Rich Seng, creator and producer of Rhyme Spitters II, the freestyle battle tournament that took place last Saturday, was so confident about his favorite MCs that he had a couple camera crews for an upcoming DVD trailing them at ten in the morning. Prime, T-Scar, Jah Safe, Vitamen D, Shamgod, Jargon, Jitu–he expected them all to advance to the finals at the Note that night. But crowds always love to cheer on an underdog, especially one who can shake up a veteran. Only one of Seng’s freestyle titans, 25-year-old Jah Safe, made it to the final four. And he ended up pitted against an unlikely opponent–20-year-old Sketch 185, a junior at the American Academy of Arts who’d already been eliminated earlier in the day.

The first Rhyme Spitters tournament, last summer, drew 64 competitors. This year the number jumped to 160, and the prize money doubled from $1,000 to $2,000. The initial rounds were held under the hot sun in Wicker Park, where contestants swarmed around four battle stations. An MC named Alpha Male got laughs from the crowd when he shot at a competitor “You’re dumber than not doing this shit in the shade!” Battlers faced off one-on-one: the first would rhyme for 30 seconds–timed by one of the judges’ cell phones–then his opponent would have 30 seconds to retaliate, and then they’d repeat the process one more time, for the most part working without musical accompaniment. The rounds lasted until the 160 were cut down to 32. By then, Seng, who runs the production company Cherry Bomb, had 16 cameras shooting the action.

Two of Seng’s picks, Jargon and T-Scar, lost their very first battles. T-Scar, who’s 19, was a crowd favorite last year, coming in third based on his ability to exploit the appearances of rival MCs. Last year’s champion, Vitamen D, was out after his second battle. The road to the Note was smoother for Jah Safe. “I showed one of my blades, they showed their blade, and somebody’s blade wasn’t quick enough,” he says. “That’s all it was.”

Sketch 185, a south-sider whose real name is Willie McIntyre, got knocked out in the first round, though he takes issue with the judges’ decision. “As far as I know I served him. The crowd even believed I served him,” he says about his rival. “But I guess the judges decided that I lost. And I got eliminated even though the crowd booed the judges for their decision.” After the preliminaries Sketch was hanging out with his friend Fonzi, who had earned a spot at the Note. “We went back to his crib, drunk a couple beers, just relaxed,” Sketch says. “And he got the news while we were chilling just listening to beats that his aunt had just died in a car crash.” Fonzi scribbled down a note to Seng explaining why he wouldn’t be able to perform and gave Sketch the wristband used to identify competitors. “He told me, ‘Yo Willie, tonight you’re Fonzi,'” says Sketch.

It took 31 battles to whittle the 32 finalists at the Note down to one champ. A DJ was now providing backup for the freestyles. When the skills of two MCs were too close to call, judges and audience alike would call for an extra round where competitors traded blows every four bars instead of every eight.

Sketch was just hoping to make it past round one. The “one thing I had in my mind was, no matter what, I have to win the first battle,” he says. “If I go through this and my boy goes through that and I don’t make it past at least the first round, it almost seems in vain. . . . I just felt that I owed it to him.”

Sketch wasn’t charming or polished–he even had trouble holding the mike close enough to his mouth, making it hard to catch his lines at times. But he had a knack for going after his opponents with startling, scrappy ferocity. When his battle with Sam I Am in the second round went into a tiebreaker, he rapped, “Wanna mess with me? You’ll rap in your seat / I could do a cartwheel through the gap in your teeth.” Slowly he began winning over the crowd.

Jah Safe couldn’t have been more different. He was so comfortable onstage he seemed almost lackadaisical at the beginning of his rounds. But invariably, as his opponent did something to get under his skin, he would retaliate with a furious but fluid outburst. When Charlie Vegas taunted him by pointing out a stain on his shorts and claiming it was semen, Jah snapped out, “When I come through I’m testin’ you dudes / Tear out your ass like Mexican food / You don’t want to floss with me, dude I’m better than you / Better yet, I show a rookie how a veteran do / Better yet, when I come through I’m severin’ you.”

Meanwhile, more of Seng’s favorites were getting axed. Prime, who’s been on HBO’s Blaze Battle, went down in his first round against Drunken Monkey, a growling MC who stalked the stage and kept referring to himself as a disease. Jitu, a veteran who was last year’s runner-up, was pounced on by a much younger MC named Kaorezem, who immediately attacked his age: “Yo, great-granduncle about to get faded / Thirty-nine years old still ain’t made it.” Shamgod, perpetually fingering a black cigarillo, seemed too disgruntled to enjoy himself. When his quarterfinal battle with Jah Safe went an extra round he dissed Jah’s T-shirt, which had the insignia of his hip-hop crew Small Change on it: “I put this shit in your brain / You ain’t thinking about $2,000 when your shirt says Small Change.” Jah seized the opening–“I’ma tell the motherfucker right there when I be on it / I’ma show you how to sell T-shirts with me on it.” That sealed the contest.

Sketch’s most difficult win was over Doomsday, a smart MC who opened with a slam on Sketch’s microphone troubles: “Here we go y’all, it’s fight night / I’ve been watching you the whole time, you need to hold the mike right.” But Sketch kept chipping away at him, serving below-the-belt digs at Doomsday’s ethnicity: “Wanna mess with me? I spit a lipful / This what happens when a Puerto Rican fucks a pit bull.” When he was pronounced the winner much of the audience booed.

By the time he faced Jah Safe in the finals, Sketch was sweating. He managed some early zingers about Jah’s size–“Stop talking this shit, you really need some info / So skinny he could slide through a closed window”–but when Sam I Am came back on to beatbox and the format switched to two-bar trade-offs, Sketch began to flail. Jah, in contrast, was unflappable: “Understand when I come through my mike is my weapon / I’m sitting here chillin’, this nigga pipin’ and sweatin’,” he spat out at one point. At another he dissed Sketch’s age: “Telling you, you got no green but you herbing fast / I’ma stick this microphone dead in yo’ virgin ass.” Finally Sketch simply stopped, speechless, and the whole thing was over. “He just hit me at the end with a couple lines where I was like, ‘Damn, how am I going to follow up?'” he says. Jah “was like a cannibal that night.”

Jah Safe got the $2,000 in a briefcase full of bills and a jar containing the 159 wristbands of the losers. But for a guy who couldn’t make it past the door on an ordinary night, Sketch hadn’t done so badly. “When it was all said and done I was happy, even though I didn’t win,” he says. “One guy put it the best: I may not have been the last man standing, but I was the last to fall. And that in itself was an honor.”

Art accompanying story in printed newspaper (not available in this archive): photos/Barry Brecheisen, Oscar Contreras.