2. DMX

If there was one rapper we would say was the most hard-core, it would be DMX. It’s not only that he has the longest criminal record amongst rappers, but also the variety of his criminal activities.

Earl Simmons, a.k.a. DMX, is better known for his illegal deeds than for his career in music. It seems like the rapper tried to get arrested for everything he could – from felony drugs charges and reckless driving, to cocaine possession and criminal impersonation.

DMX’s most notorious crime happened in 2004, when he managed to crash his SUV through a parking lot gate at New York’s Kennedy airport, but only after he told the security guard that he was in fact an FBI agent.

Total number of arrests: 13