The Wildman aside, of all the 'outsider' stuff I've heard I'd have to go with the utterly genius song-poem "Junkies and Monkeys" sung by Kay Weaver and written by James Yates. Here's a real audio link (from Irwin's old WFMU show) which starts about 23 minutes in:
http://wfmu.org/listen.ram?show=2898That said, Kathy Fire's "Mother Rage" is just brilliant and I've snuck in into many a compilation for friends.
"Get your rapist hands off my shoulder now,
Damn your sweet smiling mask of care for me.
Fuck your little boy games you charlatan,
I've seen what you've done and I know who you are."mp3 -
http://blogfiles.wfmu.org/BL/0511/im/14_-_Kathy_Fire_-_Mother_Rage.mp3"Heart of the Heartland" kinda forces itself down the old lughole! I must admit to skipping that whenever I've played the Key-of-Z CD.
edit -- do you know Lil' Markie? If not, check out (mp3 link)
"Diary of an Unborn Child" with much more to explore ("Story of an Alcoholic Father" being the 2nd most traumatic song although the videos are just freaky) here:
http://blog.wfmu.org/freeform/2005/10/the_secret_of_l.html