2. Ja Rule
MTV Video Award winner, Ja Rule did not filed taxes on his income from 2004 to 2008 and thus paid the ultimate price by landing up in prison. He was handed down a 28 month jail sentence for owing over $1.1 million in penalties and tax debts. The actor and rapper served his sentence of tax evasion along with a separate sentence of gun possession due to a 2007 incident. He was finally released from jail in May 2013.