Rhymefest at Exclusively Yours Auto Spa, October 21
Rhymefest at Exclusively Yours Auto Spa, October 21 Credit: Marc Monaghan

State Street between 58th and 59th isn’t in the best shape. Empty buildings and empty lots dominate the block, and the cracked, faded asphalt makes it pretty clear that the Department of Transportation doesn’t consider maintaining this particular street a high priority.

Last Thursday morning, Exclusively Yours Auto Spa (“Shouldn’t Your Car Be as Exclusive as You?”) stood out from the rest of the strip simply because it was obviously occupied by humans. The bay doors were rolled up, letting in the early autumn chill, and a crowd of 30 or 40 reporters, photographers, TV cameramen, and neighborhood folks milled around inside. Che Smith—a third-generation resident of the 20th Ward, which includes parts of Englewood, Back of the Yards, and Woodlawn, among other neighborhoods—was making his first public appearance since announcing he was running for City Council. If there was a bigger media turnout than you might expect for a guy who’s never held or even run for office, it was because Smith, 33, is better known as rapper Rhymefest, who won a Grammy for cowriting Kanye West’s “Jesus Walks.”

It was probably the first Chicago aldermanic announcement to make headlines on Pitchfork and the blog of hip-hop magazine XXL, and several music writers had turned out alongside the political bloggers, neighborhood newspaper reporters, and TV news crews.

Smith’s celebrity is a double-edged sword in this context, though. Incumbent 20th Ward alderman Willie Cochran, a former Chicago cop backed by City Hall insider and key Daley ally Leon Finney Jr.—cofounder longtime president of the social-services nonprofit the Woodlawn Organization and still CEO of its private real-estate arm, the Woodlawn Community Development Corporation—knows that rappers aren’t usually seen as selfless public servants, even in overwhelmingly black communities like the 20th Ward. In a Sun-Times interview published the same day as Smith’s press conference, Cochran called him a “known hip-hop artist who degrades women and promotes violence in his videos.”

Anyone who’s heard Smith’s music knows he’s aesthetically and ideologically miles away from gangsta rap. I’m pretty sure I’ve seen every one of his videos, and I haven’t spotted a single booty dancer. After UK prime minister David Cameron, at the time an MP, decried hip-hop for inciting violence, Smith arranged a meeting with him to advocate for its socially conscious side. But even if this “known hip-hop artist” can convince voters he’s not a thug, he still has to persuade them he’s more than a naive celebrity running to flatter his vanity.

Smith’s campaign, organized with the help of political consulting firm Kurth Lampe, is handling the issue carefully. A press release distributed at the event foregrounds Smith’s recording career and includes a bland but glowing endorsement from Kanye, who praises him as “dedicated to improving the community he grew up in.” But it also plays up his activism: he’s volunteered for the Woodlawn Organization, the nonprofit tutoring and mentoring group Cabrini Connections, and the Happiness Club, which helps troubled and at-risk youth by getting them involved in the writing, performing, and recording of music. (Maureen Schulman, board president of the Happiness Club, says Smith is stepping up his involvement in 2011 and plans to bring some of the kids to town hall meetings.) Plus of course it mentions Smith’s meeting with Cameron (leaving out the part when he invited the MP to go clubbing) and his contacts in the U.S. House of Representatives—last year Smith testified before Congress on the subject of the Performance Rights Act, which would provide artists with royalties for terrestrial radio play, and in the process met with Michigan rep John Conyers (the bill’s author), Texas rep Sheila Jackson Lee, and Georgia rep Hank Johnson.

Everything about Smith’s campaign points to an attempt to find a balance between fight-the-power MC and serious politician. He’s running under the name Che “Rhymefest” Smith, and his campaign poster looks like a cross between a typical political design (prominent Chicago stars, conservative sans serif font) and something you’d see taped to a streetlight on the south side to promote a rap record.

The one question Smith probably can’t answer credibly is how capable he is—in that, he has a lot in common with most first-time aspirants to office. The shape of his rap career demonstrates his commitment to principle, though: With help from Kanye and wunderkind producer Mark Ronson, he landed a major-label deal, then used that position to put out music that promoted a staunchly working-class ethic diametrically opposed to the insanely lucrative gangsta-rap paradigm. After the release of his first proper album, 2006’s Blue Collar, he ended up in a protracted battle of wills with his label, and his long-delayed follow-up, El Che, finally came out this June on the small indie dNBe Entertainment.

At the auto spa he seemed determined to reach an audience that doesn’t know or care what he’s done in music. He looked every bit the campaigning politician, dressed in a suit and vest in front of a huddle of local business owners and family members—including his grandma and his children, two-year-old Amirah and 12-year-old Solomon. He even posed holding babies for news photographers. Speaking in front of cameras and reporters isn’t quite the same thing as being onstage, of course, and I thought I picked up a little nervousness. But he stayed on message. “We don’t have to reinvent the wheel. We just have to reinstate it,” he repeated. Entrepreneurship and community organization are essential to the 20th Ward’s revitalization, he said. He talked about getting rid of red tape that entangles homeowners and stifles small businesses, returning more than once to the idea that people needed to be able to easily buy abandoned property adjacent to their own.

The day after Smith’s press conference, Andrew Barber of Fake Shore Drive, the most influential locally focused hip-hop blog in Chicago, responded incredulously to the flood of coverage: “Has an Alderman EVER gotten this much press?” Well, sure. Willie Cochran’s predecessor as 20th Ward alderman, Arenda Troutman, got a lot of it when accusations that she’d taken bribes derailed her campaign and handed the 2007 election to Cochran—and she got more in 2008, when she went to jail for mail and tax fraud. But it is possible that no mere candidate for alderman has ever come out of left field and attracted so much attention so quickly. Smith’s task is to turn that attention into enough votes to beat Cochran and any other challengers who may arise. The application deadline isn’t till November 15, but candidates need to collect just 143 signatures to get on the ballot—2 percent of the ward’s turnout for the 2007 aldermanic election, which in the 20th Ward was 7,134. (That might sound low, but only a third of all wards cracked 10,000 that year.) One fellow first-time office seeker, George Davis—a sales executive for his father’s finance company, a block-club vice president, and a member of the steering committee of the Woodlawn Neighbors Association—passed out campaign fliers at Exclusively Yours after Smith finished speaking.

Once he was through on the mike, Smith took questions from the scrum of journalists gathered around him and posed for pictures with fans and neighbors. One guy pressed a burned demo CD into his hands. Since Chicago politics has an even worse reputation for ruthlessness and corruption than the music industry, I asked Smith what he’d learned as a rapper that he could apply to his new endeavor. “Numbers matter,” he replied. “Numbers matter, and with music you have to engage the audience. With this we’re going to engage the community. That’s what you have to do.”