Pimp My Life 

A lesson in hustling and marketing with Pittsburg emcee the Jacka.

It's a Saturday afternoon, and a sleek Cadillac CTS prowls the streets of the East Bay. The driver, PK, is a slight, well-mannered guy with lazy doe eyes. Officially dubbed a manager, he's kind of an all-purpose administrator, chauffeur, and PR liaison for the guy sitting next to him: an emcee who calls himself the Jacka. In the time it takes to drive from West Oakland BART to the Emeryville Public Market, Jacka gets at least half a dozen phone calls, including one from a promoter looking to book a show that night. He nudges PK. "Wanna drive to Eureka right now? They say $400 when we get there, and $400 at the end of the night."

PK nods grudgingly, rolling his eyes a little. He'd already made plans for the evening, but he'll cancel them. "If I had a new girlfriend or something," he later admits, "she'd definitely leave me."

"Awright," Jacka tells the promoter. "We might fuck wit it."

Jacka's life appears to be a long, endless string of hustles, a skill he learned early on. Born to fourteen-year-old parents, Jacka grew up poor enough to consider meat a luxury menu item. He started selling crack at age eleven, cutting his teeth at a downtown Oakland recreation center where first-generation immigrant teens copped dimebags on the way to their ESL classes. Pretty soon Jacka's game was so tight he became the main breadwinner for his mom and little sister; he pretended to work a series of lucrative odd jobs while attending high schools in Oakland, Richmond, and Pittsburg. At fourteen, Jacka discovered heroin; a friend taught him how to get high by mixing smack and water in a Visine bottle and snorting it. A couple of years later, he was hooked. Jacka also started robbing and burglarizing — the emcee's name derives from his talent for jacking other people's shit.

It took the deaths of several friends and a conversion to Islam for Jacka to come clean: Now he parlays his hustle and hard-knock life into rap music. He and his Pittsburg-based high school crew the Mob Figaz — also including Husalah, Fedx, AP 9, and Rydah J. Klyde — met famed Sacramento rapper C-Bo in a local record store back when they were all sixteen or so; the crew followed him to the studio that very day and recorded the track "Ride 'Til We Die." Ever the impresario, Jacka quickly realized that in a genre so preoccupied with authenticity, he could make his authenticity his occupation.

But that actually isn't the emcee's main selling point. What's most intriguing about Jacka is that he's so good at inhabiting his own melodrama — he really is that hip-hop-generation Candide who gains virtue by suffering. And in the rap game, a hardscrabble life doesn't just ensure street credibility. It's also sexy.

Jacka's rap persona is cagey, thick-skinned, and cold-blooded: On the opening cut of his 2005 album The Jack Artist, the emcee raps, I felt nothing, man, it's really nothing/It's been so long since Jacka felt something. But he still doesn't come across as a Dragnet-inspired crook or grimy desperado. In fact, his songs sound credible and revealing, sometimes even cathartic. The track "Never Equal" — about the futility of being a top dog in a 'hood that still exists at the margins of society — serves as an exercise in self-flagellation: Please forgive me for my deepest thoughts/I took advantage of my people where the weakest walk ... I'm upset a lot, I'm obsessed with Glocks. At his tenderest moments, Jacka talks openly about addiction, anger, and regret, basically purging all the insecurities he has always strained to conceal.

Jacka sets these aggressive, bruising raps against soft, groove-driven hooks — deliciously sentimental piano samples and women crooning sweetly over R&B string sections — meant to shore up the pathos in stories about slinging dope and shooting clips. It's the same tack Biggie Smalls tried with the lyric You bleed lovely, slugs go touchie touchie: Indulge your audience's thug fantasies and recast them in a classical melodramatic template, the violence and the romance intertwined. Ultimately, the most seductive thing about The Jack Artist is that it lends itself so well to voyeurism. Jacka regales his listeners with a virtual safari through the seediest ghettos in the East Bay, but also allows them the guilty pleasure of worming into someone else's interior world.

Considering the recent spate of hip-hop "blockumentary" films, it seems a lot of rappers see big paper returns in the ghetto tourism racket, but it isn't always clear whether the idea is to tell your story or just get paid. On the afternoon they're summoned to perform in Eureka, PK and Jacka are recuperating from a video shoot for My Block, a new MTV2 reality show spinoff in which East Bay rappers like Keak da Sneak and Mistah F.A.B. are filmed posing with friends in their real-life 'hoods, giving suburban audiences a taste of ghetto life without ever having to leave the comfort of their own homes. Jacka — who says he used to ogle the swaggering, blinged-out rappers on TV until he realized they were poaching their style and attitude directly from the dope dealers on his block — is definitely no stranger to the game. Still, he seems a little ambivalent about participating in his own exploitation. Describing the shoot, he can't hide a tinge of sarcasm. "I got interviewed, you know, the normal shit," he says. "Smoking weed, being cool, showing love."

While Jacka isn't averse to pimping his ghetto background for profit, he takes his cultural ambassador role with a grain of salt — this cat is definitely not the hip-hop counterpart to JT LeRoy or James Frey. The emcee is generally not inclined to meet commercial demands, and says that the DJs at KMEL and Wild 94.9 are irritated with him for not minting club-friendly bangers or hyphy shit. "I try not to listen to Top 40 rap because I don't want it to rub off on me," he explains.

Jacka is also fairly critical of the excesses in mainstream hip-hop. Peering at a picture of the BET-wooing emcee Trina on the cover of Ozone Magazine, he marvels at how the artist appears to have lost her ass since she entered the national market. "That's what happens when you get hit too many times," he admonishes. (Jacka admits, however, that you'd have to shag a lot of people to lose that much ass: "Somewhere in the 1,000-1,500 range.")

Jacka is canny around the media; he approaches mainstream popularity with his own reservations and his own personality. But he's still a hustler at heart. In Emeryville, he and PK grab a meal of Chinese food, orange soda, and Arrowhead Mountain Spring water, call their weed dealer to make another take-out order, and heel up for the ride to Eureka. They've got a few swishers and a store of high-octane energy drinks for the road; PK sparks a blunt in the car, already knowing it's going to be another long Saturday night. And Jacka's cell phone hasn't stopped ringing.

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