- "Casmir Pulaski Day". Dear god, "Casimir Pulaski Day".
- This is only enhanced by the fact that most of his songs featuring Christian elements are pretty positive, but this is certainly not.
- "Romulus" is the story of a group of siblings growing up with a distant mother.
- "Chicago" works for the "happy tears" variety, and the fact that it's directly juxtaposed with "Casimir Pulaski Day" enhances the effect, mutually. Play the trumpet solo from either song and... excuse me, I think I have something in my eye...
- "Djohariah" is definitely one, of both the "happy" and "sad" varieties.
- "John Wayne Gacy, Jr".
- "The Predatory Wasp Of The Palisades Is Out To Get Us!", despite the frantic title, is a heartbreaking and gorgeous song about the end of a (possibly romantic) relationship between two teenage boys who were best friends: "My friend is gone, he ran away, I can tell you I love him each day".
- "I Walked." Beautiful melody, heartbreaking lyrics, lo-fi drum machines and synths in the background.
- "Sister Winter" off one of the Christmas albums.
- Depending on which part you're listening to, "Impossible Soul"can bring tears of joy or of sadness. The end is especially heart-rending. "Boy, we made such a mess together..."
- "For the Widows in Paradise, For the Fatherless in Ypsilanti" isn't necessarily sad, but the picture it paints of unconditional love is certainly very moving. Also goes for "To Be Alone With You."
- Despite its comedic title and cheery feel, the second part of "Come on! Feel the Illinoise!" has been known to bring some tears. Appropriate, since Sufjan is singing about crying himself to sleep.
- "I Want to Be Well," which seems to be narrated by someone dying of a terminal illness. The bitter anger and disappointment Sufjan expresses are devastating.
- Carrie & Lowell. Every single second of it. Written while Sufjan was coping with the death of his oft-absent mother and the result is the Sufjan-weeper to end them all.
“Did you get enough love, my little dove?
- One of the worst offenders is "Fourth of July", sung partly from the perspective of his dying mother:
Why do you cry?
And I’m sorry I left, but it was for the best
Though it never felt right”