Coolio, the popular American rapper, died Wednesday, at 59. His track Gangster’s Paradise made him famous worldwide, and the rap speaks of life on the streets while managing to carry a tone of redemption. Rap has often been associated with drugs and violence, much of which comes from the lyrics of the song, but Coolio – who eventually moved to Compton, seemingly kept these elements out of his music, consequently helping take hip-hop to the mainstream in the 90s. 

That said, Coolio was no choir boy either, and had his share of run-ins with the law. 

1998 

Coolio was charged with punching a saleswoman in Stuttgart while touring Europe. The Grammy winner and his group reportedly left the boutique with items worth $940 and the rapper hit the woman when she confronted them. 

However, Coolio said, “It was understood that the clothes were in exchange for the autographs”, adding that he had offered to pay but the store would only take cash, and not his credit card. 

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In September that year, Coolio was arrested for possession of marijuana and a firearm, after police pulled him over on the wrong side of the street. 

2001

He was convicted in 2001 for carrying a concealed firearm in a vehicle.

2009 

Coolio was arrested at the Los Angeles International Airport, in March, and charged with possession of crack cocaine and battery. Security found a crack pipe in his luggage and the battery charge was tagged on after the rapper allegedly grabbed the security officer’s arm when his luggage was being searched. 

2012 

Coolio was in Las Vegas jail after cops pulled him and his friend over for a routine traffic violation. The Gangsta’s Paradise rapper got the short end of the stick since he had two active bench warrants for numerous traffic violations. Despite being in the passenger’s seat that day, the cops did not take it easy on Coolio, sending the rapper behind bars. 

2013 

Coolio faced domestic violence charges for allegedly beating his girlfriend and the mother of their child. However, these charges were subsequently dropped. 

2016 

Coolio was detained for carrying a loaded, stolen firearm. As a convicted felon, he is not allowed to carry guns. He pled guilty and was spared jail. 

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Prior to the hearing, the rapper had said “I do not condone the use of firearms legal or illegal”, adding, “I don’t do crime”, Los Angeles Times reported.