Five musicians who served jail time in their prime – for drug smuggling, armed robbery, weapons charges and more…

“It’s no fun when that iron door clangs shut on you.” – Deputy Barney Fife to a group of youngsters on a tour of the Mayberry jail.

If you listen to rock & roll really closely, you may be able to hear the distant sound of Barney Fife’s iron door clanging shut. That sound is, as Barney warned, “the last stop on the road to crime.” At its roots (and its best), rock & roll is rebel music, a middle finger extended to polite society and a Pied Piper provocation for listeners to follow suit.

Johnny Cash at San Quentin

Sometimes that rebellion goes too far and you end up in Mayberry jail with Otis Campbell for a cellmate—if you’re lucky. If you’re not, you end up in a SuperMax prison with a wannabe Hannibal Lecter. Of course, sometimes you’re just a violent or dangerous creep and you should be locked up (see: Glitter, Gary; Spector, Phil; Manson, Charles).

The following members of rock & roll’s cosmos—and, by that, I am referring to both practitioners and progenitors—are just a few who knew well the sound of clanging iron. As you read through this annotated list, imagine “Jailhouse Rock” by Elvis Presley playing in the background—the only song, perhaps the only piece of pop culture, to ever make prison seem like a whole lotta fun.

Johnny Cash

Despite his renown as a friend to the incarcerated—see the single “Folsom Prison Blues” and the album Live at San Quentin—Cash never actually served a prison sentence. This does not mean he never saw the inside of a jail cell. He was, in fact, arrested and jailed on misdemeanor charges on seven different occasions, but was often released within a day or two. The most widely publicized of his alleged lawbreaking occurred on Oct. 4, 1955, when he was arrested in El Paso Texas while on tour. El Paso being directly across the Rio Grande from Juarez, Cash was suspected of having smuggled heroin into Texas from Mexico. However, he “only” had 688 hits of amphetamines and 475 hits of tranquilizers in his possession (actually, inside his guitar case). Amazingly—given his many previous arrests—the authorities let him go because these were prescription drugs, not contraband. Here’s Johnny Cash in prison…as a performer. This is from the legendary concert at San Quentin State Prison.

Chuck Berry

In December 1959, the rock & roll star, who by then had released such hits as “Maybelline,” “Roll Over Beethoven” and “Johnny B. Goode,” was arrested under the Mann Act (aka, the “White Slave Traffic Act”) after it was alleged that he had sex with a 14-year-old waitress, Janice Escalante, whom he had transported across state lines to work as a hatcheck girl at his St. Louis nightclub. The Mann Act was a selectively used tool, sometimes aimed at famous black men (like Berry and the boxer Jack Johnson) but also at political undesirables like Charlie Chaplin and Frank Lloyd Wright. Berry was convicted in March 1960, fined $5,000, and sentenced to a five-year prison term. He appealed the decision, claiming the judge’s racially-charged comments prejudiced the jury against him. Amazingly—given the racist tenor of the times—he won his appeal and was given a second trial, which ended in June 1961 with another conviction and a three-year term. His second appeal failed and he ended up in prison from February 1962 to October 1963. During the long legal ordeal, Berry continued performing and recording; the last single released before the iron door clanged shut was “Come On.”

Here’s the maestro live, backed by (what?!) Gerry and the Pacemakers, in 1964. If nothing else, Chuck looks ecstatic to be out of prison:

Merle Haggard

Merle Haggard 1961. PD

Haggard was a chronic hellraiser in his late teens and was sent to reform school for his petty crimes (Preston School of Industry). Eventually, he was arrested and convicted for armed robbery when he was 20 and sent to San Quentin State Prison. He continued to be a hellraiser even there, running a gambling and an alcohol operation out of his cell. A guard caught him one day, visibly intoxicated, and he was thrown into an isolation cell by prison authorities for a week. This cell was part of the “Shelf,” known as “a jail within the prison.” The Shelf was located on the same cellblock as Death Row. The experience scared Haggard straight. In particular, he had conversations with Caryl Chessman, the legendary Death Row inmate who’d become an international cause celebre and bestselling author. Chessman advised the young hellion to develop his mind and talents. Many years later, Haggard credited Chessman’s example with putting him on the straight and narrow. As soon as he got off the Shelf, he volunteered to work at the jute plant, took high school equivalency courses and played with the prison’s country band. At his second parole hearing in 1960, Haggard was given a five-year sentence, which included two years and nine months in jail, two years and three months on parole; he left prison ninety days later and never went back. Nearly half a century later, Haggard told Larry King, “I’m 67 years old, and I was 20 at the time. I still have nightmares [about the seven days next to Death Row] There is nothing, not even a country music career, worth going to San Quentin for.”

The experience scared Haggard straight. In particular, he had conversations with Caryl Chessman, the legendary Death Row inmate who’d become an international cause celebre and bestselling author. Chessman advised the young hellion to develop his mind and talents. Many years later, Haggard credited Chessman’s example with putting him on the straight and narrow. As soon as he got off the Shelf, he volunteered to work at the jute plant, took high school equivalency courses and played with the prison’s country band. At his second parole hearing in 1960, Haggard was given a five-year sentence, which included two years and nine months in jail, two years and three months on parole; he left prison ninety days later and never went back. Nearly half a century later, Haggard told Larry King, “I’m 67 years old, and I was 20 at the time. I still have nightmares [about the seven days next to Death Row] There is nothing, not even a country music career, worth going to San Quentin for.”

“Sing Me Back Home” was one of several songs Haggard later wrote about his prison experience. The Grateful Dead regularly performed this song (and another Haggard song, “Mama Tried”) in concert. Here is Haggard singing the song:

Arthur Lee

Arthur-Lee-Nov-5-1977-by-Ed-Perlstein- Wiki-Fair-Use

Arthur Lee Nov 5, 1977 – by Ed Perlstein

Arthur Lee could have been a contender, if he could have curbed his appetite for self-sabotage. His band, Love, ruled Sunset Strip in the mid-1960s. They were more popular than the Byrds and the Doors, two bands that played the same L.A. clubs and waged a sort of friendly competition. Love, an interracial band—unusual for its time—was the first of this trio to sign a record deal, get their own billboard on Sunset Strip, release a hit single (a cover version of Bert Bacharach’s “My Little Red Book”) and appear on American Bandstand. They were poised for stardom. But Lee, the guitarist, singer and primary songwriter for the band, was notoriously difficult to get along with, and he refused to tour. After their third album, Forever Changes (1967)—generally regarded as one of the finest ever American rock recordings—the members of Love had gone their separate ways. Lee assembled a new lineup of Love but they were never as good, and his own solo career failed to take off. He got deep into drugs, then petty crime and even briefly ended up homeless. The Wheel of Fortuna really nailed him in 1996, when he was convicted of “negligent discharge” of a firearm. Because of a recently enacted “three strikes law,” Lee was given a 12-year sentence. On December 12, 2001, Lee was released from prison, having served more than five years of his original sentence. A federal appeals court in California reversed the firearms charge, ruling the prosecutor at Lee’s trial was guilty of misconduct.

In the song, “Live and Let Live,” from Forever Changes, Lee seemed to anticipate what would happen to him in the coming decades.

He sings, “Served my time / served it well / You made my soul a cell…”

Here is Lee singing the song in Greece in 2003, backed by Baby Lemonade. Sadly, three years later, Lee would be dead to cancer.

David Crosby

Everyone knows the trajectory of Crosby’s career: After leaving (or being kicked out of) the Byrds, he embarked on a solo recording career (see “Almost Cut My Hair”) and then joined Crosby, Stills and Nash, which expanded to include Neil Young. Meanwhile, the wide-faced, walrus-mustached Crosby always had a huge grin on his face and really squinty eyes. There was a reason for this: Drugs. Lots of drugs. By the early 1980s, one of his friends told People magazine, “David [freebases] pretty much from when he gets up to when he collapses,” a friend said in the same article. “I think you can safely say that David has smoked up everything he owns — all the cars, everything.” It was probably, therefore, inevitable that he would be arrested, which he was in Dallas in April 1982 for not only possession of cocaine but for carrying a .45-caliber handgun, which he claimed he bought after John Lennon was murdered in late 1980. As part of a plea bargain, Crosby agreed to go to a rehab facility but, after two days, walked out. He was re-tried, convicted and sentenced in Aug. 1983 to five years for the coke, and three years for the gun. After many failed appeals, he went to prison in March 1986 and was paroled in August of the same year.

Here’s a clip showing Crosby with Stills and Nash, during his drug years.

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