24. The People of the State of New York v. Earl Simmons (2004)
Crime: Cocaine Possession, Criminal Impersonation, Criminal Possession of a Weapon, Criminal Mischief, Menacing, Driving Under the Influence of Drugs or Alcohol, Claiming To Be a Federal Agent, Attempting to Carjack a Vehicle
Sentence: Served 40 days at Rikers Island in New York.
DMX has had recurrent run-ins with the law. But it was his June 2004 run-in at Kennedy International Airport where it became apparent that DMX’s substance abuse and legal problems were spinning out of control.
The rapper claimed to be a federal agent, stole a car, and ended up being charged with those crimes as well as driving under the influence, possession of a controlled substance, and possession of a weapon. The rapper ended up pleading out to a 40-day sentence at Rikers Island, versus the year in prison he would have faced had he taken the case all the way through trial.