In the song “Absolutely Sweet Marie,” Bob Dylan famously wrote, “to live outside the law, you must be honest.” Over the years, many musicians have put that axiom to the test, most caught up in circumstances that were due to their regrettable behavior. Still, the music industry has never been the stuff of well behaved individuals. It’s made by and for insurgents for insurgents and rebels with and without a cause. Here then is a list of 16 artists, renegades and rapscallions who served time in the slammer and found it linked to their legacies.

Here is the list of 16 artists

1. David Allan Coe
While others may have claimed to be an Outlaw, Coe lived it to the hilt. First sentenced to reform school at the tender age of nine, he was later convicted on a string of charges, including robbery and possession of pornography. He spent the greater part of 20 years behind bars, furthering his rowdy reputation early on. Little wonder then that following his release, his 1970 debut was dubbed Penitentiary Blues.

2. Jim Gordon
Gordon’s extensive drumming credits included work with Eric Clapton and Derek and the Dominos, with whom he helped pen the iconic classic “Layla.” However, he was also deeply troubled, a victim of schizophrenia that gradually worsened over the years. The illness eventually debilitated him, and in 1983 the voices in his head convinced him to fatally stab his mother. Convicted of murder, he’s currently serving a sentence of 16 years to life in a psychiatric prison.

3. Arthur Lee
One of the great, if somewhat unheralded, musical innovators of the rock era, Arthur Lee led the band Love from their psychedelic start in the mid-‘60s through their last incarnation and glorious revival in the early-2000s. However, Lee was a mercurial and troubled genius, and his 1996 conviction and subsequent 12-year sentence for negligent discharge of a firearm put a temporary cap on his career. Previously convicted of drug charges and assault, California’s three strikes law finally caught up with him, effectively making him a nonentity until he was released from prison after serving five years. He then returned to the helm of Love, but his death from complications related to leukemia silenced him forever on August 2, 2006.

4. John Phillips
It’s hard to imagine that the ‘60s serenader who penned such folk rock classics as “Monday Monday,” “California Dreamin’” and “San Francisco (Be Sure To Wear Flowers in Your Hair)” was really a bad boy at heart. His drug dependence severely curtailed his creative energies after the breakup of the Mamas and the Papas and even led to daughter Mackenzie Phillips charging him with incest, an accusation that some still doubt. In 1981, Phillips was convicted of drug trafficking, but eventually his sentence was reduced to only one month served for the charge he faked drug prescriptions with the help of a local pharmacist. He died on March 8, 2001 from heart failure.

5. Steve Earle
Back in the day, Steve Earle wasn’t exactly a model citizen. Aside from his decided lack of marital fidelity, his drug problems seemed certain to hand him an early death sentence. In many ways, his succession of arrests for possession of heroin and cocaine in 1993 and 1994 might have saved his life. He served 60 days and used it constructively by writing what would become his breakthrough album Train A Comin’. He later spent time in rehab, and to date, has managed to stay straight. It’s nice to find him still on the Copperhead Road to recovery, so to speak.

6. GG Allin
Punk bands seem like prime suspects when it comes to making trouble and then finding themselves in trouble as a result. Even so, the late GG Allin was an extremist who engaged in self-mutilation and attacks on audience members during his stage shows. His disturbing songs centered around such topics as misogyny, pedophilia and racism, all in an attempt to make music that was “dangerous.” (His description, not ours.) It’s little wonder then that he eventually acted on those sadistic sentiments. An assault on a female fan led her to charge him with rape and torture, resulting in 16 months behind bars. Allin, however, insists he did nothing more than cut her, burn her and drink her blood.

7. Sid Vicious
Sid also lived the punk ethos to an extreme. On the morning of October 13, 1978, he stabbed his girlfriend Nancy Spungen in New York’s Chelsea Hotel. Although he claimed he didn’t mean to kill her, he was later arrested and sent to Rikers Island. Released on February 1, 1979 after serving barely two months of his prison term, he died the next day of a heroin overdose.

8. Tupac Shakur
The late Tupac Shakur was not one for courting good luck. Charged with sexual assault in 1995, he was the victim of a hit the day before the verdict was scheduled to be announced. Shot five times, he went into the courtroom in a wheelchair, although that did little to win the jury’s sympathy. He completed eleven months of his sentence and even managed to get married and release an album, the aptly titled Me Against the World, while still in the slammer. Tupac was released in October of that year after record mogul Suge Knight posted a $1.4 million bail in exchange for 2-Pac’s promise to record three albums for Knight’s Death Row record label. That wasn’t the end of his troubles, however. Although he successfully sued the Oakland Police Department for police brutality when they roughed him up after a jaywalking incident, his encounters with gang violence and rival factions eventually did him in. The historic rapper died from gunshot wounds less than a year after his release from prison.

9. James Brown
The late Godfather of Soul was no stranger to the big house and his infamous tangles with the law—including a widely publicized car chase—found him getting down in the prison yard twice. On each occasion, first in 1949 on a charge of burglarizing parked cars and then again in 1988 on multiple counts of resisting arrest, possession of illegal drugs, assaulting a police officer and various traffic violations, he spent three years in jail.

10. Merle Haggard
Merle Haggard was a genuine outlaw before the Outlaw was used as a term in country music. In 1957, he tried to rob a tavern in Bakersfield, a scenario that seems like an ideal premise for one of his songs. After trying to escape his Bakersfield jail cell, he was transferred to San Quentin where he was incarcerated for three years. Haggard said it took him awhile to get used to being free and, at times, he actually wanted to return.

11. Rick James
Rick James never seemed worried about having a bad image. He was awaiting sentencing for kidnapping and assault at Hollywood’s St. James Club and Hotel when he was arrested for holding another woman hostage and assaulting and raping her for the better part of a week while smoking crack cocaine.

12. Chuck Berry
As one of the fathers of rock ‘n’ roll, we’d expect the late great Chuck Berry would be guilty of some, shall we say, indiscretions. Early on, he spent time inside the jailhouse for armed robbery, but at the height of his career, Berry was sentenced to five years for bringing an underage girl across the Mexican border. He served 20 months, but further legal woes were yet to come. In 1990, he was sued by several women who claimed he had installed cameras in a restaurant bathroom so that he could gawk at them in compromising situations. A police raid on his home turned up videotapes of several women, including a minor. Marijuana was also found, leading to drug and child abuse accusations. Berry eventually pleaded guilty to a misdemeanor and was given a six month suspended sentence and two years of probation. In 2000, he was back in court after being sued by his former piano player Johnnie Johnson, who claimed his former boss had denied him royalties for songs the two had supposedly co-written. Sadly, it seemed that the man who wrote “No Particular Place To Go” couldn’t stay out of one place in particular—the courtroom.

13. Phil Spector
As the years went on, it became evident that the inventor of the so-called Wall of Sound was more than a little unhinged (evidenced by trivialities like wearing those outlandish wigs and his more serious penchant for brandishing guns in the studio). Still, his conviction for killing actress Lana Clarkson in 2003 was somewhat unexpected, if for no other reason than Spector made a foolhardy attempt to cover up the crime. It made the same sort of tabloid headlines O.J. Simpson had garnered a few years before, but Spector was actually convicted. He’s currently in his fourth year of a 19-year sentence.

14. Ike Turner
Ike Turner was never the most likeable guy, especially after wife Tina revealed the years of abuse he inflicted on her during their time together. His penance came some time later, however, in 1987, when he pleaded guilty to conspiracy to sell cocaine after trying to peddle it to an undercover cop. He served four years and by the time he was released, his career had capsized.

15. David Crosby
David Crosby holds a special distinction, and not just because he’s a two-time Rock and Roll Hall of Fame inductee (for the Byrds and Crosby Stills and Nash, respectively). Nay, Crosby is an anomaly because he somehow managed to avoid doing time for his flagrant drug abuse, but was done in by his reckless behavior instead. In 1982, Texas State Troopers pulled him over and found a gun in his car. Asked why he carried the weapon, Crosby replied simply “John Lennon.” He was subsequently sentenced to nine months in a Texas prison, and although he was forced to shave his long locks and signature handlebar mustache, he did get in some playing time with the prison band.

16. Paul McCartney
Macca’s first solo tour of Japan was abruptly aborted in 1980 when, upon entering the country, police found nearly eight ounces of weed not so discreetly hidden in his suitcase. He spent 10 days in jail, leading some to speculate that he could be detained indefinitely. No doubt he was yearning for “Yesterday” on the day of the big bust.