Lyfe Jennings

Some people sneak packs of cigarettes in prison; Lyfe Jennings copped an Erykah Badu CD. And with that, everything changed, starting with the singer-songwriter's soul-searching debut, Lyfe 268-192. Named after Jennings' inmate number, it shimmers, struts, and shakes around steam-pressed beats ("Stick Up Kid"), spare handclaps ("Must Be Nice"), and slow-burning grooves ("Cry") that'll remind you of D'Angelo and Bilal's best work. In the releases since, Jennings has expanded his sound without sacrificing what made it work in the first place, from the stuttering drums of "Statistics" to the heated horns of "Mama."

Not to mention our Next Steps, a dizzying set that includes an iTunes exclusive and a chilling T.I. collab.

Just when you think you have Lyfe Jennings figured out, he spins his very own version of neo-soul — strange, surreal brushes with brassy arrangements and strangled guitars ("Biggie N***a"), steely synths and vaporous vibes ("Haters"), and a bridge that's just begging to be belted the next time no one's around to tell you just how off-key you are ("Cops Up"). And while Jennings produces most of his own material, "Brand New" proves he plays well with others, too, as skyscraping verses weave their way through twitchy loops and a T.I. guest spot that strikes a perfect balance between the streets and your bedside stereo.

When Lyfe Jennings was released from prison at the tail end of 2002, he didn't spend months picking up the pieces of the life he'd left behind ten years before. The Toledo native took to the streets of New York instead, scoring the top spot at the Apollo Theater's Amateur Night and selling towering stacks of his self-produced demo. But he wasn't without a label for long. As our filler-free playlist proves, Jennings has delivered four boundary-breaking albums in just six years, from the cleansing choruses of his Lyfe 268-192 debut to the hopeful hooks of I Still Believe, the album Jennings has called his last. Here's hoping he's wrong in the end, although there'll be no stopping songs like "Let's Stay Together" and the Snoop Dogg-backed "Old School" in the meantime.