I’m starting a new semi-regular post on the blog. I call it the 12 Song Challenge. The goal of this is simple – to share some music I love, and to do so in a format that allows for you to listen to the songs. I’m building playlists on Spotify and embedding them in the posts, and then giving my explanations for why I chose these 12 songs from this artist. In most cases these will be my personal “Best Of” lists for certain artists or eras.

First up is Steely Dan — and more specifically, the original 1972-81 itineration of Steely Dan. I’ve actually got all the songs from that era ranked in order, but I’m only going to give you my top 12. Here’s the playlist, with my 12th-ranked song first and my top song last. Below the playlist you can find my explanations for each choice.

(12) Deacon Blues: Maybe the most meticulous loser’s anthem in rock history. I never get tired of this one, despite its length and verbosity. The lyrics are fascinating and deep, and the musical touches are exemplary. This is NOT a song that is going to get most people under the age of 30 excited, but it’s an excellent reflective piece for older adults…or for people with older minds.

(11) Hey Nineteen: I read a blog post once that described this song as being about “growing old disgracefully”…and that’s true! But it’s more than that. Yeah, it’s a sleazeball anthem, but it’s also a sobering realization of aging, lost coolness, and the alienation of time. It’s also interesting to compare the guitar solo in the coda with the one in Haitian Divorce (#9 below). Whereas Haitian Divorce’s outro solo just oozes sadness, this one is blissfully confused. Probably due to the fine Colombian.

(10) Haitian Divorce: This one tends to get criminally overlooked, and I think that’s largely because The Royal Scam is their most difficult album to get into. Most SD lyrics are clever. These lyrics are clever AND cinematic in execution. The talk box guitar solos are similarly excellent — not just good solos, but great, evocative musical additions that build up the song’s narrative without any words being spoken. The tone that the guitar achieves in the coda is one of the most human-sounding emotional shifts you’ll ever hear in a guitar.

(9) Midnight Cruiser: This song is the best un-Steely Dan song that they ever recorded. There were a few songs like this on the debut album (Change of the Guard is the other primary example) but this is by far the best. It manages to do what songs like Dallas and Sail The Waterway couldn’t, and that’s achieve a perception of lyrical depth and backstory without really saying much. The music is also delightful, but in a very traditional rock approach. Dias and Baxter do a fine job of mixing tone with pacing, and avoid the sort of note overload in a couple of the other (more famous) songs on the album.

(8) The Caves of Altamira: One of their REALLY old songs, this pops up on the Sun Mountain “rarities” album and in a few other places. The metamorphosis that it undergoes between the piano-only demo version and the full-blown Royal Scam version is quite impressive, and this stands as a great example of what SD could do with a brass section living within the confines of a well-constructed song. The lyric is also charming and touching, adult yet childlike at the same time.

(7) King of the World: More cinematic lyrical execution, and this time we enter the science fiction realm. I can’t listen to this song without thinking of the old PC games “Wasteland” and “Fallout”, and apparently the genesis of the subject matter for the song was the cult film “Panic In The Year Zero”. The slow-erupting guitar solo in the coda of the song is one of the great hidden pleasures of the SD canon.

(6) Peg: This song engenders a lot of hate from certain corners, and I can understand why. It’s probably the slickest thing that SD ever did, it’s got a maddeningly bouncy hook that lodges itself in your brain, and it has the sort of holier-than-thou English major attitude that so many find infuriating. But it’s also got a stunning variety of items going on underneath the surface, from the slap-happy bassline to the freak-show Michael McDonald backing vox. The lyrics are hilarious as well, once you figure out what they’re about.

(5) Babylon Sisters: The line in ‘Deacon Blues’ is “Languid and bittersweet”, and that precisely describes this song. Similar lyrical themes to Hey Nineteen, but on the other side of the divide.

(4) Black Cow: Another song where hearing the demo version actually enhances your enjoyment of the officially released version. The demo (from the Katy Lied sessions, I believe) is just Fagen and his piano, leaving both the lyrics and the atmosphere to linger like a cigarette under blacklight. The Aja version has so many amazing little add-ins throughout – the way the electric piano interfaces with the bass, the brass section weaving its way in and out of the transitions between chorus and verse, the “So Outrageous!” drop-ins from the background vocalists. For a band known (and often criticized) for its surgical precision in the studio, this may be the most precise song they ever did that still retained the free soul of the jazz artists they emulated.

(3) Doctor Wu: A lot of people call this song their favorite, and it’s got a great amount of things going for it. An awesome three-way storyline (with one of the partners obviously being heroin), that orgasmic saxophone solo, the almost Caribbean vibe, and a structure that managed to achieve both climax and catharsis twice within the same song. This was my favorite SD song for the longest time, but probably suffers now a bit due to overexposure at a younger age.

(2) Any Major Dude Will Tell You: Such a relaxed and friendly song, free of the poison pen that rules so many SD songs. Even the guitar solo is inviting and warm. One of those songs that is almost impossible to not enjoy.

(1) Pretzel Logic: My favorite time-travel song of all time. A compact song with a marvelous vamping chord sequence, a chorus that starts and ends on the same chord but somehow makes it sound completely different, and lyrics that bridge the gap between surrealism and intellectualism. Becker also contributes his best-ever solo on this song, which is no small feat. Bonus: Try to track down the live performances of this song from the 1974 tour, they are sublime — particularly Michael McDonald’s soul drop of the “Where did you get those shoes?” line.