Gangsta-for-life Mavado also considers himself a Rasta—"a gangster for Jah." Even when he's lyrically filling coffins, his intonation carries such anguish, it's hard to argue that he's wholly glorifying violence. His current hit, the stunningly spiritual paean "On the Rock," is bona fide church music, stirring enough to inspire fans, hot enough to lure Jay-Z onto the remix.

Contradictions in dancehall are as abundant as pum-pum shorts in a Kingston club. Vybz Kartel talks guns and graves with the best of them, but recently recorded anti-violence public-service announcements. On one track, Busy Signal spits lyrics like "wuk gal, bust guns, smoke weed"; on another, he talks about never going to jail again (he spent nine months there in the U.S.), which he sees as "a positive movement" that will "make the youth dem know that jail is not a tourist resort—it's not a graduation or a degree." Sizzla is on the one hand a picture of Rasta piety—his latest compilation, The Journey: The Very Best of Sizzla, showcases tunes whose titles alone bespeak self-help values ("Ain't Gonna See Us Fall," "Be Strong," "Thank You Mama")—and, on the other, a man who delivers lyrics like "big long gun run up 'pon dem," and whose entourage beat up another artist at a show last fall. In Jamaican music, the good and the bad are longtime bedfellows.

Lesson #5: Gangsters usually mellow with age.

What do Ice Cube, Ice-T, Snoop Dogg, and Flava Flav have in common? All were once boogeymen to the American public, gangsta-fied corrupters of youth—and all are now well-lodged in the American mainstream via movies, network dramas, and reality TV. Give Mavado, Munga, and others time (and the opportunity to expand their perspectives beyond their blocks and beyond Jamaica), and they'll likely do the same.

After our interview, Mavado invites me to preview tracks from his upcoming album, tentatively titled David Constantine Brooks: Better Tomorrow. "I'm still singing about gangsters and all of that," he says. "But I'm doing more teaching—about righteousness. Actually, that's the name of a song on it. If you want to teach the youths, you have to start from somewhere. You have to get the youths to listen to you."

A striking cross between a little boy—small, sweetly mannered—and an old man (his face is worn, weary, and scarred), Mavado scrolls through track after mournful track; I hear few mentions of bullets and brawls. Meanwhile, he mentions his charity, Connect Jamaica (which provides computers to schools on the island), and the school he built up in his neighborhood. He complains that the legal drama and visa trouble have distracted him from doing "all the positive things I want to do." Time will tell if he'll be able to do them, but if hip-hop history is any indication, the outlook is murky indeed.

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