Rhymefest in 2014 Credit: Chandler West/For Sun-Times Media

Che “Rhymefest” Smith didn’t set out to perform at the Chicago Blues Festival. When Frayne Lewis, a programmer with the Department of Cultural Affairs and Special Events, approached the rapper last fall, it was to brainstorm ideas to shake the festival up. “The Blues Fest was not evolving. It wasn’t evolving as you see Lollapalooza evolving,” Smith says. “I suggested connecting [with] Donda’s House—the organization that I’m a part of that does artist development for youth—[to help] young people reimagine the blues.” In February DCASE, Donda’s House, and AARP launched a program called Bridges to the Blues, which invites young musicians from various genres to collaborate with older players and compete for a chance to perform at the Blues Festival. His work on the program inspired Smith too: “When I saw how that was turning out, I was like, ‘Well hell, I wanna perform too!'”

Smith isn’t just a pillar in the Chicago hip-hop community—he’s also an educator and a former aldermanic candidate (he ran in 2011). He cares deeply about finding ways to connect the city’s black cultural legacy to the people who can carry it into the future, and for that reason he’s unconcerned about whether his Blues Fest appearance will ruffle the feathers of musical purists. He’s recently butted heads over hip-hop with veteran blues harmonica player Billy Branch, whose set follows his on Friday night at Pritzker Pavilion. “Every time Billy and I get together, he doesn’t waste a moment to tell me how he doesn’t like hip-hop,” Smith says with a laugh. “So you find these challenges of ‘Well, music should be like this!’ and ‘Music should be like that!’ But conquering that and having those conversations are important to the evolution of music.”

Smith recently began working with Branch on a remix of “Help Me,” a languid, smoky number the harpist recorded with guitarist Lurrie Bell for the 1982 album Chicago’s Young Blues Generation. “I’m making that specifically for the Blues Fest,” Smith says—and Branch will join him onstage.

The remix is part of a shift in Smith’s approach to recording and releasing music. In 2014 he launched a PledgeMusic page for his upcoming third solo album, Violence Is Sexy, a project he soon abandoned—he says he’s done making albums. (He also says that because he didn’t finish the record, the pledges never became donations.) He made the decision after writing “Glory” with Common and John Legend for Ava DuVernay’s 2014 Martin Luther King Jr. biopic Selma.

Selma went to the Oscars, and it gave me an epiphany—that music has to be connected to something productive,” Smith says. “There’s so much music. Music is for free. You can get it on Spotify for free. So what, I’m gonna spend $15,000 to create an album that people are gonna get for free, play for a week, and it’s over? No, music should be connected to movements. So any music that you hear from me from now on is gonna be connected to something tangible.” Recently he recorded material for The Public, a forthcoming film by Emilio Estevez about a standoff between police and library employees. Smith also acts in the movie, playing what he calls “a homeless gentle giant” who gets caught up in the library occupation.

Working on tracks specifically for Blues Fest is an extension of Smith’s new approach. “I don’t believe that most artists—especially hip-hop artists—that you see today are making their money off music. They’re making their money off products,” he says. “I just want my product to be community. The Blues Fest—you’ll hear new songs that I worked on with Jazzy Jeff, and stuff strictly for this show. I want my music to be connected with who I am as a person and my movement in the community, not just for the sake of my ego.”

Smith wants to keep the blues—not just the Blues Festival—alive and relevant for future generations. “We have to start training each other to replace ourselves,” he says. “I think that’s not only been an issue with the Blues Fest, but the issue with many of our institutions—political, social, and arts-wise—in Chicago.” Foregrounding connections between the blues and hip-hop, he explains, could be a way to bring young blood to the old genre.

In Smith’s view, hip-hop and the blues share core values. “Hip-hop, at its essence, tells stories—stories about revolution, about community, about hopes and dreams,” he says. “Blues comes from that same type of struggle.” His arguments about music with Branch are like sibling squabbles, where closeness magnifies small conflicts. “I believe that one of the reasons Billy Branch and I debate hip-hop and its messages and the blues so much is because it’s so much alike,” Smith says. “It’s the same thing, like, with a different drum pattern.”

Rhymefest performs on Friday, June 9, at 6:20 PM at Jay Pritzker Pavilion.