10 Rappers Who Went To Jail At The Height Of Their Career

While “street cred” is of great importance when it comes to the success of a rapper’s career, it’s a little difficult to be a lucrative artist when you’re behind bars. Going to jail is hardly a career booster, even though spending some time “away” can make a rapper appear edgier in the music industry. A rapper’s time in jail can even create more media buzz in some cases, which can lead to more popularity when it’s time to put another album out. There are several reasons why rappers could be arrested, and in many cases, their art imitates life, or vice versa. Some rappers have gone to jail for minor offenses, while others have been involved in serious crimes that have dire consequences. Either way, getting arrested and going to jail  is a serious gamble that may not work out so well in the long run.

Another reason why going to jail shouldn’t be a substantial part of a rapper’s pathway to success is that it can be difficult to continue with a music career once a rapper has been out of the public eye for some time. Here are 10 rappers who were incarcerated during the height of their careers.


10 Mysonne

Ever heard of Mysonne? If you only listen to the most current hip hop artists and haven’t been following the music genre for long, then there’s a good chance you don’t know who the rapper is. The rapper got 7 to 14 years in jail when he was arrested in 1999, on two armed robbery charges. Mysonne was a Def Jam artist who was getting ready to release his debut album, Life Teaches and Reality Bites, when he was arrested. The project was put on the shelf until 2006, when Mysonne was released. He has tried to resurrect his rap career, but has had little luck.

9 Max B

It’s likely that many music lovers, including some hip hop heads, have never even heard of Max B. The rapper was at the height of his new career due to his mix-tapes, which are referred to as the Coke Wave series. Max B was sentenced to 75 years in prison, due to a 2007 incident that resulted in a murder in a Florida hotel room. The murder was linked to a robbery, and Max B received his sentencing in 2009. There’s a good chance the music industry won’t be hearing more from the rapper, due to the length of his sentence.

8 Shyne

In 2001, Shyne was sentenced to jail for his involvement in a 1999 club shooting in New York that involved Sean “Diddy” Combs and Jennifer Lopez. He was seen as the next big star on the Bad Boy record label, but his legal problems derailed this. He released an album in 2004 called Godfather Buried Alive, but he is still trying to revive his career, even after his release from prison in 2009. It may be time to choose a different career path, since it’s likely that people are always going to associate him with “that shooting” and refer to him as “that rapper that went to jail a long time ago.”

7 Slick Rick


In 1990, the British rapper was sentenced to five years in prison after he shot his bodyguard (who allegedly tried to have him killed) and an innocent bystander. Two years before this incident, the rapper was experiencing vast success as a result of his album, The Great Adventures of Slick Rick. Before he served his time, he released an album entitled The Ruler’s Back, and he recorded enough material so that Def Jam could release his project, Behind Bars, in 1994. However, the last two albums didn't have nearly as much success as his first project. After Slick Rick’s release from jail, he was deported, but he was pardoned in 2008.

6 Cassidy

Cassidy’s second album, I’m A Hustla, was released at the same time he was experiencing legal trouble. In 2005, Cassidy was involved in a shooting and a judge sentenced him to 11 to 23 months in prison after he was charged with involuntary manslaughter. While the album did sell pretty well, it was not as successful as his first album, which included the club anthem Tipsy. Cassidy did release B.A.R.S (The Barry Adrien Reese Story), which was his third album and least lucrative project. He has been trying ever since to regain the popularity he once had.

5 Remy Ma

This female MC, formerly of the Terror Squad, was sentenced to 8 years for several crimes, including the shooting of one of her former friends. It is alleged that Remy Ma shot the woman in the stomach during an altercation. At the time of Remy Ma’s arrest, she was arguably one of the biggest female rappers in the music world, and her association with Fat Joe’s label had a lot to do with this. It is highly unlikely that the MC will be able to regain her spot, especially with the appearance of new female rappers who are continuing to gain popularity, such as Nicki Minaj and Iggy Azalea.

4 Gucci Mane

Gucci Mane served a 6-month jail sentence in 2005, for physically assaulting a concert promoter in 2004. In 2008, he had to go back to prison because he failed to complete the community service and probation requirements associated with the case. In 2010, Gucci Mane was arrested and spent time in jail because of traffic-related offenses. The following year, he was arrested again on battery charges. Obviously, it’s been a challenge to maintain a substantial rap career amid all the legal troubles. The rapper has been working on new music, but his arrests and jail time make it hard for him to promote projects and book performances. However, his arrests did help to fuel the success of his 2009 album, The State vs Radrick Davis.


3 T.I.


T.I. is a rapper who is also known for his business moves and movie roles. Unfortunately, his multiple stints in jail have also made him more well-known. His most notable sentence was in 2009, when he was ordered to serve 366 days in prison due to federal weapons charges. The rapper’s 2008 album Paper Trail, his 2010 No Mercy and his current project entitled Trouble Man, were either composed while he was being sentenced or shortly after he was released from jail. He’s completely free of all charges and has even starred in a VH1 reality show with his family. It remains to be seen whether T.I.’s career will completely revive itself, although he seems to be doing quite well.

2 Lil Wayne

Lil Wayne is arguably one of the most popular rappers in the industry right now. However, the artist has had his share of run-ins with the law as well. Two years after he was found to have an illegal weapon in New York City, he was arrested in 2009. He began his one-year sentence in March 2010. He was released later that year, and his album, Tha Carter IV, was available to the public that same year. He has also been in the public eye due to his love for skateboarding. Lil Wayne’s record label, Young Money, also generates a number of profits for him. For instance, two of his most noted artists, Nicki Minaj and Drake are both doing quite well.

1 2Pac

Tupac Shakur, or 2Pac as he is affectionately known as, was and is a very influential figure in the rap industry. He was sometimes known for his thought-provoking  and community-minded lyrics, but recorded his share of thug rhapsodies as well. In 1993, he and his associates were accused of sexually assaulting a woman. Due to this, he was sentenced to 1.5 to 4.5 years in prison. Surprisingly, this sentence didn’t cause too much damage to Shakur’s career. His album, Me Against the World, was released while he was incarcerated. He also got a spot on Death Row Records, because the record label’s CEO, Suge Knight, paid for Tupac to be released from jail.



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