It doesn’t take much to get caught up in the mix. When a high-profile artist comes from a lifestyle of actual street activity or the glamorization of it, sometimes that can lead to legal issues and being targeted by the police. Unfortunately, many of rap’s most popular faces and names have done pretty lengthy bids in the can. Here’s a look at the rappers who’ve had long prison bids and how their run-ins with the law occurred.

There are a good amount of artists who have done their time but have since walked free. Take for example, JT of the City Girls. As the duo was rising in 2018, JT was sentenced to two years in prison for scamming and spent the latter half of her bid at a halfway house. Before 42 Dugg was dropping bars in the booth, he spent some time behind them as well. Dugg spent over six years in the can from 2010 to 2017 for carjacking and firearm charges.

Some rappers got trapped and slammed with RICO laws as well. Bobby Shmurda and Rowdy Rebel famously got arrested together on a slew of charges, alongside their other GS9 affiliates in 2014. Bobby and Rowdy have regained their freedom over the last couple of years. A similar situation happened with 6ix9ine in 2018, who aired out everyone he could offer to reduce his sentence drastically as he was looped into the crimes of the Nine Trey Bloods gang. The coronavirus pandemic is actually what trimmed some time off his sentence.

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To celebrate their return to the real world, it’s in character for a first day out song to follow. Gucci Mane comes to mind in that respect. He did a bid in 2009, for violating his probation and then again in 2014, for being caught with two firearms as a felon. The list goes on.

There are dozens of other rappers that have served or are serving prison sentences. Check out the longest prison bids in hip-hop history.

See 47 of the Longest Prison Bids in Hip-Hop History

C-Murder, Max B, B.G. and more.

Meek Mill performs onstage as Druski hosts first-ever “Coulda Fest” Comedy and Music Festival at State Farm Arena on September 07, 2024 in Atlanta, Georgia.

Paras Griffin/Getty Images

Meek Mill

Incarcerated: Nov. 6, 2017
Released: April 25, 2018
Amount Of Time: 171 days
Charge: Probation violation
What Happened: Following a 2017 assault case at St. Louis airport and a reckless driving charge that same year in New York City, a Philadelphia judge ordered Meek to two-to-four years behind bars for violating the probation sentence he got for a 2009 case for weapons and drugs. Meek was handed time despite having the reckless driving charge dropped and making a deal on the assault charge, which would have been wiped clean from his record if he had gone six months without getting in trouble. The judge who sentenced Meek was the same judge who oversaw his original case in 2009, where he was sentenced to 10 years on probation. Five months after the controversial two-to-four-year sentencing, Meek was released from prison. In 2019, the Reform Alliance was birthed by founders Jay-Z, Meek Mill, Philadelphia 76ers’ co-owner Michael Rubin and more to combat the unjust criminal justice system.

DMX performs at Masters Of Ceremony 2019 at Barclays Center on June 28, 2019 in New York City.

Theo Wargo, Getty Images

DMX

Incarcerated: Dec. 16, 2010
Released: July 18, 2011
Amount Of Time: 214 days
Charge: Probation violation
What Happened: Another case of, “Which time was that?” DMX was no stranger to the pen, and his probation violation for a drug-related offense in 2010 after an arrest in Arizona was another feather in his cap.

Tupac Shakur at Club USA, 1994. New York.

Steve Eichner, Getty Images

Tupac

Incarcerated: Feb. 14, 1995
Released: Oct. 10, 1995
Amount Of Time: 239 days
Charge: Sexual Assault
What Happened: Tupac Shakur was actually cleared of the majority of the charges in this case, in which a woman claimed she was raped by him and a number of other men in a hotel room in 1993. However, he was sentenced to a year-and-a-half in prison for “unwanted touching of the buttocks,” the only charge that stuck.

Lil Wayne performs onstage at the UPROAR Hip Hop Festival at Los Angeles Memorial Coliseum on August 13, 2021 in Los Angeles, California.

Rich Fury, Getty Images

Lil Wayne

Incarcerated: March 8, 2010
Released: Nov. 4, 2010
Amount Of Time: 241 days
Charge: Attempted criminal possession of a weapon
What Happened: In 2007, Lil Wayne got busted with a gun on his tour bus after a show in New York City. Two years later, he pleaded guilty to attempted criminal possession of a weapon for the incident and was required to serve a year in prison. He was sent to Rikers Island in 2010 to do the time, which ended up being a total of eight months.

Cassidy attends Drakes Till Death Do Us Part rap battle on October 30, 2021 in Long Beach, California.

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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.

Lil Kim attends the BET Awards 2021 at Microsoft Theater on June 27, 2021 in Los Angeles, California.

Paras Griffin, Getty Images

Lil’ Kim

Incarcerated: Sept. 19, 2005
Released: July 3, 2006
Amount Of Time: 287 days
Charge: Perjury and conspiracy
What Happened: A shooting outside the Hot 97 radio station in New York City in 2001 didn’t necessarily involve Lil’ Kim, but her lying to a grand jury about the incident afterward is what got her caught up. Video surveillance uncovered the truth, and there wasn’t much else Kim could do about it. She went to jail in 2005 for the crime.

T.I. performs onstage at Richard Mille after dark at Wayne & Cynthia Boichs Art Basel Party in partnership with Jetcraft on December 03, 2021 in Miami, Florida.

Alexander Tamargo, Getty Images

T.I.

Incarcerated: May 26, 2009
Released: March 26, 2010
Amount Of Time: 304 days
Charge: Federal weapons charges
What Happened: T.I. was facing 10 years on federal weapons possession charges, but a plea deal with prosecutors kept the rapper 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 shave off those nine years. T.I. was initially arrested on Oct. 13, 2007, by federal agents after he had a bodyguard buy machine guns and silencers for him.

Tory Lanez mugshot.

California Department of Corrections

Tory Lanez

Released: Still ongoing
Amount Of Time: Two years and counting
Charges: Assault with a semiautomatic firearm, carrying a loaded, unregistered firearm in a vehicle and discharging a firearm in a grossly negligent manner to cause bodily injury.
What Happened: On July 12, 2020, Tory Lanez was riding in an SUV in Los Angeles with Megan Thee Stallion and Megan’s former friend Nicole Harris when an argument took place, resulting in a shooting. Megan later identified Tory as the person who shot her in the back of her feet. Tory was charged with one felony count of assault with a semiautomatic firearm, carrying a loaded, unregistered firearm in a vehicle and discharging a firearm in a grossly negligent manner to cause bodily injury. He pleaded not guilty to the charges in November of 2020. Tory initially faced up to 22 years and eight months in prison, but was sentenced to eight years on Aug. 8, 2023.

Rapper Young Buck of G-Unit performs at the 10th annual Wine Amplified festival at the Las Vegas Village on October 10, 2015 in Las Vegas, Nevada.

David Becker, WireImage/Getty Images

Young Buck

Incarcerated: Aug. 13, 2012
Released: Oct. 1, 2013
Amount Of Time: 414 days
Charge: Weapon possession by a convicted felon
What Happened: Back in 2004, Young Buck was charged and convicted of stabbing a man at the Vibe Awards, putting the rapper in a position to no longer carry a gun or ammunition. In 2010, Buck’s home in Nashville was raided and as a result, police found a .40 caliber Glock 22 and ammo. The raid also revealed that he had a $300,000 tax debt. Since he was caught with possession of a weapon, Buck was sentenced to 18 months in prison.

JT of City Girls attends the BET Awards 2021 at Microsoft Theater on June 27, 2021 in Los Angeles, California.

Paras Griffin, Getty Images

JT

Incarcerated: June 29, 2018
Released: Oct. 8, 2019
Amount Of Time: 466 days
Charge: Felony identity theft
What Happened: The City Girls’ career took a bit of a hit in 2018, when JT was sentenced to two years in prison for scamming. She apparently used the credit cards of three different people between 2016 and 2017, and spent more than $1,000 of the stolen money. After her attorney in court name-dropped Drake and other artists who cosigned JT, she was able to finish the City Girls’ debut album promo before turning herself in. JT spent the latter half of her sentence at a halfway house. In 2019, she became a free woman after doing a little over a year for her crimes.

Rapper Tekashi 6ix9ine performs during the MiamiBash 2021 at FTX Arena on December 17, 2021 in Miami, Florida.

John Parra, Getty Images

6ix9ine

Incarcerated: Nov. 18, 2018
Released: April 2, 2020
Amount Of Time: 501 days
Charge: Federal racketeering and firearms charges
What Happened: 6ix9ine was arrested for RICO and firearms charges in late 2018, as a result of his affiliation and actions alongside the Nine Trey Gangster Bloods. The rapper accepted a plea deal that would lower his time in exchange for testifying against members of the gang. For his cooperation, 6ix9ine was sentenced to two years in prison and five years of supervised release, including the time he had already served. Once the COVID-19 pandemic sparked up, 6ix9ine was released on house arrest due to the health concerns surrounding his asthma. He was ultimately free on supervised release in 2020.

Tony Yayo attends the Starz Power The Fifth Season NYC Red Carpet Premiere Event & After Party on June 28, 2018 in New York City.

Jamie McCarthy, Getty Images

Tony Yayo

Incarcerated: Jan. 1, 2003
Released: May 25, 2004
Amount Of Time: 508 days, minus Jan. 8, 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, Tony Yayo went into the can in 2002, after cops found a gun in a car with 50 Cent, Lloyd Banks and Yayo. The other two got off scot-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.

Icewear Vezzo attends the BET Awards Radio Broadcast Center at Microsoft Theater on June 22, 2019 in Los Angeles, California.

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Icewear Vezzo

Incarcerated: 2017
Released: 2018
Amount Of Time: About 552 days
Charge: Gun possession by a felon
What Happened: In the fall of 2015, police pulled up on Icewear Vezzo and his associates at a gas station in Detroit. Upon rolling up, they spotted Vezzo take a Glock from out under his shirt and pass it to someone else. As a former felon, he was prohibited from carrying a firearm. In 2017, he was convicted of the felony gun charge and did 20 months for the violation. He was released in 2018.

Kodak Black performs on stage during Rolling Loud at Hard Rock Stadium on July 24, 2021 in Miami Gardens, Florida.

Rich Fury, Getty Images

Kodak Black

Incarcerated: May 11, 2019
Released: Jan. 19, 2021
Amount Of Time: 611 days
Charge: State and federal weapons charges
What Happened: Weeks after being arrested for weapons and drugs charges at the U.S. border, Kodak Black was roped again on state and federal firearms charges ahead of a Rolling Loud performance in May of 2019. He later confessed that he lied on background checks while buying guns on two different instances. Both guns were later discovered at crime scenes with one having Black’s fingerprints on it in an incident where it was allegedly used to fire at another artist. Yak was sentenced to nearly four years in prison, until former President Trump pardoned him in early 2021.

Ja Rule attends the Monster Energy $50K Charity Challenge Celebrity Basketball Game at UCLAs Pauley Pavilion on July 08, 2019 in Westwood, California.

Allen Berezovsky, Getty Images

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 for attempted weapons possession in 2007, on the same night as Lil Wayne (during separate incidents). With his many priors, Ja didn’t get off as easy as Weezy F. Baby did. While locked up beginning in 2011, Ja also got hit with 28 months for tax evasion, but the judge allowed that to be served concurrently with his gun charges.

Lil Baby attends the BET Awards 2021 at Microsoft Theater on June 27, 2021 in Los Angeles, California.

Paras Griffin, Getty Images

Lil Baby

Incarcerated: July 1, 2014
Released: July 1, 2016
Amount Of Time: 730 days
Charge: Probation violation
What Happened: Prior to receiving a two-year prison bid, Lil Baby was arrested multiple times on drug charges that stemmed from possession of marijuana and intent to sell. After one of his shorter sentences, where he got extra time for fighting a white prisoner over racist comments made, the rapper was arrested again in 2014, for violating his probation, officially sending him away for 730 days. Upon his release, Lil Baby launched his rap career.

Rapper Beanie Sigel attends the premiere of A Holiday Chance at TCL Chinese 6 Theatres on November 23, 2021 in Hollywood, California.

Paul Archuleta, Getty Images

Beanie Sigel

Incarcerated: Aug. 12, 2012
Released: Aug. 14, 2014
Amount Of Time: 732 days
Charge: Failure to file tax returns and illegal possession of prescription drugs
What Happened: Beanie Sigel was charged with three counts of failing to file tax returns on income of over $1 million between 2003–2005 in 2010, resulting in a 25-month prison sentence. In August of 2012, two weeks before he had to turn himself in to begin the bid, Sigel was arrested on drug, weapons and conspiracy charges after being pulled over by police. He began to serve time for his failure to file tax returns in the following month and was hit with an additional six to 23 months in county jail for illegal possession of prescription drugs. The time would be served concurrently with his prior sentence. In the summer of 2014, the rapper was released under the conditions that the remainder of his sentence be served in a halfway house.

Fetty Wap attends the Abyss by Abby show with preformance by Fetty Wap at Paraiso South Beach tent on July 14th, 2022 in Miami Beach, Florida.

Manny Hernandez/Getty Images

Fetty Wap

Incarcerated: Aug. 8, 2022
Released: Still ongoing
Amount Of Time: Two years and counting
Charges: Distributing more than 100 kilograms of cocaine, heroin, fentanyl and crack cocaine
What Happened: Fetty Wap was arrested on Oct. 29, 2021 after being accused by the FBI of distributing over 100 kilos of heroin, fentanyl, cocaine and crack cocaine alongside five others in the New York area and New Jersey. He was released on a $500,000 bond, but his bond was revoked and the rapper was later arrested for allegedly threatening to kill someone and waving a gun during a FaceTime call. Fetty’s attorney attempted to reduce his sentence, explaining that Fetty resorted to selling drugs due to the COVID-19 pandemic and requesting a five-year prison sentence. He was hit with six years after pleading guilty to the federal drug charges.

Tee Grizzley attends VaynerSports x ONE37pm Emerging Kings Party on February 01, 2019 in Atlanta, Georgia.

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Tee Grizzley

Incarcerated: July 1, 2014
Released: Oct. 18, 2016
Amount Of Time: 840 days
Charge: Theft by unlawful taking or disposition and two counts of second-degree home invasion
What Happened: Tee Grizzley was a student at Michigan State University when he went on a robbing spree with one of his associates. According to the police discovery after the fact, they stole at least $10,000 in cash and $10,000 worth of electronics in 2014. Tee and his accomplice were arrested but released as the police continued to gather evidence. In the meantime, Tee fled to Kentucky, where a smash and grab plan failed in 2015. He was arrested and sentenced to nine months for that crime. During that time, he was also sentenced to 18 months to 15 years for the 2014 university robberies. Tee Grizzley ended up serving over two years for his crimes.

Rapper Ol Dirty Bastard (aka. ODB & Dirt McGirt) attends a news conference to announce his signing with Roc-A-Fella Records at the Rihga Royal Hotel May 1, 2003 in New York City. The controversial rapper was released from prison earlier today after being incarcerated for over two years.

Scott Gries, Getty Images

Ol’ Dirty Bastard

Incarcerated: Nov. 28, 2000
Released: April 7, 2003
Amount Of Time: 860 days
Charge: Narcotics possession, traffic violations, fleeing rehab, becoming a fugitive and more
What Happened: ODB kind of went off the rails towards the end of the 1990s, with Wu-Tang Clan’s most eccentric member being arrested a series of times in just over a year. The initial charge that put him behind bars stemmed from a traffic bust in 1999, in which cops found crack cocaine and marijuana on him. 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 in 2000. A few months after, he was kicked out of rehab, then sentenced again to more rehab. Subsequently, 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 arrested again a week later at a McDonald’s. He was finally sentenced to two to four years in prison for the variety of offenses.

Rapper Drakeo the Ruler performs onstage during Rolling Loud at NOS Events Center on December 12, 2021 in San Bernardino, California.

Scott Dudelson, Getty Images

Drakeo The Ruler

Incarcerated: March of 2018
Released: Nov. 4, 2020
Amount Of Time: About 979 days
Charge: First-degree murder and attempted murder
What Happened: Drakeo The Ruler was charged with first-degree murder, attempted murder and conspiracy to commit murder as a result of a 2016 shooting, in which one person was killed and two were injured. Though the rapper wasn’t physically at the crime, police tagged him to the incident on the idea that he provided firearms and the getaway vehicle. In 2019, Drakeo was acquitted, but the district attorney decided to refile charges of criminal gang conspiracy and firing from a vehicle against him, resulting in a hung jury. After three years, the rhymer was released on a plea deal in 2020, after pleading guilty to shooting from a motor vehicle with a gang enhancement. While this meant acknowledging in a court of law that the Stinc Team the rapper was part of was a gang, Drakeo claimed he was never part of a gang and proclaimed his innocence.

Gucci Mane arrives at the Gucci show during Milan Fashion Week Spring/Summer 2020 on September 22, 2019 in Milan, Italy.

Vittorio Zunino Celotto, Getty Images

Gucci Mane

Incarcerated: Sept. 14, 2013
Released: May 26, 2016
Amount Of Time: 985 days
Charge: Possession of a firearm by a convicted felon
What Happened: In the fall of 2013, Gucci Mane was taken into custody for behaving erratically. A friend called and upon the police showing up, Gucci Mane was charged with carrying a firearm, possession of marijuana and disorderly conduct. As a felon who was caught with a gun, Gucci was in big trouble but agreed to a plea deal that still landed him years in prison.

In this handout photo provided by the Browards Sheriffs Office, rapper YNW Melly, real name Jamell Demons, is seen in a police booking photo after being charged with two counts of murder in the first degree February 13, 2019 in Ft. Lauderdale, Florida. Demons allegedly conspired with Cortlen Henry to fatally shot two other Florida based rappers, Christopher Thomas Jr and Anthony Williams, October 26.

Handout, Getty Images

YNW Melly

Incarcerated: Feb. 13, 2019
Released: Still ongoing
Amount Of Time: Six years and counting
Charge: First-degree murder
What Happened: Days before Halloween of 2018, YNW Melly’s childhood friends YNW Sakchaser and YNW Juvy were pronounced dead in what appeared to be a drive-by shooting. Melly’s friend and fellow rapper YNW Bortlen was the driver of the vehicle the bodies were found in, and was arrested in February of 2019, for being an accessory to murder. A day later, YNW Melly was arrested for the murders of Sakchaser and Juvy. Forensic evidence confirmed that Melly killed the two men and staged the scene to appear as if it was a drive-by alongside Bortlen. After additionally being linked to the fatal shooting of a deputy, Melly is being held without bond in a Florida jail. Melly stood trial, which ended in a hung jury in July of 2023. His retrial date is set for Oct. 10, 2025.

Rapper Fat Trel attends MMGs Weekend The #BIGGEST Pool Party on July 3, 2016 in Fayetteville, Georgia.

Prince Williams, Getty Images

Fat Trel

Incarcerated: July 8, 2018
Released: Oct. 15, 2021
Amount Of Time: 1,195 days
Charge: Illegal possession of a firearm by a previously convicted felon
What Happened: Due to traffic violations, Fat Trel was arrested for possession of a firearm and ammunition in the summer of 2018. Upon that moment, officers realized that he had a suspended license and no ID, so they searched the vehicle and found a “ghost gun.” Trel pleaded guilty for illegal possession of the weapon in 2020, and faced 10 years. In September of that year, his sentence was squeezed down to two years and six months, along with three years of supervised release. He got out in October of 2021, due to time served, though he’s since found himself back behind bars.

Rapper Prodigy from the group Mobb Deep make? an appearance at MTV studios for a taping of MTV 2 Presents Sucker Free Week on April 6, 2006 in New York City.

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Prodigy

Incarcerated: Oct. 8, 2007
Released: March 7, 2011
Amount Of Time: 1,246 days
Charge: Felony gun possession
What Happened: He already had gun charges in the past from 2003. An illegal u-turn on the highway caused a patrolman to search his vehicle and find another gun as well in 2006. He kept busy while locked up, though, writing a book on his life’s experiences.

Rapper 03 Greedo attends the Trap House Clothing & Laced South Bay Presents TRAP ALL STAR FEST at The Belasco Theater on February 15, 2018 in Los Angeles, California.

Unique Nicole, Getty Images

03 Greedo

Incarcerated: June 28, 2018
Released: Jan. 12, 2023
Amount Of Time: 1,659 days
Charge: Drug trafficking and possession of a firearm
What Happened: 03 Greedo got roped in the summer of 2016, on drug trafficking and possession of a firearm charges. The police reportedly opened his trunk after smelling weed and located four pounds of methamphetamine and two stolen guns. 03 Greedo took a plea deal in 2018, and was sentenced to two decades in prison, with the potential to be released in five years with good behavior. He was denied parole in 2020, but was officially released on Jan. 12, 2023 after more than four years behind bars.

Rapper Pimp-C of the rap group UGK during the video shoot for the lead off street anthem Pourin Up from Pimp-Cs highly anticipated solo album Pimpalation on April 3, 2006 in Houston, Texas.

Bill Olive, Getty Images

Pimp C

Incarcerated: Jan. 2002
Released: Dec. 30, 2005
Amount Of Time: 1,445 days
Charge: Probation violation related to an aggravated assault charge
What Happened: Pimp C got into an argument at a mall with a woman in 2000, then he apparently flashed a gun, and was arrested. When he fell behind on community service, a judge sent him to jail in 2002, much to the anger and protest of the hip-hop community who, led by Bun B, started the Free Pimp C campaign.

Boosie Badazz attends the BET Hip Hop Awards 2019 at Cobb Energy Center on October 05, 2019 in Atlanta, Georgia.

Carmen Mandato, Getty Images

Boosie BadAzz

Incarcerated: Nov. 9, 2009
Released: March 5, 2014
Amount Of Time: 1,577 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. The judge then doubled the sentence 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 after being accused of the 2009 killing of another local rapper. He stared down the death penalty and won the case, and celebrated with his release in 2014 after five years behind bars.

Tay-K The Race music video

Buffet Boys via YouTube

Tay-K

Incarcerated: June 30, 2017
Released: Still ongoing
Amount Of Time: Eight years and counting
Charge: Murder and aggravated robbery
What Happened: Tay-K was arrested and charged with a group of people in a botched robbery in July of 2016, that left one dead. While under house arrest, Tay-K broke off his ankle monitor and did the race, resulting in the inception of the multiplatinum-selling song. After he was apprehended, he was charged with another murder as police believed that he killed a photographer in an attempt to steal his photography equipment. In 2019, the rapper was sentenced to 55 years for the murder charge, 30 years for one of the aggravated robbery counts, and two 13-year sentences for the remaining two counts of aggravated robbery. They will all be served concurrently. Tay-K was also fined $21,000 for a combination of his crimes.

In February of 2024, video footage began circulating online of Tay-K at a court hearing, rejecting a plea deal in his second murder case. In April of 2025, he was found guilty at trial and sentenced to 80 years. The sentence will run concurrently with his first sentence.

Rapper 42 Dugg attends the Boston Celtics v Atlanta Hawks game at State Farm Arena on November 17, 2021 in Atlanta, Georgia.

Paras Griffin, Getty Images

42 Dugg

Incarcerated: October of 2010; May 5, 2022
Released: 2017; Oct. 16, 2023
Amount Of Time: About 2,719 days
Charge: Carjacking and gun possession
What Happened: Back in 2010, a 15-year-old 42 Dugg got arrested for carjacking and felony firearms possession. He was sentenced to four years in the can until a physical altercation with another inmate led to him being placed in solitary confinement and getting an additional two years for the fight. While in solitary, he began writing raps in his notebook and took the art seriously upon his release in 2017. In April of 2023, Dugg was sentenced to a year in prison for failure to surrender for service of sentence. This charge stems from a November of 2020 arrest for a federal gun probe. Dugg was supposed to begin his sentence on April 12, 2022, but failed to appear. He was arrested by Federal Agents in May of 2022 after landing in Detroit on a private plane. The Michigan-bred rapper was released from the United States Penitentiary Atlanta on Oct. 16, 2023.

Slick Rick attends the 2018 Angel Ball at Cipriani, Wall Street on October 22, 2018 in New York City.

Roy Rochlin, Getty Images

Slick Rick

Incarcerated: June 24, 1991
Released: June 4, 1997
Amount Of Time: 2,172 days
Charge: Attempted murder and weapons charges
What Happened: Just as his career was picking up, Slick Rick got busted for shooting his cousin, who was also a bodyguard, in 1991, for attempting to extort the rapper. Unfortunately, Rick also shot an innocent person standing nearby, and a police chase resulted in the artist picking up attempted murder charges. He served five years in prison.

Mystikal attends the 2013 BMI R&B/Hip-Hop Awards at Hammerstein Ballroom on August 22, 2013 in New York City.

Neilson Barnard, Getty Images

Mystikal

Incarcerated: Jan. 15, 2004; July 21, 2022
Released: Jan. 14, 2010; still in custody
Amount Of Time: Two years and counting
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 hairstylist turned really ugly. In, 2002, he was charged with aggravated rape and extortion after police arrested him and two bodyguards for threatening that his former hairstylist would need to perform oral sex of them or else Mystikal would turn her in to police for allegedly cashing $80,000 worth of unauthorized checks from the rapper’s bank account. The MC sat very firmly behind bars for the better part of a decade after being sentenced to a six-year prison term for sexual battery in 2004.

On July 31, 2022, Mystikal was arrested on charges of rape and false imprisonment after being accused of brutally raping and assaulting a woman, who was said to be in a long-time relationship with the rapper, at his Prairieville, La. home. In September of 2022, he was indicted by a grand jury for first-degree rape in connection with the incident, and he reportedly faces life in prison.

Rowdy Rebel attends Power 105.1s Powerhouse 2021 at Prudential Center on November 21, 2021 in Newark, New Jersey.

Johnny Nunez, Getty Images

Rowdy Rebel

Incarcerated: Dec. 17, 2014
Released: Dec. 15, 2020
Amount Of Time: 2,198 days
Charge: Conspiracy and weapons charges
What Happened: Rowdy Rebel was arrested alongside Bobby Shmurda and other members of the Brooklyn-bred gang GS9 in 2014. He was hit with a slew of charges including attempted murder and criminal possession of a weapon. On conspiracy and weapons charges, Rowdy was sentenced to 12 years in the can, until his right-hand Bobby, who was only sentenced to five years at the time, accepted a seven-year plea deal that would lessen Rowdy’s time. Rowdy Rebel walked free in December of 2020.

Jay-Zs 40/40 Club 18th Anniversary celebration at 40/40 Club on August 28, 2021 in New York City.

Johnny Nunez, WireImage

Bobby Shmurda

Incarcerated: Dec. 17, 2014
Released: Feb. 23, 2021
Amount Of Time: 2,260 days
Charge: Conspiracy, reckless endangerment and weapons charges
What Happened: Right as his multiplatinum hit “Hot Nigga” was blowing up, Bobby Shmurda was arrested alongside other members of his GS9 gang on multiple charges of conspiracy, murder, drugs and weapons possession in Dec. 17, 2014 at Quad Studios. After receiving a seven-year sentence, with additional charges for smuggling in contraband, Bobby served most of his time but was denied release in the fall of 2020. However in early 2021, he ended up walking free at the end of his maximum expiration, not long after Rowdy Rebel came home.

Remy Ma attends Jay-Zs 40/40 Club 18th Anniversary at 40 / 40 Club on August 28, 2021 in New York City.

Dimitrios Kambouris, Getty Images

Remy Ma

Incarcerated: March 27, 2008
Released: Aug. 1, 2014
Amount Of Time: 2,318 days
Charge: Assault, illegal weapon possession and attempted coercion
What Happened: In 2008, Remy Ma was convicted of assault, illegal weapon possession and attempted coercion after being accused of shooting a friend during an argument after $3,000 came up missing from her purse in 2007. Although Remy claimed the incident was an accident, she was sentenced to eight years behind bars. Remy served six of her eight-year sentence and was released from Bedford Hills Correctional Facility for Women on Aug. 1, 2014.

Mysonne attends Verzuz: The Lox Vs Dipset at Madison Square Garden on August 03, 2021 in New York City.

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Mysonne

Incarcerated: July 31, 1999
Released: July 5, 2006
Amount Of Time: 2,531 days
Charge: Armed Robbery
What Happened: Just as he was about to drop his debut studio album in 1999, after a string of highly successful mixtapes, Mysonne felt the hammer fall with two convictions. He was charged with armed robbery stemming from two separate cab driver robberies in 1998, both for which he claimed his innocence. Fourteen years came down from the judge, and even though he only ended up serving seven, he never really recovered career-wise. He was released in 2006.

Flesh-n-Bone of Bone Thugs-n-Harmony performs during the TLCs Celebration of Crazy Sexy Cool tour at FPL Solar Amphitheater at Bayfront Park on September 27, 2021 in Miami, Florida.

Johnny Louis, Getty Images

Flesh-n-Bone

Incarcerated: Sept. 22, 2000
Released: July 13, 2008
Amount Of Time: 2,851 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 in 1999. The judge was able to show some mercy, pointing out the rapper’s sadly extensive history of being abused as a child, but still sent him away for 12 years to straighten out beginning in 2000.

Shyne attends Jay-Zs 40/40 Club 18th Anniversary at 40 / 40 Club on August 28, 2021 in New York City.

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Shyne

Incarcerated: June 1, 2001
Released: Oct. 6, 2009
Amount Of Time: 3,049 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 in 1999, which resulted in Diddy and then-girlfriend Jennifer Lopez fleeing in a car before being pulled over. The rapper admitted to firing a gun in self-defense at Club New York. Shyne claimed another gunman’s bullets injured two victims. Once he was released from prison in 2009, Shyne was deported and sent back to his native Belize.

Turk attends BMIs 2013 R&B/Hip-Hop Awards at The Manhattan Center on August 22, 2013 in New York City.

Taylor Hill, Getty Images/FilmMagic

Turk

Incarcerated: April 1, 2004
Released: Oct. 12, 2012
Amount Of Time: 3,116 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 shooting Memphis police officers in 2004. Turk was charged with first-degree attempted murder for allegedly shooting two Memphis cops during a raid in an apartment he was found in. The attempted murder rap that got him a sentence of 14 years, of which he served almost nine.

Rapper BG attends the 4th Annual VH1 Hip Hop Honors ceremony at the Hammerstein Ballroom on October 4, 2007 in New York City.

Bryan Bedder, Getty Images

B.G.

Incarcerated: July 18, 2012
Released: Sept. 5, 2023
Amount Of Time: 3,701 days
Charge: Felony gun possession and witness tampering
What Happened: A traffic stop in 2009 led to cops finding three guns—two of which, as well as the car, were stolen—and as B.G. 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 B.G.’s request, they tacked on tampering to the charge. The former Cash Money artist was sentenced to 14 years but only served 11 years. B.G. was released from prison on Sept. 5, 2023.

G. Dep Special Delivery music video

Bad Boy Entertainment via YouTube

G. Dep

Incarcerated: May 8, 2012
Released: April 4, 2024
Amount Of Time: 4,349 days
Charge: Murder
What Happened: Former Bad Boy Records signee G. Dep was found guilty of the 1993 murder of a Queens-bred man named John Henkel. As the story goes, back in 2010, G. Dep walked into the New York Police Department’s 25th Precinct in Harlem and made the confession that he killed the man in a botched robbery attempt in 1993. On trial, a jury of 12 officially linked him to the murder and the rapper was incarcerated in 2012. G-Dep was released on April 4, 2024 after serving 13 years for a murder he committed over a decade ago.

Bump J Good 2 Be Home music video

Bump J via YouTube

Bump J

Incarcerated: Nov. 13, 2008
Released: April 12, 2017
Amount Of Time: 3,702 days
Charge: Bank Robbery and weapons charges
What Happened: Bump J and another man walked into a Chicago bank and emptied it of $100,000 in 2007, before going out on the run. The Chicago rapper would eventually get arrested during a traffic stop after in 2008, when police caught up with him. Bump J entered a plea deal, taking seven years for the heist. He was released in 2017.

Chi-Ali attends TrillerVerz Featuring Super Cat, KRS 1 & Big Daddy Kane at Barclays Center on October 17, 2021 in New York City.

Johnny Nunez, Getty Images

Chi-Ali

Incarcerated: March 5, 2001
Released: Aug. 28, 2012
Amount Of Time: 4,102 days
Charge: Manslaughter
What Happened: In January of 2000, Native Tongues rhymer Chi-Ali was involved in the death of his brother-in-law after an argument ended in the man being shot and killed. Chi-Ali went out on the run, leading authorities on more than a year-long chase. He was captured in March of 2001, when he was finally charged with the killing. Chi-Ali ended up on America’s Most Wanted during that time, and was hit with 14 years for the crime.

First Video of Max B from Prison in 10+ years

Max B via YouTube

Max B

Incarcerated: Sept. 3, 2009
Released: Still ongoing
Amount Of Time: Fifteen years and counting
Charge: Convicted of conspiracy to armed robbery, kidnapping, aggravated assault and murder
What Happened: A hotel robbery gone bad, according to the Feds. Max B wasn’t even at the scene of the crime, but New Jersey courts ruled that he was part of a conspiracy that resulted in the shooting death of a man in 2006. Biggaveli’s on-again-off-again girlfriend and another acquaintance shot the man while attempting to rob his friend. He may not have been there, but Max B received a 75-year prison sentence after being pinned in the conspiracy. However, after going back to the drawing board with his case, Max’s charges have since been reduced to manslaughter and his sentence shortened to just 12 years. He is expected to be released in November of 2025.

When the Levees Broke: A Requiem in Four Acts New Orleans Premiere – Arrivals: C-Murder with girlfriend and Kernel.

Skip Bolen, Getty Images

C-Murder

Incarcerated: Aug. 14, 2009
Released: Still ongoing
Amount Of Time: Fifteen years and counting
Charge: Second degree murder
What Happened: He’s actually served longer than that, but a re-trial following his initial conviction in September of 2003 placed him on house arrest until the second conviction in 2009. In January of 2002, a 16-year-old at a nightclub was caught up in an altercation outside the venue, where 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.

Choppin Game w/ the OG -Mr. Marcelo & G Da $treet Analyst Ep.15 w/ NOLA Legend McKinley “Mac” Phipps

Boom Multimedia Podcast Network via YouTube

Mac Phipps

Incarcerated: Sept. 21, 2001
Released: June 22, 2021
Amount Of Time: 7,214 days
Charge: Manslaughter
What Happened: In February of 2000, No Limit rapper Mac Phipps was slated to perform at a Louisiana club before a fight broke out and ended with a gun shot that killed a 19-year-old man. Phipps was charged with murder, though it was reduced to a 30 years to life manslaughter sentence in September of the following year. A security guard who was present at the incident later confessed to the shooting, but the police still decided to pursue charges against Phipps, making this a high-profile case of wrongful imprisonment. After spending nearly 20 years behind bars, Mac was granted clemency and walked free in the summer of 2021.

Big Lurch Presents: Lurchology Part 2. – End Result’s / Black Republican Party

Antron Singleton Jr via YouTube

Big Lurch

Incarcerated: April 10, 2002
Released: Still ongoing
Amount Of Time: 8,199 days and counting
Charge: Murder, torture and aggravated mayhem
What Happened: It’s like a walking advertisement against PCP. Bay Area rapper Big Lurch was high on PCP when he attacked a woman who was dating a friend of his and ate her in 2002. During the attack, he broke the woman’s neck and jaw, stabbed her, removed her lung and fractured an eye socket. The cops allegedly found Lurch covered in blood and screaming in the middle of the street with no memory of anything that had happened. A medical examination of Lurch while in custody resulted in bits of the woman’s flesh being found in his stomach. He was sentenced to life in prison for the murder in 2003.

Read More: Longest Prison Bids in Hip-Hop History | https://www.xxlmag.com/26-of-the-longest-prison-bids-in-hip-hop-history/?utm_source=tsmclip&utm_medium=referral