Great thread, I'll be re-visiting this for a long time...great stuff here.
My "obscure" addition to this list has to be Root Boy Slim & the Sex Change Band. An enigma if there ever was one. Root Boy was discovered on DC radio by Donald Fagen and their debut album was produced by Gary Katz!
You'd never guess with titles like In Jail in Jacksonville, When My Jones Come Down, & their "hit", Boogie 'til You Puke, that you'd be listening to a Yale graduate who was frat brothers w/ George W. Bush!
Insane lyrics that could never be made up - they were LIVED. After you get a smile from the stories, you realize how good the band is also.
After his death in 1993, guitarist Ernie Lancaster stated, "Although Root Boy was only 48, he lived the life of a 200 year old man."
Check them out if you can.
+1 for John Frusciante, Tonio K., & Poe