Crime: Second-Degree murder, Two Counts of Attempted Murder, Assault, Illegal Use of a Firearm, and Criminal Possession of a Weapon
Verdict: Guilty 
Sentence: Served five years at Rikers Island in New York.

The trouble started when the flashy, English-born Slick Rick hired his cousin, Jamaican-born Mark Plummer, as a bodyguard. But soon, his bodyguard tried to extort him. Rick fired him, and Plummer responded by sending some of his friends to rob the rapper. Rick refused; they threatened to kill him and his family. Later on, he would find bullet holes in his front door.

Rick began to collect guns, believing that he could only protect himself through self-defense. On July 3, 1990, the rapper was alerted that Plummer was in his neighborhood. Armed and sitting in the car with his pregnant wife, Rick hunted for Plummer. When he found him, he accidentally shot an innocent person, before striking Plummer in the foot.

A police chase ensued; the rapper crashed into a tree (breaking both of his girlfriend’s legs), pleaded guilty, and went to jail for three to 10 years. Within a year, Plummer would be shot dead. Rick’s time in jail sidelined his career completely. But the rapper did release one of the more inventive music videos about incarceration. 1994’s “Behind Bars” was necessarily animated.

Rick wouldn’t leave prison until 1996, one year after recording this interview with Russell Simmons. His run-ins with the law weren’t over; Rick had never applied for citizenship in the United States, and in 2001, after performing on a Carribbean Cruise, the rapper was detained.

Due to his felony conviction, he faced deportation. In 2008, however, New York governor David Patterson granted Rick a full pardon on the attempted murder charge, taking the pressure off of his immigration problems.