Nigel Holt doesn't want you to pay for his music. At least, not yet: "if people don't know who the fuck you are, you have a lot of nerve being like 'Check out my music, AND buy it.'"

Influenced by old school rap with his totally '80s flow and his spare, bass heavy beats, Hollywood Holt raised his profile the new school way: mixtapes and MySpace. His tongue-in-cheek lyrics about girls, parties and skateboards are helping make Chicago an epicenter for left-of-center hip hop with artists like The Cool Kids, Kid Sister and Kid Cudi. According to the twentysomething: "the gangsta shit is old, the ballin' shit is old, all that shit is old."

Purveyor of all things "cool," Kanye West appears to agree. West co-signed for the twentysomething by posting Holt's video, Hollywood, on his popular blog.

The founder of the Murder Crew – the "first black-founded moped gang in the country" – Holt and producer Million $ Mano flipped Rich Boy's Throw Some D's to create Throw a Kit, a memorable ode to their nerd wheels. His mixtape, Holt Goes to Hollywood , features more good-humored verses over beats from underground artists like Feist, Mic Terror and MY!GAY!HUSBAND!. On the strength of his mixtape and high-energy live shows, Holt has rolled through Lollapalooza and the CMJ's Music Marathon, sharing the stage with acts like Lupe Fiasco and Dizzee Rascal.

Confident and sarcastic, Hollywood Holt is currently working on his debut album: "It's going to be the best album of all time, ever."

See: myspace.com/holtgoestohollywood

In less than one year, Melisa Young, the fresh-faced rapper known as Kid Sister, has become the "it girl" of hipster rap. It probably didn't hurt that the Chicago native also happens to be the girlfriend of Canadian cross-fade master DJ A-Trak (Kanye West's official DJ), who produced her Pro Nails, a J. J. Fad-by-way-of-Houston club jam that effectively displays Kid Sister's old-school flow. Kanye has even "co-signed" for Kid Sister by kicking a verse on that synth-heavy track and including it in his Can't Tell Me Nothing mix-tape.

But the 27-year-old Young built her rep the hard way by promoting parties for hipsters and rapping alongside Flosstradamus (her little brother's DJ-slash-production team) with a spitfire attack that falls somewhere between Missy Elliot and Lil' Mama. With only six tracks – including Control, an electro-rap with an infectious call-and-response chorus – Kid Sister has already graced the cover of influential music magazine URB. Not bad for a twentysomething who not too long ago was working at a children's clothing store and babysitting to pay the rent.

Kid Sister, whose look is in line with the current taste for wildstyle colors and retro cuts, is currently putting the final touches to her debut album, Ko-Ko B. Ware (named after the beloved '80s WWE wrestler), to be released later this year. Until that happens, Young will be on tour with A-Trak and kid brother Flosstradamus. The family that jams together, stays together.

see: myspace.com/kidsister