Lil Boosie is a free man after serving five years in prison on drug charges, and that got us at XXL thinking—what are some of the longest prison bids in history? Hip-hop has long had an unfortunate association with the prison system, with some of its most high-profile stars—Lil Wayne, T.I., Pimp C, Tupac—heading to the pen while their careers were at their highest points. But it's not always easy to pinpoint the lengths of some of the terms; incomplete prison records, inaccurate data, prison escapees—we're looking at you, O.D.B.—all factor in. So we've compiled a list of some of the longest single bids in hip-hop's history, from C-Murder's in-and-out convictions to Max B's dubious sentence to Big Lurch's moment of insanity. Check them out. —XXL Staff (@XXL)

Ed. Note: This story was originally published Mar. 13, 2014. All information has been updated as of Aug. 1, 2014.

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DMX

Incarcerated: December 16, 2010
Released: July 18, 2011
Amount Of Time: 214 days
Charge: Probation violation
What Happened: Another case of, "Which time was that?" DMX is no stranger to the pen, and his probation violation was another feather in his cap.

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Gucci Mane

Incarcerated: November 12, 2009
Released: May 12, 2010
Amount Of Time: 181 Days
Charge: Probation violation
What Happened: He's been busted so many times it's hard to keep track of which one this even was, but Gucci has had a 2005 aggravated assault case that's been the gift that keeps giving, sticking him with multiple six-month bids for probation violation along the way. However, it's his current charges—that he threatened police with a gun—that may wind up as his longest sentence; he's been locked up since September, and may face as many as 20 years in prison for this one.

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Tupac

Incarcerated: February 14, 1995
Released: October 10, 1995
Amount Of Time: 239 Days
Charge: Sexual Assault
What Happened: Tupac was actually cleared of the majority of the charges in this case where a woman claimed she was raped by him and a number of other men in a hotel room, but he picked up a year and a half for "unwanted touching of the buttocks," the only charge that stuck.

2Pac


Amount Of Time: 241 Days
Charge: Criminal possession of a weapon
What Happened: Wayne got busted in New York with a gun, and was sent to Riker's for a year to wait it out.

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Cassidy

Incarcerated: June 17, 2005
Released: March 2, 2006
Amount Of Time: 258 Days
Charge: Involuntary Manslaughter
What Happened: After initially facing a murder rap in the 2005 killing of one man and the attempted murders of two others, Cassidy waived his right to trial by jury and submitted himself to the mercy of the judge, who declined to convict him of first degree murder.

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Lil Kim

Incarcerated: September 19, 2005
Released: July 3, 2006
Amount Of Time: 287 Days
Charge: Perjury and conspiracy
What Happened: Shootings outside Hot 97 happen more often than the famed NYC radio station would probably like to admit, but it wasn't necessarily her involvement in the shooting so much as her lying to a grand jury about it afterward that landed the Queen Bee behind bars. Video surveillance uncovered the truth, and there wasn't much else Kim could do about it.

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T.I.

Incarcerated: May 26, 2009
Released: March 26, 2010
Amount Of Time: 304 Days
Charge: Federal weapons charges
What Happened: Tip was facing 10 years on federal weapons possession charges, but a plea deal with prosecutors kept the Kang out of the pen for an extended period; not only that, it brought a lot of scrutiny to what, exactly, he had to give up in order to keep those nine years.

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Tony Yayo

Incarcerated: January 1st 2003
Released: May 25, 2004
Amount Of Time: 508 Days, minus January 8th, the day he was paroled on the first charge; he returned to prison the next day on the second charge
Charges: Weapons possession and forged passport
What Happened: Just as G-Unit was about to blow, Yayo went into the can after cops found a gun in a car with 50 Cent, Lloyd Banks and Yayo. The other two got off scott free, but Yayo got busted on an old warrant and picked up a year in jail; the day he got out, while meeting with his parole officer, he accidentally provided a passport that was forged as documentation. The next day, he found himself right back in prison.

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BG

Incarcerated: July 18, 2012
Released: Still Ongoing
Amount Of Time: 744 Days
Charge: Felony gun possession and witness tampering
What Happened: A traffic stop in 2009 turned up three guns—two of which, as well as the car, were stolen—and as BG was a convicted felon at the time, mandatory prison was on its way. But when the cops found out that one of his associates in the car confessed to owning the guns at BG's request, they tacked on tampering to the charge. The former Cash Money man was sentenced to 14 years.

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Ja Rule

Incarcerated: June 8, 2011
Released: May 7, 2013
Amount Of Time: 699 Days
Charge: Attempted possession of a weapon and tax evasion
What Happened: Murder Inc was just the label name, right? Ja was busted the same night as Wayne for attempted weapons possession, and with his many priors he didn't get off as easy as Weezy F. Baby did. While he was locked up, he also got hit with 28 months for tax evasion, but the judge allowed that to be served concurrently with his gun charges. Whew.

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Ol' Dirty Bastard

Incarcerated: November 28, 2000
Released: April 7, 2003
Amount Of Time: 860 Days
Charge: Narcotics possession, traffic violations, fleeing rehab, becoming a fugitive, etc.
What Happened: O.D.B. kind of went off the rails towards the end of the 1990s, with Wu-Tang's most eccentric member being arrested a series of times in just over a year. The initial charge which put him behind bars stemmed from a traffic bust where cops found crack and marijuana on him. Then he failed to show up in court and was sentenced to a year in rehab for making terroristic threats and wearing a bulletproof vest as a convicted felon. A few months after, he was kicked out of rehab, then sentenced again to more rehab. And then he disappeared, running away from the facility and becoming a fugitive, only to show up on stage for Wu-Tang's record release party for The W, only to be re-arrested a week later at a McDonalds, where he was finally sentenced to 2-4 years in prison for the variety of offenses.

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(Photo by Bob Berg/Getty Images)

Prodigy


Incarcerated: October 8, 2007
Released: March 7, 2011
Amount Of Time: 1246 Days
Charge: felony gun possession
What Happened: He already had gun charges in the past, and an illegal u-turn on the highway caused a patrolman to search his vehicle and find another one as well. He kept busy while locked up, though, writing a book on his life's experiences.

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Pimp C

Incarcerated: January 2002
Released: December 30, 2005
Amount Of Time: Approximately 1445 days
Charge: Probation violation related to an aggravated assault charge
What Happened: Pimp got into an argument at a mall with a woman, where he apparently flashed a gun, and was arrested. When he fell behind on community service, a judge sent him to jail, much to the anger and protest of the hip-hop community who, led by Bun B, started the Free Pimp C campaign.

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Lil Boosie

Incarcerated: November 9th, 2009
Released: Mar. 5, 2014
Amount Of Time: 1577 Days
Charge: Possession of marijuana, violating parole, and conspiring to bring drugs into a penal institution
What Happened: Boosie was busted in 2009 on his third weed possession charge, which landed him with a two-year bid, which the judge then doubled when Boosie violated his probation. Everything was doubled again when he pleaded guilty for trying to have drugs smuggled into his prison cell—this while he was fighting a murder rap for the 2009 killing of another local rapper. He stared down the death penalty and won the case, and celebrated with his release last week after five years behind bars.

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Max B

Incarcerated: September 3, 2009
Released: Still Ongoing
Amount Of Time: 1793 Days
Charge: Convicted of conspiracy to armed robbery, kidnapping, aggravated assault, and murder
What Happened: A hotel robbery gone bad, according the Feds. Max B wasn't even there—no one disputes that—but New Jersey courts ruled that he was part of a conspiracy that resulted in the shooting death of a man in 2006, after Biggaveli's on-again-off-again girl and another acquaintance shot him while attempting to rob his friend. He may not have been around, but Max B wound up picking up 75 years after being pinned in the conspiracy.

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C-Murder

Incarcerated: August 14, 2009
Released: Still Ongoing
Amount Of Time: 1813 Days
Charge: Second degree murder
What Happened: He's actually served longer than that, but a re-trial following his initial conviction in September 2003 placed him on house arrest until the second conviction in 2009. In January 2002, a 16-year-old at a nightclub was caught up in an altercation outside the venue, when he was beaten and shot to death, allegedly by C-Murder. The case has caused so much controversy—two convictions, the Supreme Court getting involved, the Louisiana NAACP investigating jury deliberations—that "Free C-Murder" became another campaign to rally around for much of the hip-hop community.

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Bump J

Incarcerated: November 13, 2008
Released: Still Ongoing
Amount Of Time: 2087 Days
Charge: Bank Robbery and weapons charges
What Happened: Bump and another man walked into a Chicago bank and emptied it of $100,000 in 2007, before going out on the run. Bump would eventually get arrested during a traffic stop after more than a year and cop a plea deal, taking seven years for the heist.

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Slick Rick

Incarcerated: June 24, 1991
Released: June 4 1997
Amount Of Time: 2172 Days
Charge: Attempted murder and weapons charges
What Happened: Just as his career was picking up, Rick got busted for shooting his cousin/bodyguard who had been attempting to extort him. Unfortunately, Rick also shot an innocent person standing nearby, and a police chase resulted in Rick picking up attempted murder charges and serving five years.

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Mystikal

Incarcerated: January 15, 2004
Released: January 14, 2010
Amount Of Time: 2191 Days
Charge: Sexual battery, extortion, and failure to file tax returns
What Happened: Once one of the biggest rappers in the game, Mystikal threw it all away after an attack on a stylist turned really ugly. He and two of his bodyguards were convicted of being forced into sexual acts by the trio, which landed the MC very firmly behind bars for the better part of a decade.

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Remy Ma

Incarcerated: March 27, 2008
Released: Aug. 1, 2014
Amount Of Time: 2318 Days
Charge: Assault, illegal weapon possession and attempted coercion
What Happened: She shot her friend in the stomach after an argument, which derailed a promising career.

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Mysonne

Incarcerated: July 31, 1999
Released: July 5, 2006
Amount Of Time: 2531 days
Charge: Armed Robbery
What Happened: Just as he was about to drop his debut studio album after a string of highly successful mixtapes, Mysonne felt the hammer fall with two convictions of armed robbery stemming from two separate cab driver robberies in 1998, both of which he says he was innocent of. Fourteen years came down from the judge, and even though he only wound up serving seven, he never really recovered, career-wise.

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Flesh-N-Bone

Incarcerated: September 22, 2000
Released: July 13, 2008
Amount Of Time: 2851 Days
Charge: Assault with a deadly weapon and probation violation
What Happened: It's a really sad story, and not one that is fun from any side. After a series of legal issues and incidents involving the brandishing of firearms, Flesh-N-Bone was eventually locked up after pulling a loaded AK-47 on a former friend and aimed it. The judge was able to show some mercy, pointing out his sadly extensive history of being abused as a child, but still sent him away for 12 years to straighten out.

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Shyne

Incarcerated: June 1st 2001
Released: October 6, 2009
Amount Of Time: 3049 Days
Charge: Attempted murder, assault, and reckless endangerment
What Happened: Ten years in jail is an awful long time, but that's what Shyne got for his role in a wild shooting at a Manhattan nightclub that resulted in Diddy and then-girlfriend Jennifer Lopez fleeing in a car before being pulled over. Three people were injured that night, and Shyne took the rap, only to get deported upon being released in 2009.

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Turk

Incarcerated: April 1, 2004
Released: October 12, 2012
Amount Of Time: 3116 days
Charge: Second degree attempted murder
What Happened: The Hot Boys didn't have the best track record when it came to staying out of prison. Cash Money's stable of young talent was busted up again when Turk was arrested for his involvement in the shooting of a Memphis police officer. He was eventually arrested on weapons charges and other violations, but it was the attempted murder rap that got him his 14 years, of which he served almost nine.

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Chi-Ali

Incarcerated: March 5, 2001
Released: August 28, 2012
Amount Of Time: 4102 days
Charge: Manslaughter
What Happened: In January of 2000, the Native Tongues rhymer was involved in the death of his brother-in-law and went out on the run, leading authorities on a year-plus-long chase that ended in March of the following year, when he was finally apprehended and charged with the killing. He wound up on America's Most Wanted in the meantime, and was hit with 14 years for the crime.

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Big Lurch

Incarcerated: April 10, 2002
Released: Still Ongoing
Amount Of Time: 4496 days
Charge: Murder, Torture and aggravated mayhem
What Happened: It's like a walking advertisement against PCP. The Bay Area rapper was doing perfectly fine for himself until he got a little too fucked up on dust, cooked up his girlfriend and ate her. The cops allegedly found him screaming in the middle of the street with no memory of anything that had happened, just bits of her flesh in his stomach. He won't be getting out of prison.

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Previously: Lil Boosie Is Reportedly Out Of Prison
Lil Boosie Before The Bid
Lil Boosie Talks To XXL For His First Interview… Before His Press Conference
34 Hip-Hop Songs That Shout Out “Free Boosie”
10 Hip-Hop Songs That Shout Out “Free Remy Ma”