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Jailhouse Rock: 10 Artists Who Did Hard Time In The Slammer

Nothing earns an musician instant street cred quite like a night or two in the pokey. It's basically a rite of passage -- a guarantee that if you sign up for the public eye, you will, indeed, screw it up at least once in order to delight us with your antics.

From the likes of good ol' boys like Merle Haggard and Johnny Cash to rock legends like Paul McCartney, it's easy to name the artists who've done short stints in the grey-bar hotel. Every once in a while, though, an artist will jump the proverbial gun and make an ill-advised leap from lowly misdemeanor to hardcore felony, all with one swift kick of someone else's ass.

Instead of seeing an increase in record sales, these artists get to see the inside of a prison cell for the next, oh, three or so years. Because mugshots are awesome, here's a list of the top ten artists I was surprised to see as members of the hard-time club. (Rick James is not on this list for obvious reasons, y'all. We all saw that coming a mile away.)

10. Billie Holiday Lady Day, as Holiday was known to her friends, was not only a jazz great, but also a jailbird. Holiday did a couple of rounds in the pokey thanks (in part) to a shitty childhood and a drug habit.

In May 1929, both Holiday and her mother were sent to prison after the brothel they were working at was raided. Holiday spent about six months in the hoosegow, and was 14 at the time. She was arrested again in '47 for possession of narcotics and sent to Anderson Federal Prison Camp for an 8-month stint.

9. GG Allin The 'Merican punk-rock singer-songwriter was known for spitting lyrics about topics like pedophilia and racism. He also relished in performing at concerts where he'd incorporate live "transgressive" acts (think shit like self-mutilation, covering himself in his own feces, and attacking the audience as the equivalent of "transgressive" in this equation), so it should come as no surprise that Allin also found himself in a heap o' trouble, and often.

In late '89, Allin was arrested and charged with assault with intent to do great bodily harm on a female acquaintance. Allin admitted to cutting her, burning her, and drinking her blood as part of a really fucked-up sexual encounter. He took a plea-bargain and was sent to prison for felonious assault for a couple of years as punishment.

8. Beanie Sigel In very recent news (think this month), Sigel pleaded guilty to illegally possessing Percocet, which landed him in prison for a term of 6-23 months. That's on top of the two years of federal time he's already serving for failing to pay around $348,000 in taxes. Ain't that a bitch.

The more recent sentence stems from an incident in Philly in 2012 when the car Sigel was riding in was pulled over by the cops. Police searched the car and found a loaded .30 caliber handgun, $4,600 cash, and Codeine syrup. Sigel was the passenger and was passed the fuck out, but he's a convicted felon and that whole loaded-gun thing is a huge no-no when you've got a rap sheet, apparently.

 

7. Snow Darrin Kenneth O'Brien, or Snow, is responsible not only for that little white-boy reggae gem known as "Informer", but also for an assault that served him up a year sentence.

The Canadian reggae artist (WTF) only did about eight months in jail on the year-long charge. I'd tell you more, but I don't really have a clue about the details. I just really wanted to bring up "Informer." I'm pretty sure I can still recite every lyric, and I know you're impressed.

6. Steve Earle The singer-songwriter, whose songs have been recorded by the likes of Travis Tritt, Vince Gill, Shawn Colvin, and Emmylou Harris, has found infamy not only from his lyrics but also his trouble with the law.

In 1993, Earle was arrested for possession of heroin. He quickly followed that up by a '94 arrest for possession of cocaine and weapons. Earle was sentenced to a year in prison after he admitted possession, but failed to appear in court to answer the charges. He was released after about 60 days.

5. Johnny Paycheck Paycheck didn't just inform jobs that they could shove it -- he also got into a heap of trouble for a fight with a stewardess, an alleged assault on a 12-year-old girl, and got popped for check forgery.

Ol' Paycheck didn't face any real hard time, however, until 1985, when he was drinking at a bar in Hillsboro, Ohio, during a visit to his mama on Christmas. (You can't make this shit up.)

The details are murky at best, but somehow Paycheck became enraged after being offered a home-cooked meal of turtle soup and deer-meat, and shot bar patron Larry Wise with a .22, grazing his head. After three years of appeals, Paycheck was finally sent to a medium-security prison for a couple of years.

 

Jailhouse Rock: 10 Artists Who Did Hard Time In The Slammer

4. Big Lurch This entire story makes my stomach turn in a bad, bad way, so you've had your warning. Don't read on if you're wasting time at lunch.

Texas rapper Big Lurch (or Antron Singleton, as he's now known in the penal system) is currently serving a life sentence for murdering and eating his roommate while under the influence of PCP in Los Angeles in 2002. Folks, please stick to cannabis. It's less zombie-inducing.

The rapper, who worked with guys like Lil Keke, Mac Dre, and Mystikal (prior to the whole cannibal thing) was found in April 2002 wandering the streets of Lala-land naked and covered in blood.

When cops searched his apartment, they found Tynisha Ysais with a three-inch blade broken off in her shoulder, and teeth marks on her face and lungs, which had been torn from her body. The medical examiner also found human flesh in his guts that wasn't his. Gag.

3. Chuck Berry Apparently the man who brought us "Johnny B. Goode" just wanted to be a tad bit bad. This musical pioneer did a short stint in prison in 1944 for the robbery of a bakery, a barber shop, and a clothing store. (I hope he stole sticky buns.)

The trouble didn't stop with robbery, though. Berry was arrested in 1959 under the Mann Ac after the allegation that he had sexual intercourse with a 14-year-old, who he had transported over state lines to work as a hat check girl in one of his clubs. She was later found to be working as a prostitute.

Berry was convicted and sentenced to five years in prison. He ultimately served around a year and a half.

2. Ronald Isley Ronald Isley -- of the Isley Brothers fame -- was sentenced to about 37 months in prison is 2008 for the lamest reason known to man: tax evasion.

Isley was convicted of five counts of tax evasion and one count of willful failure to file a tax return in 2007, receiving not only his prison sentence, but also a fine of nearly $3.1 million. Hardly hardcore until you consider that the charges held a maximum sentence of 26 years. Mr. Biggs ultimately did about two and a half years' time.

 

1. David Crosby This two-time Rock and Roll Hall of Fame inductee with the Byrds and Crosby, Stills, Nash & Young has also earned himself a couple of months of prison time thanks to a drug habit and a penchant for weapons.

In '82, Crosby spent about nine months in the Texas prison system for a slew of drugs and weapons charges, including possession of heroin and cocaine. He's been charged with a bunch of other crap in the years following his prison stint, but has managed to dodge jail time for all of the more recent incidents.



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