Crazy Mary. A chilling song by the under-appreciated Victoria Williams.
Covered by Pearl Jam on the fantastic Victoria Williams benefit and tribute album Sweet Relieffrom 1992. It’s one of the best sampler albums of the nineties.
FINALLY! Great band!
Has anyone mentioned Suicide Chump by Zappa? A cruelly cynical comment on (supposedly) attempted suicide.
Almost every song wrote by David Berman under the band names Silver Jews or Purple Mountains will qualify. He fought severe depression all his life and wrote very humanly and eloquently about it. He lost the battle last year. The music is wonderful.
That reminds me that there was a song in the early 70’s called “Crazy Annie” that I liked, but nobody else ever heard of. It was about characters from Midnight Cowboy, but I don’t think it was in the soundtrack.
ETA: found it.
Don McLean’s Vincent about Vincent von Gogh, who certainly had his mental problems.
And Men At Work’s Who Could It Be Now is so obviously about paranoia that I cannot believe I’m the first to mention it!
Who can it be knocking at my door?
Make no sound, tip-toe across the floor
If he hears, he’ll knock all day
I’ll be trapped, and here I’ll have to stay
I’ve done no harm, I keep to myself;
There’s nothing wrong with my state of mental health
I like it here with my childhood friend;
Here they come, those feelings again!
You *were *the first to mention it…
…in post #37. 
I wanna be committed, by Sweet.
Twisted Nerve - The Damned
All Hail Me - Veruca Salt
Quadrophenia (entire album) - The Who
Copacabana (OK, deals with the result of a horrible occurrence):
“She’s lost her youth, and she’s lost her Tony, now she’s lost her mind”.
In addition to Jeremy,, Pearl Jam had a bonus/unreleased track titled Dirty Frank, which is about their tour bus driver being a cannibal. The track is very tongue-in-cheek.
And finger in cheek, and thigh in cheek…
Peter Gabriel - “Lead a Normal Life”
Eating with a spoon… they don’t give you knives…
Most of the tracks on Electro-shock blues by Eels would count. Electro-Shock Blues - Wikipedia
E wrote it as therapy while going through a terrible time in his life. I love the last line on the album though; ‘maybe it’s time to live’
Many of the most unsettling examples are courtesy of Melanie, the “Brand New Key” singer. Lots of people sing about being emotionally & cognitively disturbed, but she could convince you you were hearing someone unravelling in front of the microphone:
Even when she wasn’t singing lyrics that specifically referenced being off-balance, it tended to lurk in her music:
Animal Crackers
… of course that was part of the charm. All that personal vulnerability, making you feel like she’d understand your cracked and broken interior parts and stuff.
From “Candles in the Rain”:
We were so close there was no room
We bled inside each other’s wounds
Damn but that’s a great line.
Speaking of Melanie, she also had some fun satirizing the subject in “Psychotherapy.”
Jimmy Buffet - Changes In Latitudes, Changes In Attitudes, “If we weren’t all crazy we would go insane”
King Crimson - Three Of A Perfect Pair, “One, one too many schizophrenic tendencies, keeps it complicated…”