Rockie Fresh
Rockie Fresh

It’s been a big year for Rockie Fresh. The 19-year-old rapper entered 2010 untested, having just released his debut mix tape, the spotty but promising Rockie’s Modern Life, which got his name onto local hip-hop blogs like Fake Shore Drive for the first time. He’s heading into 2011 a full-time artist, with some big-name endorsements from the Chicago hip-hop scene and beyond. His second mix tape, The Otherside, came out two weeks ago, and it’s already inspired Urb magazine to call him “the Derek [sic] Rose of rap Chi-Town has been waiting for.”

This is especially impressive when you consider that Rockie, aka Donald Pullen, had only been rapping for about a year when Rockie’s Modern Life dropped and didn’t set foot on a stage till April 2009. When he was growing up, in the late 90s and early 2000s, hip-hop was at the last peak of its gangsta-capitalist phase, so it took a sea change in the music to convince him there might be a place in it for somebody as unthuggish as he was. “When I was coming up, you know, gangsta rap was really relevant. I was raised in the suburbs, you know. I’m not a gangster or anything like that. So I just always had the preconceived notion that that was what being a rapper entailed. And when guys like Kanye and Lupe broke into the scene, it really made me feel comfortable with my story.”

Basically Rockie is a smart, polite, friendly kid who still lives with his parents in south-suburban Homewood, and the fact that he doesn’t try to hide that in his lyrics, in his image, or in his conversations with journalists is one of his more endearing qualities. It may also have something to do with the way he’s been embraced by so many better-known figures in Chicago rap. YP and Big Homie Doe, for instance, appear on his track “Fly Like This.” Promoter Hustle Simmons got him the bill at October’s Lil B show at the Wild Hare. And Vic Mensa, Hollywood Holt, and Mikey Rocks of the Cool Kids all supported Rockie by opening for him at the Otherside release party last week.

“A lot of people live by ‘You have to give respect to get it,'” Rockie says, and he includes himself among them. Hungry young rappers tend to come out of the gate in attack mode, trying to grab attention, but that’s not his style. “When I came onto the Chicago rap scene, my goal wasn’t to be this kid that everybody feared or was intimidated by,” he says. “I just respect all of these guys and what they do. These guys are really good artists, and so it makes it real easy for me to show respect towards them. And in turn they just give me the same thing back.”

One of the most important relationships Rockie has built is with Kidz in the Hall rapper Naledge, who donated a verse to one of Otherside‘s standout tracks, the rolling, string-soaked “Living.” Naledge “has sort of played a mentor role in my career,” he says. “He calls me every now and then and drops some knowledge on me. He knows what he’s talking about.”

Naledge discovered Rockie by polling friends about younger rappers to look out for—he mostly does 21-and-up shows himself, which makes it hard for him to stay in touch with the under-drinking-age crowd. Their first real interaction was at the Modern Life release party in December 2009, where the older rapper took the stage for an impromptu performance. “He was a name that kept popping up,” Naledge says. “He reminded me a little of myself. His work ethic was there. It intrigued me a bit. I’ve seen a big evolution in what he’s doing. He kind of went from this super-duper young mix-tapey rapper to finding his own sound and finding his own voice.”

On Modern Life Rockie comes across like a hyperactive, Nickelodeon-loving adolescent, but that aspect of his persona is largely absent on Otherside—now he sounds like a full-blown rapper, all focus and determination. Though he hasn’t lost his charming earnestness, most of the new mix tape’s lyrics are about his nonstop grind and his conviction that he’s about to break out. He refers to his off-hours life with just a couple of lines about the avidity of his female fans and one or two mentions of smoking weed. He’s still a bit green as a lyricist, but when it comes to flow he’s as fully developed as any of the post-Kanye rappers he’s bound to be compared to—Drake, J. Cole, Kid Cudi. And his lyrics show the potential for sophistication, with the occasional line that takes a second to process: on “Sofa King Cole” he says of rap fans, “Hopefully they will learn to chill with all that wack shit / I see ’em hangin’ with them squares like Patrick.” (OK, so he’s still into Nickelodeon.)

The most striking aspect of Otherside—the one most likely to set Rockie apart from all the other baby Lupes and Kanyes—is its overall sound. Mix tapes, especially mix tapes by novices, tend to be grab bags of beats, some jacked and some donated by producers who didn’t consider them bankable enough to offer to rappers working on label-backed projects. All the music on Otherside, however, is the work of local production duo the Cartoonz. They mine the vein of charcoal gray moodiness Kanye opened with 808s & Heartbreak, and like him they play styles and textures against each other—pairing, say, velvety strings with chanted heys that may as well have come from a Young Jeezy song. More important, the Cartoonz have a pop streak a mile wide, and they indulge it on cuts like the glimmering, AutoTune-inflected “They Don’t Understand Why,” which is just the kind of song that puts dollar signs in A&R agents’ eyes.

Naledge is confident that Rockie can make the difficult leap from Chicago to the national stage and find the kind of mainstream audience that’s embraced Lupe and Drake. “The greatest thing he has going for him,” he says, “is that he’s built this local following. That’s the greatest thing that a label will want to see—that you’re capable of filling up a room on your own. That’s how Wiz started. That’s how the Pac Divs of the world, the Cool Kids, that’s how we started.”

When I ask Rockie whether he’s talking to any labels, he explains that he’s got to keep that information confidential—but given the way he brightens up at the question, it certainly looks like someone’s been showing interest. “I really can’t say too much about that,” he says. “But you know, we’ve got a while to go. I’m still not anywhere near as big as I want to be.”