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10 Best Rappers To Drop Albums While In Jail – Penitentiary Chances

Pimp C The Sweet James Jones Stories (2005)

While Chad “Pimp C” Butler made his mark as one-half of the beloved rap duo UGK, his solo debut was marred in controversy. In 2002, The Pimp was sentenced to eight years in prison for violating his probation, which he received as a result of a previous aggravated gun charge. With the “Free Pimp C” campaign in full swing, UGK’s label Rap-A-Lot Records dropped Pimp’s debut The Sweet James Jones Stories in 2005. It was an album filled with older, previously unreleased material, placed over new beats. With little to no promo, the LP remained largely overlooked, but Butler was redeemed in 2006 when he was released from prison and dropped Pimpilation.

C-Murder The Truest Shit I Ever Said (2005)

Convicted of second-degree murder in the death of a 16-year-old fan, C-Murder recorded this entire album from prison on his lawyer’s hand-held recorder. After releasing a disc every year from 1998 until 2002, this was his first solo project since the 2002 shooting. The Truest Shit… was unable to achieve the mainstream success of the No Limit soldier’s first three releases, each of which landed in the top 10 on the Billboard Top 200, but it did hit No. 1 on the Top Independent Albums chart.

A video for the lead single, “My Life” included footage of C-Murder in jail, as well as clips of people on the outside rapping his lyrics and wearing commemorative T-shirts. This album may have been the truest shit he ever said, but the smartest shit he ever did was changing his moniker to C. Miller during a 2009 trial.

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