Year Arrested: 1999

Crime: Felony assault.

Even the top dawg execs have to (allegedly) get their hands dirty once in a while. Jay-Z was arrested for (allegedly) stabbing a record exec for leaking "Vol. 3... Life and Times of S. Carter." The leader of Roc Nation was picked up and snapped in a brown, luxurious-looking crewneck sweater and an oversized black down jacket. A far cry from the designer pieces he rocks now, but this is when Jay was just starting his climb to the top.