Date: January 2002
Rest in peace to the legend, of course, but still: Chad Butler sat behind bars for falling behind on his community service commitments, the result of a conviction for assault after he flashed a handgun at a woman at a Texas mall. He spent four years (!) in prison. With Pimp C behind bars, his UGK partner Bun B made "Free Pimp C," one of the most ever-present catchphrases in early-Aughts rap music.