For a man with such an immense and expansive catalog, ranking and boiling down such a compendium to a mere 20 songs could be something bordering on insulting. A lot of deserving tunes would be omitted from view by being left off such a list, but sacrifices have to be made sometimes. And something tells me Sufjan will survive this.
So here we go. My 20 favorite Sufjan Stevens songs, in order and ranked as best as I could rank them in the moment.
20. the dress looks nice on you
album: seven swans
Rare Sufjan brevity that doesn't skimp on the beauty (I will use this word in some form a lot in this post).
19. chicago (adult contemporary easy listening version)
album: the avalanche
Sufjan's (arguably) most popular song that's just two seconds longer than the original, but feels infinitely more relaxed.
18. to be alone with you
album: seven swans
More brevity, but a moment of honesty that can't be denied.
17. from the mouth of gabriel
album: all delighted people ep
The transformation of the song from about 1:23 on is a section of 2 1.2 minutes of music that never stops improving.
16. the predatory wasp of the palisades is out to get us!
album: illinois
A hazy sort of childhood reminiscence.
15. all delighted people (classic rock version)
album: all delighted people ep
The EP's namesake starts out almost ominous, but gradually builds accessible confidence in its place.
14. the tallest man, the broadest shoulders (part I: the great frontier/part II: come to me only with playthings now)
album: illinois
A beat you just can't deny.
13. jacksonville
album: illinois
Another semi-recognizable tune that fills out its sound without overwhelming your ears.
12. impossible soul
album: the age of adz
Twenty-five-plus minutes of an absolute musical experience.
11. i want to be well
album: the age of adz
Not fucking around, indeed.
10. heirloom
album: all delighted people ep
Pretty from the first note.
9. romulus
album: greetings from michigan: the great lakes state
A somber tune of humility and (more) reminiscence.
8. vito's ordination song
album: greetings from michigan: the great lakes state
Starts appropriately with an organ, and gradually builds for six minutes before taking one last full minute to decompose and fade away.
7. the henney buggy band
album: the avalanche
The happiest song Sufjan has ever written and recorded.
6. chicago
album: illinois
The original version of what's likely his most popular song doesn't diminish how good it is.
5. john wayne gacy jr.
album: illinois
A haunting ballad that's so impossibly beautiful, you won't be sure just how you feel about it for a while.
4. holland
album: greetings from michigan: the great lakes state
Arguably the prettiest song Sufjan's ever recorded, a piano and guitars (with an occasional woodwind at the end) strike a great chord in minimalist harmony together.
3. casimir pulaski day
album: illinois
A song about a dying friend that feels at once like a farewell and a recollection of some incredibly personal moments.
2. the transfiguration
album: seven swans
The most overtly religious song on the list, but also one of the most memorable, as it continues to build around its beginning banjo.
1. the man of metropolis steals our hearts
album: illinois
A tribute to Superman couldn't be anything less than super, and so it is.