – acid dealer to Ken Kesey’s Merry Pranksters – alternately impressed by its subject and witheringly scornful, Kid Charlemagne also features the greatest guitar solo in Steely Dan’s catalogue: 30 seconds of thrilling twists and turns, its joyousness intriguingly at odds with the song’s overall tone.

1. Peg (1977)

Peg’s subject matter caused endless speculation – Fagen denied one theory, that it was about doomed 1920s actor Peg Entwistle – but what is beyond doubt is the sheer quality of the song itself: laden with infectious hooks – several of which famously powered De La Soul’s 1989 hit Eye Know – its disco-inflected breeziness is deceptive, hiding umpteen layers of musical complexity (Fagen’s online explanation of how its chords work is a 12-minute riot of plagal cadences and tritone substitutes) and perfectionism: the guitar solo legendarily took seven attempts by top session players. Peg manages to be both the Steely Dan song people who profess to hate Steely Dan like, and Steely Dan’s apotheosis.


Alexis Petridis

The GuardianTramp

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