7
Skip James Cuts a Woman in Half ("22-20 Blues" - 1931)

"22-20 Blues" tells the tale of a woman who just won't get her act straight. See, Skip James sent for her, on several occasions, and yet she didn't show up! The brazen audacity! Of course, in the world of blues, there's only one way to deal with minor punctuality issues: brutal, brutal murder.

Big on punctuality.
A Few Choice Quotes
Sometimes she gets unruly;
An she act like she just don't wanna do;
But I get my 22-20;
I cut that woman half in two;

Source.
Your .38 Special;
Buddy, it's most too light;
But my 22-20;
Will make ev'rything, alright;
Shooting your woman with a mere .38 pistol? That's for pussies. Ironically James soon found himself humbled when Robert Johnson recorded a far more popular version of his song. The only real change Johnson made? He upped the caliber and named it the "32-20 Blues." It was all about the gun size with those boys.
6
Lucille Bogan Fucks Corpses ("Shave 'Em Dry" - 1935)

Looking at a picture of Lucille Bogan, it's easy to imagine her as the motherly type, making breakfast and scolding you for your dirty mouth; but in reality beneath the modest exterior was the queen of the "dirty blues," and the writer of such classics as "Sloppy Drunk Blues," "Tricks Ain't Walkin' No More" and the "Bull Dyke Women's Blues."

Her most infamous song was "Shave 'Em Dry," a three-minute ode to her own humping prowess so filthy it would Lil' Kim blush.
A Few Choice Quotes
I got nipples on my titties, big as the end of my thumb;
I got somethin' between my legs'll make a dead man come.
You know it's a good song when the first two lines reference necrophilia and giant freak nipples.
Say I fucked all night, and all the night before baby;
And I feel just like I wanna fuck some more.
You know how people ask which dead celebrity you'd like to meet if you could? We submit Lucille Bogan for your consideration.

Move over Gandhi! You shithead!
Now your nuts hang down like a damn bell sapper;
And your dick stands up like a steeple;
Your goddamn asshole stands open like a church door;
And the crabs walks in like people.
Er, actually we take that back.
5
King Solomon Hill Sentences a Woman to Devil Rape ("Whoopee Blues" - 1932)

"Whoopee Blues" is another song about a poor blues man having to deal with a mean mistreating woman. King Solomon Hill isn't one to settle for mere murder though, he wants his woman sent to hell to do it with the Devil--which strikes us as just a tad judgmental. We're no theologians, but we're pretty sure slashing your girlfriend to death with a razor is pretty much a one-way ticket to becoming Satan's bitch.