I’m not great at clever introductions to themed playlists, so here’s a bunch of songs about characters and people I think are super interesting.
Tom Waits – Gun Street Girl
I’ve always viewed Tom Waits as sort of a bizarro Bob Dylan. They share a penchant for genre jumping, raspy discordant vocals, and immersive songwriting that can tell a complete story in around four minutes. “Gun Street Girl” is on the toned-down side of Waits’ catalogue, relying on only a banjo, drum, and cowbell to back Waits’ haunting tale about a man driven to murder by the titular character, the Gun Street Girl.
Wilco- One Sunday Morning
An twelve minute song about lead singer Jeff Tweedy wrestling with religious idealism and a failing relationship with his father. Sad and pretty, I’ve never listened to a song this long so often
Gil Scott-Heron – I’m New Here
“I’m New Here” is the title track from Heron’s final album before his death in 2011. Similar to Otis Redding’s “Sitting On The Dock of the Bay”, “I’m New Here” sounds like an artist coming to terms with life and his own mortality. For a musician so focused on political change (He first gained national acclaim with “The Revolution Will Not Be Televised”), this song is hauntingly personal and a fitting end to a long storied career.
The Mountain Goats – Lovecraft In Brooklyn.
The Lovecraft in the title of the song refers to author H.P. Lovecraft, the weird fiction writer who invented (or discovered if you believe his stories to be fact) Cthulhu. In the song, the narrator (maybe Lovecraft himself) finds himself alone in Brooklyn, xenophobic and afraid of the world around him. Interesting to imagine that an author famed for writing about terrible monsters his whole life would be most terrified of a New York City borough.
Cloud Cult – When Water Comes To Life.
Cloud Cult’s songs are predominantly about the lead singers’ son, who died when he was a toddler. Obviously this has the potential to produce some extremely depressing music, but in “When Water Comes To Life”, Cloud Cult implements an entire string section to back a story about the boy ascending to heaven and finding happiness. The happiest and most beautiful song about infant death that I’ve ever heard (not that there’s much competition).
The Drive-By Truckers – The Living Bubba
“The Living Bubba” tells us about a musician who is dying of AIDS. Rather than succumbing to the disease, he insists on continuing to play shows every night. Poignant without being pretentious and spouting off “life lessons”, “The Living Bubba” is country music at its finest. The song is based in truth, written after the death songwriter of Gregory Dean Smalley, a big part of the Atlanta music scene before his death.
The Hold Steady – How a Resurrection Really Feels
The finale to a sort of concept album, the final track finds protagonist Holly drunkenly crashing into a church. The final cathartic moment involves challenging a priest about how a resurrection really feels.