8. Tupac Shakur

The modern day Hip-Hop martyr also has broken wings—in 1993, he and two others were charged with sexual abuse of a female fan. In 1994, he was convicted of first degree sexual abuse, sentenced to 1.5 to 4.5 years in prison, and was bailed out by the currently-embattled Suge Knight after only serving eight months at the Clinton County Correctional Facility. He proclaimed his innocence until the day he died.

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