First things first: There’s no “good” time for a rapper to go to jail. No matter which way you slice it, jail/prison sucks—and we hate that so many rappers have been thrown behind bars over the years. But last week, Meek Mill got sentenced to three to six months in jail for issues surrounding his probation, just a few days after he announced the release date for his sophomore album, Dreams Worth More Than Money.
As a result, there’s a chance that he could be locked up when his album drops on September 9, which would obviously be a big blow to the MMG rapper’s career. But Meek isn’t the first rapper to end up in this predicament. Other MCs have gone away either right at the height of their popularity or right when they were gearing up to drop an album. In light of Meek’s situation, here are 10 rappers who went to jail at the worst time possible. The timing of their sentences couldn’t have been any worse.
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The Rapper: Shyne
When He Went To Jail: June 2001 (after he was involved in a shooting at a club in New York City in December 1999)
Why It Was The Worst Time Possible: Shyne’s career was literally just getting started when he caught his charge at the turn of the century. Had he not gone to prison, he very well could have gone on to have a long and successful career. But instead, he spent his prime years sitting behind bars wondering, “What if…?”Photo Credit: Getty Images
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The Rapper: Cassidy
When He Went To Jail: January 2006 (after he was involved in a murder that took place in Philadelphia in April 2005)
Why It Was The Worst Time Possible: Cassidy landed in hot water about a month before the release of his second album, I’m a Hustla. It hindered his ability to promote the project and eventually forced him to wait another two years before getting back on his rap grind. And he never really recovered after his hiatus.Photo Credit: Getty Images
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The Rapper: Max B
When He Went To Jail: January 2007 (after he masterminded a robbery attempt in New Jersey in September 2006)
Why It Was The Worst Time Possible: Max B was everywhere in 2006, 2007, and even 2008. He was arguably the hottest rapper in the streets at the time and there was a big buzz following him around. But unfortunately, everything that he put out during that time period was mixtape material, so he never really got to cash in on all of the success that he enjoyed. He missed out on so much tour money and never had the chance to release a proper debut album because of his jail sentence.Photo Credit: Getty Images
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The Rapper: Remy Ma
When She Went To Jail: March 2008 (after she shot one of her friends in New York City in July 2007)
Why It Was The Worst Time Possible: Thanks to the success of her 2005 songs “Whuteva” and “Conceited,” Remy’s debut album, There’s Something About Remy, was a success in 2006. But she never got to release a follow-up to that project because of her legal issues. There’s a chance that she could drop one once she gets out of prison this summer. But now that she’s been out of the game for so long, it’s won’t be easy for her to make a comeback.Photo Credit: Getty Images
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The Rapper: T.I.
When He Went To Jail: May 2009 (after he got busted trying to buy weapons from an undercover federal agent in October 2007)
Why It Was The Worst Time Possible: Although he had to record most of his 2008 album, Paper Trail, under house arrest, it still did really well for him. It featured “Whatever You Like,” one of his biggest songs to date. But whatever momentum he achieved by recording that album went out the window when Tip went to jail the following year, and he’s spent most of the last five years trying to get back into that space that he was in before he went away.Photo Credit: Getty Images
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The Rapper: Lil Boosie
When He Went To Jail: September 2009 (after he was found to be in possession of marijuana in Louisiana in October 2008 and was then later sentenced on an unrelated murder charge in July 2010)
Why It Was The Worst Time Possible: The same month that Boosie went to prison, he also released his fourth solo album, Superbad: The Return of Boosie Bad Azz. It debuted at No. 7 on the U.S. Billboard 200. But because he was sent away, he wasn’t able to tour and perform songs from the project or capitalize off the success of it. He was finally released from jail earlier this year, but it’s still TBD whether or not he’ll be able to pick up where he left off at.Photo Credit: Getty Images
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The Rapper: Lil Wayne
When He Went To Jail: March 2010 (after he was found to be in possession of a handgun in New York City in July 2007)
Why It Was The Worst Time Possible: You could argue that this was the turning point of Weezy’s career. Before prison, everything that he touched turned to gold. From his 2008 album, Tha Carter III, to his Young Money collaborative album, We Are Young Money, Wayne was enjoying success all over the place. But since coming home in late 2010, Wayne has struggled to get all the way back on his feet. It’s not solely because of jail, but jail definitely didn’t do him any favors.Photo Credit: Getty Images
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The Rapper: Gucci Mane
When He Went To Jail: September 2013 (after he was found to be in possession of a firearm as a felon in Atlanta in September 2013)
Why It Was The Worst Time Possible: Gucci has been arrested and thrown in jail so many times now that it’s hard to imagine people giving him too many more chances or relying on him to stay out of trouble. He has so much music in the tank that jail doesn’t stop him from releasing new material. But when’s the last time you got really excited about one of Gucci’s mixtape releases? Exactly. His act is getting old and it’s mostly because he can’t stay out of jail.Photo Credit: Getty Images
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The Rapper: Chief Keef
When He Went To Jail: October 2013 (after he violated his probation in Georgia in October 2013)
Why It Was The Worst Time Possible: Keef spent less than two weeks in jail late last year. But he’s unfortunately become more well-known for getting into trouble than he has for making music. And that’s putting a damper on his career as a rapper right now.Photo Credit: Getty Images
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The Rapper: Meek Mill
When He Went To Jail: July 2014 (after he violated his probation in Philadelphia in July 2014)
Why It Was The Worst Time Possible: Rick Ross has promised to help promote Meek’s new album, Dreams Worth More Than Money, if the Philly MC isn’t released in time to promote it. But that’s not going to work as well as Meek doing it himself. So he’d better hope he gets released soon so that he can get back to work.Photo Credit: Getty Images