- "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. It becomes even more poignant in the light of Carrie & Lowell, much of which has to do with Sufjan's difficult relationship with his now deceased 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”
"There's blood on that blade
- The narrator of "Death With Dignity" ruminates on the inevitability of death throughout most of the song, before finally forgiving his absent mother and trying to understand why she made the choices she did.
- The album culminates in the penultimate song "No Shade In the Shadow of the Cross" which depicts him coping with his mother's death by doing lots of drugs, having lots of sex, and hurting himself. One of the most heartbreaking lyrics of the album is found in this song.
Fuck me, I'm falling apart."
- Special mention goes to the live version of "Blue Bucket of Gold". It ends with a 10+ minutes long, post-rock outro that slowly builds up into a fantastical light show. In some videos of the performance, Sufjan almost seems to be crying into the mic.
Tear Jerker / Sufjan Stevens
Hell, just about anything by this musician is pretty damn sad. He has a knack for making heartbreakers.