Johnny Paycheck - 11 Months and 29 Days

In 1985, Paycheck was convicted and sentenced to 7 years for grazing some dude's scalp with a .22. Paycheck claimed the act was self-defense. He spent 22 months in prison before he was pardoned by the Governor for this infraction. 
That old judge put a sledgehammer in my hands when he said "I'm gonna send you to Huntsville, shave your face and your head I'm doing 11/29 boys with a cement floor for my bed Busted in Austin, walkin' around in a daze, yes I was Now, I'm sitting in this slammmer, looking out the these bars in a haze but it'll all clear up in 11 months and 29 days, yeah Lord

“To me, an outlaw is a man that did things his own way, whether you liked him or not.   I did things my own way.	”
—Johnny Paycheck

Spade Cooley - You'll Rue The Day

Spade Cooley, whose music is heard in the film The Killer Inside Me stomped his wife to death, just like Casey Affleck did with Alba in the film. He spent some time in the can, and dropped dead of a heart attack the day he was released to perform for the policeman's benevolent society. Cooley's music though, remains an essential chapter in country music, thus gaining him the title of the King of Western Swing. Check out Swingin' The Devil's Dream here. Thanks to musictraveler.blogspot.com for the review.