7 dope rappers whose criminal lifestyle jeopardized their hip hop career

In Hip Hop by Alasdair Kennedy

7 dope rappers whose criminal lifestyle jeopardized their hip hop career

We all know that gangster lifestyles and hip hop culture have had a lot of cross over in the past. If it’s not a gun charge it’s a narcotics conviction…. and so on. Hollywood celebrities can arguably get away with a lot more than the rest of us (largely because they can afford the best lawyers) but these seven rappers tested their luck when it came to their criminal lifestyles, and luck didn’t turn in their favour… 

Beanie Sigel

Talented Philly lyricist rapper Beanie Sigel has been in and out of prison most of his career, the most frequent charge being possession of firearms. On August 29, 2012, Sigel was arrested after police found a fully loaded handgun, $4,500 in dollar notes, an unlabelled bottle of codeine and an assortment of other drugs. He’s currently serving time for failing to file tax returns and possession of drugs.


In 1999, just before the scheduled release of his debut album, Belizean hip hop artist Shyne was charged with and convicted of attempted murder, assault and reckless endangerment after a shooting took place at a Manhattan club which left three people injured. He ended up serving 10 years in prison and has since been deported from America. Although witness reports from victims claim seeing Shyne holding a smoking gun at the scene, a handful of conspiracists believe the 21-year old rapper had nothing to do with it and that he acted as a fall guy for P Diddy.


Now a registered sex offender, Mystikal hasn’t had a great history when it comes to women. In 2003, he was charged with six years in prison for sexual battery and extortion. In 2012, he charged with domestic abuse. Although he got off on bail, he was jailed for 81 days for violating his probation.


In 2011, pioneering English rapper and UK hip hop figurehead, Skinnyman was arrested after he tried to ram his girlfriend’s car off the road before attacking her vehicle with a hammer. He spent 16 months behind bars.

Tupac Shakur

Throughout his career, Tupac was accused of all manner of misdemeanours, including shooting a police officer in the buttocks and attempting to hit fellow rapper, Chauncey Wynn, with a baseball bat. Most infamous was a sexual abuse charge, which he denied adamantly in court. His multiple conflicts with other rappers are often believed to have prompted the drive-by shooting that led to his tragic death.

Ol’ Dirty Bastard

Wu-Tang Clan member, Ol’ Dirty Bastard, was notorious for getting on the wrong side of the law and served numerous jail sentences throughout his life. In October 2000, he escaped from a court-mandated drug treatment facility and spent one month on the run. His time as a fugitive and his criminal lifestyle earnt him a reputation as a ‘Robin Hood’ figure amongst fans. His relationship with hard drugs however had its consequences and in 2004 he died of an overdose.

Steady B

Steady B’s career was waning in 1996 – so he tried to rob a bank. The bank robbery was a failure and Steady B ended up shooting and killing a police officer for which he was given a life sentence. The musician is still serving time.