10 Rappers Who Went To Jail At The Height Of Their Popularity
Maybach Music Group rapper Gunplay sure picked a baaaaaaad time to get into legal trouble. After putting in a ton of work behind the scenes and playing second fiddle to his close friend Rick Ross for years, the Miami rapper was finally on the verge of making a breakthrough after releasing his mixtape, 601 & Snort, last month. Although he was on the wrong end of a beef with 50 Cent at the 2012 BET Awards recently, the fight that took place put him front and center on the rap blogs and made him a rapper to watch for in the near future. Things were finally looking ups or him.
But now, it's all falling apart. Last week, Gunplay turned himself into police in Miami on an outstanding warrant stemming from old armed robbery and assault charges. A video of him assaulting a man thought to be his accountant also hit the 'net and started making the rounds. And, it was reported that Gunplay could be stuck in jail for a long, long time unless his lawyers can make some magic happen. In the course of a week, Gunplay went from hip-hop's next big thing to a guy struggling just to stay out of jail.
He's not the first rapper to endure this kind of battle, though. In the past, there have been a number of rappers who have faced legal troubles just as they were starting to shine their brightest. So, in light of Gunplay's recent arrest, we put together a list of 10 Rappers Who Went To Jail At The Height Of Their Popularity. Some of them recovered; others weren't so lucky. But, they all had their careers altered by a jail sentence.
But now, it's all falling apart. Last week, Gunplay turned himself into police in Miami on an outstanding warrant stemming from old armed robbery and assault charges. A video of him assaulting a man thought to be his accountant also hit the 'net and started making the rounds. And, it was reported that Gunplay could be stuck in jail for a long, long time unless his lawyers can make some magic happen. In the course of a week, Gunplay went from hip-hop's next big thing to a guy struggling just to stay out of jail.
He's not the first rapper to endure this kind of battle, though. In the past, there have been a number of rappers who have faced legal troubles just as they were starting to shine their brightest. So, in light of Gunplay's recent arrest, we put together a list of 10 Rappers Who Went To Jail At The Height Of Their Popularity. Some of them recovered; others weren't so lucky. But, they all had their careers altered by a jail sentence.
The Rapper: Lil Wayne
Why He Went To Jail: In October 2009, two years after he was found to be in possession of a gun illegally in New York City, Wayne pleaded guilty to attempted criminal possession of a weapon. He was sentenced to serve a one-year jail sentence that began in March 2010.
How It Affected His Career: Since being released from jail in late 2010, Wayne has released a slew of projects, including Tha Carter IV. He's also made plenty of headlines for skateboardin g. But, there's no denying that Wayne isn't nearly as popular today as he was back before he went to jail. And, it's hard to see him ever regaining the crazy buzz he had before he went behind bars.
Why He Went To Jail: In October 2009, two years after he was found to be in possession of a gun illegally in New York City, Wayne pleaded guilty to attempted criminal possession of a weapon. He was sentenced to serve a one-year jail sentence that began in March 2010.
How It Affected His Career: Since being released from jail in late 2010, Wayne has released a slew of projects, including Tha Carter IV. He's also made plenty of headlines for skateboardin
The Rapper: T.I.
Why He Went To Jail: Which time? Since he started rapping, Tip's career has been sidelined several times while he's served time. Most notably, he was sentenced to serve a year and a day in federal prison in March 2009 on federal weapons charges.
How It Affected His Career: T.I.'s last three albums—2008's Paper Trail, 2010's No Mercy, and his latest project, Trouble Man—have all been either completed while T.I. was awaiting sentencing or recorded shortly after he got out of jail. As a result, he's never really been able to maintain a consistent buzz. So, now that he's finally free and clear, we hope he's able to pick up where he left off before all the legal troubles started. But, it's not going to be easy.
Why He Went To Jail: Which time? Since he started rapping, Tip's career has been sidelined several times while he's served time. Most notably, he was sentenced to serve a year and a day in federal prison in March 2009 on federal weapons charges.
How It Affected His Career: T.I.'s last three albums—2008's Paper Trail, 2010's No Mercy, and his latest project, Trouble Man—have all been either completed while T.I. was awaiting sentencing or recorded shortly after he got out of jail. As a result, he's never really been able to maintain a consistent buzz. So, now that he's finally free and clear, we hope he's able to pick up where he left off before all the legal troubles started. But, it's not going to be easy.
The Rapper: Max B
Why He Went To Jail: In June 2009, he was found guilty of murder conspiracy and robbery charges stemming from a 2007 incident that left a man dead in a New Jersey hotel robbery. He was sentenced to 75 years in prison.
How It Affected His Career: Just prior to being sentenced, Max B was enjoying a real moment thanks to the success of his Coke Wave mixtapes. But, his movement was obviously put to a halt once he went away. And, barring some sort of miracle, it doesn't sound like he'll ever get the chance to try and start it up again.
Why He Went To Jail: In June 2009, he was found guilty of murder conspiracy and robbery charges stemming from a 2007 incident that left a man dead in a New Jersey hotel robbery. He was sentenced to 75 years in prison.
How It Affected His Career: Just prior to being sentenced, Max B was enjoying a real moment thanks to the success of his Coke Wave mixtapes. But, his movement was obviously put to a halt once he went away. And, barring some sort of miracle, it doesn't sound like he'll ever get the chance to try and start it up again.
The Rapper: Gucci Mane
Why He Went To Jail: In 2005, he served a six-month jail sentence on aggravated assault charges stemming from the 2004 beating of a concert promoter. But, he was ordered to report back to prison in 2008 after he failed to complete community service hours as part of his probation from that crime. Subsequently , he was also arrested in November 2010 on a bunch of traffic-rela ted crimes and again in early 2011 on battery charges.
How It Affected His Career: Although all of his crimes helped propel his 2009 album, The State vs. Radric Davis, to the top of the U.S. Billboard 200 chart, they have also hindered his growth as an artist. It seems like every time he starts working on a project, he gets into trouble again and it delays the process. As a result, he's had trouble releasing projects with any sort of consistency.
Why He Went To Jail: In 2005, he served a six-month jail sentence on aggravated assault charges stemming from the 2004 beating of a concert promoter. But, he was ordered to report back to prison in 2008 after he failed to complete community service hours as part of his probation from that crime. Subsequently
How It Affected His Career: Although all of his crimes helped propel his 2009 album, The State vs. Radric Davis, to the top of the U.S. Billboard 200 chart, they have also hindered his growth as an artist. It seems like every time he starts working on a project, he gets into trouble again and it delays the process. As a result, he's had trouble releasing projects with any sort of consistency.
The Rapper: Remy Ma
Why She Went To Jail: The former Terror Squad MC began serving an eight-year sentence in March 2008 on a host of different charges stemming from the July 2007 shooting of Remy's former friend Makeda Barnes-Josep h.
How It Affected Her Career: When Remy went away, she was arguably the biggest female rapper on the scene. Now, with the emergence of Nicki Minaj and a bunch of other female MCs, it's unlikely that Remy will still have her spot when she gets out of jail in 2015. And, it's unfortunate, because her debut, There's Something About Remy, was promising.
Why She Went To Jail: The former Terror Squad MC began serving an eight-year sentence in March 2008 on a host of different charges stemming from the July 2007 shooting of Remy's former friend Makeda Barnes-Josep
How It Affected Her Career: When Remy went away, she was arguably the biggest female rapper on the scene. Now, with the emergence of Nicki Minaj and a bunch of other female MCs, it's unlikely that Remy will still have her spot when she gets out of jail in 2015. And, it's unfortunate, because her debut, There's Something About Remy, was promising.
The Rapper: Cassidy
Why He Went To Jail: After being involved in an April 2005 shooting, the Philadelphia rapper was sentenced to 11 to 23 months on involuntary manslaughter charges.
How It Affected His Career: Cassidy's sophomore album, I'm A Hustla, was released right in the middle of all his legal troubles. And, while it sold well, it quickly came and went and Cass never really regained the spark that he had once he served his time in jail. He did release one more major label album, B.A.R.S. The Barry Adrian Reese Story, but it didn't sell particularly well. As a result, Cassidy has spent the last few years trying to regain the buzz he had before all of his legal problems started.
Why He Went To Jail: After being involved in an April 2005 shooting, the Philadelphia rapper was sentenced to 11 to 23 months on involuntary manslaughter charges.
How It Affected His Career: Cassidy's sophomore album, I'm A Hustla, was released right in the middle of all his legal troubles. And, while it sold well, it quickly came and went and Cass never really regained the spark that he had once he served his time in jail. He did release one more major label album, B.A.R.S. The Barry Adrian Reese Story, but it didn't sell particularly well. As a result, Cassidy has spent the last few years trying to regain the buzz he had before all of his legal problems started.
The Rapper: Shyne
Why He Went To Jail: He was sentenced to ten years in jail in June 2001 for his role in the December 1999 Club New York shooting that involved Sean "Diddy" Combs and Jennifer Lopez.
How It Affected His Career: It obviously didn't help it. Once thought to be Bad Boy's next big superstar, Shyne released one project while he was in prison, 2004's Godfather Buried Alive. But, he's struggled to start his career up again ever since he was released from jail in late 2009.
Why He Went To Jail: He was sentenced to ten years in jail in June 2001 for his role in the December 1999 Club New York shooting that involved Sean "Diddy" Combs and Jennifer Lopez.
How It Affected His Career: It obviously didn't help it. Once thought to be Bad Boy's next big superstar, Shyne released one project while he was in prison, 2004's Godfather Buried Alive. But, he's struggled to start his career up again ever since he was released from jail in late 2009.
The Rapper: Slick Rick
Why He Went To Jail: He served a five-year jail sentence on attempted murder charges after he shot an innocent bystander and one of his bodyguards who had allegedly tried to have him shot in 1990.
How It Affected His Career: Prior to going to jail, the Ruler had been riding high off the success of his debut, 1988's The Great Adventures of Slick Rick. He did record another album, 1991's The Ruler's Back, before serving his time and also stashed away enough material for Def Jam to put out an album called Behind Bars in 1994 while he was still in jail. But, neither lived up to the classic status of his first project. He was also deported upon being released from jail and struggled to work in the U.S. for years before he was pardoned by New York Governor David Paterson in 2008.
Why He Went To Jail: He served a five-year jail sentence on attempted murder charges after he shot an innocent bystander and one of his bodyguards who had allegedly tried to have him shot in 1990.
How It Affected His Career: Prior to going to jail, the Ruler had been riding high off the success of his debut, 1988's The Great Adventures of Slick Rick. He did record another album, 1991's The Ruler's Back, before serving his time and also stashed away enough material for Def Jam to put out an album called Behind Bars in 1994 while he was still in jail. But, neither lived up to the classic status of his first project. He was also deported upon being released from jail and struggled to work in the U.S. for years before he was pardoned by New York Governor David Paterson in 2008.
The Rapper: Mysonne
Why He Went To Jail: In 1999, he was convicted on two armed robbery charges and sentenced to seven to 14 years in jail.
How It Affected His Career: At the time, he was getting ready to release his debut, Life Teaches and Reality Bites, on Def Jam. But, it was shelved after he went away. He was released from jail in 2006 and tried to jumpstart his rap career again. But, so far, he's had little success.
Why He Went To Jail: In 1999, he was convicted on two armed robbery charges and sentenced to seven to 14 years in jail.
How It Affected His Career: At the time, he was getting ready to release his debut, Life Teaches and Reality Bites, on Def Jam. But, it was shelved after he went away. He was released from jail in 2006 and tried to jumpstart his rap career again. But, so far, he's had little success.
The Rapper: 2Pac
Why He Went To Jail: After a woman accused 'Pac and several of his friends of sexually assaulting her in November 1993, he was sentenced to serve 1.5 to 4.5 years in prison.
How It Affected His Career: This is one of the few situations in which a jail sentence didn't really hurt a rapper. While he was incarcerated , 2Pac released Me Against the World and it went to the top of the Billboard charts. He also earned a recording contract with Death Row Records due to the fact that Suge Knight helped pay his way out of prison. He went on to release several successful albums with the label before his untimely death. Still, 'Pac was a rare case. And, as you can see from most of the other examples here, crime most definitely does not pay when you're a rapper.
Why He Went To Jail: After a woman accused 'Pac and several of his friends of sexually assaulting her in November 1993, he was sentenced to serve 1.5 to 4.5 years in prison.
How It Affected His Career: This is one of the few situations in which a jail sentence didn't really hurt a rapper. While he was incarcerated

