Niel Innes - How Sweet to Be an Idiot
Isn’t Dear Prudence about Mia Farrow’s sister going a little loopy during the Beatles’ deadbeatery in India?
Liar by The Rollins Band.
I would take the combined catalogs of Nirvana and Alice in Chains, sprinkle in some Pearl Jam, various Chris Cornell songs and a bunch of Gray Matter, then smooth the whole nightmare over with the Soul Asylum catalog. Shake well and top it off with Wrong Way Up.
Depending on the randomization algorithm, you will make it through or you will never come back.
I’d nominate some of Scott Walker’s more recent work, particularly Bish Bosh, which mixes orchestral music with wailing, disturbing sounds and an over-riding sense of depression and foreboding. Not at all easy to listen to [in relation to challenging content, not implying they are shite].
Some of my go-to songs in this ?genre are Eno’s “Third Uncle”, “55 The Law” by the Screaming Blue Messiahs and numerous selections from The Minus Five’s album “The Minus Five”, including “With A Gun”:
*"I’ll kick your sister’s ass
I’m going to take your brother’s face and smash it in the grass
It’s no wonder I am spiral-bound
'Cause I just want to
I just want to be around
Every day when I feel this way
I need somebody to say, “It’s okay”
Shoot some holes in my crow-black sky
Saying, “Life doesn’t really half-suck most of the time”*
From the same album, “Cemetery Row” is a near-genius song that should probably not be listened to by anyone in or near a depressive state. It has one line about “this old house is cold and crowded with half-wits” which for some reason reminds me of the Dope. 
Did I miss a Rolling Stones 19th Nervous Breakdown reference above?
And Wreck-age
Nurse with Wound: Fashioned to a Device Behind a Tree
Current 93: Faust
Throbbing Gristle: Hamburger Lady
Pretty much any song from Jazz Funk Greats by Throbbing Gristle.
Some might feel this way about The Well-Tuned Piano by La Monte Young.
Also the sequel:
“Breakdown” by Tom Petty!
