JEAN GRAE Straight out of Xavier’s School for Gifted Youngsters.

JEAN GRAE (born Tsidi Ibrahim in Cape Town, South Africa) strikes me as one of the smartest people rapping these days. The New York emcee possesses a wit that is rare behind the mic, and when Grae gets in the zone, rhyming about packing a MAC-11 in her tote bag, she's unafraid to break the fourth wall to let you know that—pssst—she doesn't really have a gun. On this summer's Cookies or Comas, Grae hired Atlanta institution DJ Drama to host her Gangsta Grillz mixtape (an industry standard for Styrofoam-toting D-boy rappers), only for her to fire off a loose monologue about marzipan or beating your mom at Scrabble on the opening track. Not only is Grae a skilled rhymer with an immediately recognizable voice and a slithery-slick flow (her Twitter handle is "Jean Greasy"), she's a comedian—rap music's very own Wanda Sykes, whose mic skills could be well spent among the stand-up set.

In fact, it's Grae's tendency to crack jokes and break rap kayfabe that is sometimes the most interesting part of her music; she's a longtime NYC underground phenom—with fans across the globe—who craves mainstream recognition, or at least feels some pressure to achieve it. Three years ago, sometime after signing with Talib Kweli's imprint Blacksmith Music, a clearly disenchanted Grae announced her retirement from the rap game.

Considering her natural gift of rhyme and her family's deep history in music (her parents are both renowned South African musicians), nobody was surprised—yet many were relieved—when Grae reneged on that terrible promise. "I need that Grammy. I think I might be able to stop after that," she told the Village Voice at the time. Perhaps a joke, perhaps not; she frequently cites a fierce competitive urge in interviews, one of the reasons she notoriously hates being referred to as "a female emcee" or even worse, the dreaded "femcee."

The flyer for a recent date in the Pacific Northwest spoke to this, inadvertently advancing this ghettoization. In huge letters, the event was titled "WTF Is a Femcee?!" and just below that it read: "by way of Talib Kweli: Jean Grae." On a hiphop message board, few seemed to get the irony, and a couple of dudes commented that as long as she dressed sexily (oh, don't get it twisted, Jean is a sexy mutha) it wouldn't matter if she rapped Willie Nelson's lyrics. It's shit like this that Grae must deal with in her quest to be accepted and applauded, and that's why she must take such delight in skewering conventions of the culture in her under-breath asides.

In the end, though, she just might be too goddamn smart and self-aware for the kind of mainstream shine she wants. Grae's core fans treasure her, but her refusal to dumb herself down, to stop snickering at the minstrel show, to become a character—say, a "Barbie" like Nicki Minaj—means that a mainstream audience will probably continue to elude her, and thank goodness. Hiphop always needs spitters like Grae—a point made abundantly clear on Cookies or Comas' "Assassins," where she shares the mic with flow-god Pharoahe Monch and Eminem's savage sparring partner Royce Da 5'9" and proves that she can more than just hang with the boys—but what the genre really needs more of are folks who see through rap's institutional bullshit, and rise above. Burn on, Phoenix.