Steely Dan has been described as antiheroes of the music industry, best known for their ironic lyrics and masterful blend of several genres into what can only be described as a Steely Dan sound.
Despite disbanding at the end of the 70s, they’ve always had a cult following, which was rewarded when the duo reunited in 1993. Ranked as one of the greatest duos of all time by Rolling Stone and selling over 40 million albums worldwide, Steely Dan is truly one of the greats. In this article, we’ll go over 25 of their best songs of all time.
1. Reelin’ In The Years
Reelin’ In The Years was released as the second single from Steely Dan’s 1972 Can’t Buy a Thrill album and saw immediate success. It peaked at number 11 on the US Billboard Hot 100 and featured an excellent guitar solo that would eventually be ranked as the 40th-best guitar solo of all time by Guitar World.
It’s basically the essence of Steely Dan in song, a prime example of a careless goodbye to an ex set to a bouncing groovy rhythm.
2. Do It Again
Do It Again might be the most quintessentially-Steely Dan song of all time. It featured solos from an electric sitar and organ while sardonically invoking the weakness of humanity and sounding like a Carlos Santana song in the intro. It’s a classic song for Steely Dan and the music world as a whole, easily ranking as one of their best and signature songs.
3. My Old School
You might believe that the song refers to the glory days and nostalgia of student life, and this one… does. The lyrics refer to a drug bust at Bard College while Fagen and Becker were students, mentioning that a female student betrayed them to the local prosecutor.
After being arrested and having his hair cut off in jail, it’s no wonder why Fagen refuses to go back until California falls into the sea. The song was a fun one and a bit of a curveball, even from them, that still charted and made it to number 63 on the Billboard Hot 100.
Fagen describes this treat of a jazz-rock song as being about “tranquility that can come of a quiet relationship with a beautiful woman” It ended up being the longest song the band would record before disbanding in 1981, featuring both a drum and saxophone solo with references packed throughout the entire eight-minute song.
Another track from their Aja album, Peg, tied Rikki Don’t Lose That Number and Hey Nineteen for Steely Dan’s longest-charting single at 19 weeks. Its sarcastic lyrics, chill piano play, and overall light pop feel helped set it apart and sent it rocketing up to number 11 on the Billboard charts in 1978.
6. Don’t Take Me Alive
You’d typically rather not die when faced with an overwhelming enemy, but Steely Dan took this song the other route. There are no hidden metaphors or references here, Don’t Take Me Alive paints the story of a violent criminal holed up with a load of dynamite, ready for suicide-by-cop.
The dynamite, though, seems to take out the cop, who is implied to be the character’s father, taking the song on a dark twist that’s essential to Steely Dan.
7. Babylon Sisters
Babylon Sisters served as Steely Dan’s last rock track before their triumphant return with the Two Against Nature album in 2000. Babylon as a fallen city is used as a nod to the self-destructive tendencies that follow indulgent behavior, with Babylon Sisters referring to fallen women and shallow experiences with them.
8. Black Cow
The first track on their Aja album, Black Cow, is about a man talking about his girlfriend’s behavior, making him question the relationship and her character as a whole. The big black cow in the song refers to a root beer float, though whether or not it’s an alcoholic one with bourbon and Kahlua, we can’t say for sure…. But probably.
9. Rikki Don’t Lose That Number
Rikki Don’t Lose That Number would become Steely Dan’s most successful song in terms of chart performance, making it to number four on the Billboard Hot 100 in 1974. The Rikki in the song was a woman that Fagen had a crush on in college, with the song describing the romance that never was.
While incredibly popular, the song had numerous rumors running rampant about it, saying that it was trying to give secrets on safely transporting dope around, but the band shot those down fast. In the end, it’s softer, less abrasive, and fairly straightforward for a Steely Dan song, but that’s also probably why it was so commercially successful.
10. Black Friday
The gold crash of 1869 is one of the market crashes that gave us the Black Friday holiday in the US, where investors tried driving up the price of gold only for the government to release gold into the market and destroy their investment. Steely Dan used the event as inspiration for the song Black Friday before the holiday was named, portraying a financial meltdown as an excuse for apocalyptic partying.
11. Bad Sneakers
Bad Sneakers had such a catchy melody that the band’s producer regretted releasing it as the second song from the Katy Lied album instead of making it the first. It really can be viewed as Fagen’s thoughts on spending time on the West Coast after leaving New York and his overall disdain for the lifestyle. This was the first song Michael McDonald did vocal work for the group, but not his last, regularly performing as a background vocalist for Steely Dan until 1980.
12. Deacon Blues
Deacon Blues was another one of Steely dan’s best-performing songs on the charts, reaching number 19 on the Billboard charts in 1978 and number 17 on the Cash Box Top 100. Rolling Stone even listed the song at number 214 on their 2021 list of the Top 500 Greatest Songs of All Time. Deacon Blues stood as Steely Dan’s fifth Top 20 hit, remaining within the Top 40 for eight weeks.
13. Your Gold Teeth II
Your Gold Teeth II is a wonderfully complex and surprisingly upbeat song from a usually dark group, full of cynicism and sarcasm. It mirrored the duo’s views on music, where if you think someone is a good bet, go ahead and take it.
14. Doctor Wu
You can bet that the weirder a Steely Dan song is, the more likely it is based on some real person or event, and FYI, Dr. Wu is a real person.
Gaucho is one of the more obvious songs on its namesake album, serving as a love song from Fagen to Becker and discussing Becker’s heroin addiction and how much of a toll it’s taking on their work.
16. Show Biz Kids
Show Biz Kids was the first single to be released from Steely Dan’s 1973 album Countdown to Ecstasy. It’s got an infectious rhythm, driven by a tinkling type of percussion that helped launch the song up to number 61 on the Billboard Hot 100.
17. Kid Charlemagne
Steely Dan fused funk rhythms with jazz harmonies and rock instruments to create Kid Charlemagne, which even includes one of the greatest guitar solos of all time according to Rolling Stone.
The song tells the story of a drug dealer on the west coast in the 60s, loosely based around LSD chemist Owsley Stanley. The song was another highlight of their The Royal Scam album in 1976 and made it to number 82 on the Hot 100 that year.
18. Hey Nineteen
Hey Nineteen was probably the best song from Gaucho if you look at it from a commercial perspective. The interpretations can vary, from a middle-aged man being disappointed in a young lover not getting his older references to him sitting alone and doing some drugs.
The song peaked at number 19 on the US Billboard Hot 100 in 1981, staying on the chart for 19 weeks (ironic, ain’t it) and tying for Steely Dan’s longest run on the charts for a single.
19. Cousin Dupree
When an artist comes back after years away, you’d usually expect some kind of growth. With Steely Dan, you got some, but their minds were still solidly placed in the gutter. Cousin Dupree was the tale of the futile attempts of a dude to seduce his younger cousin, talking about how she’s grown so much since they were young and asking for a kiss for old times’ sake.
In 2006, when Owen Wilson’s movie, You, Me, and Dupree came out, Steely Dan posted a letter on their website saying the title was derived from this song, ending in a funny exchange between the group and Wilson who said he had no idea who they were and was focusing on his next movie, Hey 19, which was another of the band’s songs.
20. Pretzel Logic
Have you ever considered the bridge of a song to be a time machine? That’s pretty much what you get with Steely Dan’s Pretzel Logic. This bluesy song references Napoleon, minstrel shows, and all manner of cooky historical things. Overall, the song received a lot of praise from publications like Billboard and Cashbox, reaching number 57 on the Billboard charts in 1974 and serving as one of the singles released from its namesake album.
21. Any Major Dude Will Tell You
Also coming in hot from the Pretzel Logic album, Any Major Dude Will Tell You would later be released as the B-side to Rikki Don’t Lose That Number and on several of the band’s compilation albums. If you don’t know what a squonk is, don’t worry; neither did the musicians who worked on the song with Fagen and Becker. The song was widely acclaimed as one of Steely Dan’s smoothest works, simultaneously creating something utterly weird and lovely.
Bodhisattva refers to a human who has reached perfect enlightenment, much like the Buddha, and can leave the physical world but chooses to remain to help others find the same state.
Of course, that gets a bit twisted when Steely Dan is involved, with their version of a Bodhisattva finding enlightenment through righteous guitar solos, of which the song has two. The song was essentially a parody of the way westerners look at eastern religions, oversimplifying the broad spectrum and curious details of it, ultimately perverting it.
23. Dirty Work
Dirty Work first appeared on Steely Dan’s debut album, Can’t Buy A Thrill, in 1972. It describes an affair between a married woman and a man who is certainly not her husband, reveling in the wrongness of it like a soap opera.
While the man knows he’s being used, he likes her too much to leave. You might have also heard the song elsewhere, as it was used on the season three premiere of The Sopranos, played while the FBI watched Tony Soprano driving around town.
24. Fire in the Hole
Steely Dan is notoriously hard to “get,” with people claiming to know exactly what all of their songs mean and generally getting it wrong. I searched for the meaning behind Fire In The Hole and didn’t find much.
It’s an excellent song that sits up with the duo’s best, so in Steely Dan’s spirit, I’ll give you the funniest interpretation of it I found. It’s basically just about a dude that has to pass gas, but he’s in a public place and can’t get away. Frankly, there are a few solid references that could be related to farts, and I wouldn’t put it past Steely Dan to put a gas-laden gem on their debut album.
25. The Fez
No, not Fez from That 70’s Show (that came from F-E-S, standing for Foreign Exchange Student). The Fez is the only Steely Dan song in history to give a writing credit to a third writer, which is attributed to Paul Griffin who also played the organ for the song.
He came up with a few bars that were missing, so they felt they should throw him a writer credit for it. For the meaning of the song, it’s a fairly safe bet to say “the fez” refers to a condom, and that makes this a safe-sex song well before those truly came about, another example of Steely Dan being ahead of their time. If you do want to delve into the meaning of phrases in their work, though, the Steely Dan Dictionary is a decent place to go.
As a contributing writer for Music Grotto, Dakotah writes and produces professional music/media content. He works closely with editorial staff to meet editorial standards and create
quality content for the Music Grotto website. Dakotah is passionate about music in a wide variety of genres, from hip-hop to country and lo-fi to metal, and he enjoys creating music pieces for Music Grotto.