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Lyfe Jennings, from Prison to the Apollo Theater

Lyfe Jennings, right, at a recent concert at SOB's in New York City.
Roy Hurst, NPR /
Lyfe Jennings, right, at a recent concert at SOB's in New York City.

The music of Chester "Lyfe" Jennings has the familiar feel of old-school classics, and his soulful, gravelly voice is being compared to the likes of R&B greats Al Green and Sam Cook.

It's been a longer road than most for Jennings — he slipped into a life of crime early and spent 10 years behind bars for an arson-related charge. But on his debut CD Lyfe 268-192, released last August and beginning to climb the charts, you won't hear Jennings boasting of his criminal exploits to boost sales. Instead, the former convict, now in his late 20s, is quick to speak of the tough lessons he's learned. In fact, the title of the CD is the number assigned to him in prison.

Proof that there's power in a second chance, Jennings hit the ground running after he was released from prison in 2002. He moved to New York City to pursue a recording career, and his first stop was the world famous Apollo Theatre in Harlem.

Jennings went on to win Apollo's talent competition five times, and sealed a deal with Columbia Records. Jennings is tough to categorize — he may look like a rapper, but he plays guitar like a folk singer and croons like Motown. It's a sound some are calling "folk soul" for its raw emotion and searing honesty.

"Some people might find it unnerving, but to me, when you can win people over as a new artist — that really says something about it," Jennings says. "And you know, we've been winning them over, definitely."

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Corey Moore
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