It's a muggy Thursday night and Jarren Benton, sweating in red leather pants and a black t-shirt that says "Dope" in scarlet letters, is on the sidewalk killing time before his headlining performance at the Knitting Factory in Brooklyn. As a nervous fan spits rhymes to him, Jarren nods along in encouragement and flashes the same impish smile you may have seen at the beginning of the insanely violent (and popular—over a million views and rising) video for his song "Skitzo." When the fan finishes freestyling Benton drops a brief, joke-y couplet about wanting to get a bagel in Brooklyn—and then he's gone.

Sitting at a small table in a dimly lit bar nearby, he says he's only now getting used to having fans who are so excited to see him that they push their material on him. He's sympathetic to their plight because he used to be that guy. He annoyed Puff Daddy at a mall in his home state of Georgia when he was 15. He did the same thing to Raekwon at a concert in Atlanta when Only Built 4 Cuban Linx... first came out, only to be scared away by Inspectah Deck. As he sips a cranberry vodka, Benton remembers the pain and embarrassment of that moment. "That fucked me up," he says. "I don't wanna be a dick about this shit. I understand you can get your feelings hurt—your dreams get crushed."

Dreams have been coming true lately for the 31-year-old rapper. After toiling in obscurity for years—working odd jobs as a dental assistant and as an exterminator—the married father of two is enjoying a modicum of mid-level hip-hop fame. Off the strength of gross-out videos for tracks like "Skitzo" and his vividly titled 2011 mixtape Huffing Glue With Hasselhoff, he signed to Hopsin's Funk Volume in 2012. The collective has been compared to other ascendant California hip-hop groups Odd Future and T.D.E., but in the last couple years they've carved out a distinct niche by mixing hard-hitting Eminem-esque lyricism with the independent-minded business model of Tech N9ne. In June, Benton released an album, My Grandma's Basement, and in September he'll play Rock The Bells with labelmates Hopsin and Dizzy Wright before heading out on another tour with Strange Music affiliate Rittz and rising female rapper Snow Tha Product. Things are coming together.

That doesn't mean Benton feels particularly comfortable or economically stable at his current level of success. "I'm 31," he says, "That's a lot of time in the rap world." But Benton doesn't sound too nervous. "A lot of niggas in the game are popping in their 30s," he notes. "What's Rittz? 33 or 34? Danny Brown is 31." (Rittz and Danny Brown are actually both 32, but you get his point.)