Hell, just about anything by this musician is pretty damn sad. He has a knack for making heartbreakers.
- "Casimir Pulaski Day". Dear god, "Casimir Pulaski Day"."And He takes and He takes and He takes..."
- This is only enhanced by the fact that most of his songs featuring Christian elements are pretty positive, but this is certainly not, considering it's about a crisis of faith triggered by the death of a loved one.
- "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.
- By the time he gets to the final chorus ("I was ashamed, I was ashamed of her...") it sounds like Sufjan himself is about to start crying (which wouldn't be surprising, if the song is as personal as it seems to be).
- "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...
- "Djohariah" is definitely one, of both the "happy" and "sad" varieties.
- "John Wayne Gacy, Jr".
- "Flint".
- "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.
- One of the worst offenders is "Fourth of July", sung partly from the perspective of his dying mother:
“Did you get enough love, my little dove?
Why do you cry?
And I’m sorry I left, but it was for the best
Though it never felt right”- During live shows "Fourth of July" is played as an acoustic ballad, like the studio version, but during the coda electronica starts kicking in in a post-rock crescendo until Suf shouts "But I'm still alive!". It comes off as sad, angry and moving at the same time. This performance
adds more instrumentation, Illinois-esque horns and a One-Woman Wail, and the result is breathtaking. - 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.
"There's blood on that blade
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.
- "Drawn to the Blood", a song about the narrator being stuck in an abusive relationship that has unfortunately been confirmed to have actually happened. The sheer anguish in Suf's voice as he sings lines such as "How did this happen?" and "What did I do to deserve this?" is nothing less than heartbreaking.
- Although there's a definite sense of apathy in "Should Have Known Better", the real heartbreaker are the lines expressing his ever-weakening attempts to see life's simple beauty.
Don't back down/concentrate on seeing
the breakers in the bar/the neighbor's greeting
my brother had a daughter... the beauty that she brings
illumination. - "The Seer's Tower", a desolate piano piece with an eerily ghastly atmosphere and apocalyptic lyrics.Still I go to the deepest grave
Where I go to sleep alone. - "Enchanting Ghost," in which Sufjan muses on a relationship that seems to be on the way out and encourages the other party to leave him if it's too difficult/stifling to stay. Heartwarming for the compassion and acceptance the narrator shows his lover/friend, but heartbreaking for the sense of good things ending and good love going bad.
- "Redford (for Yia-Yia & Pappou)", a beautiful instrumental piano piece that encapsulates the feeling of standing at the edge of the Earth, musing over your entire life.
- Pretty much all of Planetarium, his collaborative album with Nico Muhly, Bryce Dessner and James McAlister, but the closing track Mercury is the crowner.
- Javelin marks another heartbreaking album about personal loss, with Sufjan mourning his late partner, Evans Richardson. From the return to his classic lush acoustic instrumentals, tired, yet emotional vocal performances, and of course, his poetic, yet frank and vulnerable lyricism throughout — from the overt mourning of "Goodbye Evergreen", to the hopelessness of "Will Anybody Ever Love Me?", to the sheer denial and desperation of "Shit Talk" — it's as haunting and beautiful one can get describing losing the love of your life.
