*20: Lil Wayne
Age: 28
2010-2011 Income: $15 Million

The lyricist reportedly wrote his first song at age 8 and signed a record deal with Cash Money a year later. Two decades later, he’s one of rap’s richest. Jail (he served eight months in New York’s Riker’s Island on a gun charge) didn’t slow him down, his new album I Am Not a Human Being topped the charts shortly after its release, making Wayne the first artist since Tupac Shakur to have a No. 1 album while incarcerated.

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