Credit: Todd Diederich

You’ve probably seen Jimmy Whispers‘s street art around town. Since spring 2012 he’s been pasting up his crude and blocky cartoonlike drawings, which usually involve one or all of the following: a handgun, the Chicago Bulls logo, a pot leaf, an ice cream cone, a shark, and the phrase “Summer in Pain.” He’s also a musician, though you might not know it unless you’ve happened to see one of his shows—he hasn’t released anything, and unless you count two Chic-a-Go-Go clips, none of his lo-fi pop songs are online.

His songs, unlike his street art, have a clear message: they’re about love, the kind that can overcome misery and brutality. In fact, the Summer in Pain Festival he’s organized this weekend at the Hideout benefits Chicago-based violence-prevention group CeaseFire (known nationally as Cure Violence). I learn one reason this might be important to him shortly after we walk into Marble in Logan Square for an interview: as he bites into the wedge of lime that came in his gin and tonic, I hear a small crack, and he reaches into his mouth to pull out a broken temporary tooth. He sticks it in his pants pocket.

This is how he comes to tell me the story that in late February he was assaulted by “some white kids” while walking home drunk from a friend’s place on a side street near the 14th District police station in Logan Square. He says he got jumped and kicked in the mouth; he lost one tooth, another broke in half, and a permanent implant got messed up. Shocked and numb, Jimmy holed up—he didn’t even report the attack. “I just went into work every morning and came home and drank a lot to keep myself from feeling that pain, ’cause it was, like, exposed nerves and stuff,” he says. Eventually a gig opening for Parenthetical Girls at the Empty Bottle at the end of March forced him out of the house. “I still smiled,” Jimmy says. “But yes, it was terrible.”

Jimmy and his well-loved Thomas Californian electric organCredit: Todd Diederich

Shortly after the attack, Jimmy saw The Interrupters, the 2011 documentary by director Steve James and author Alex Kotlowitz that follows several of CeaseFire’s violence “interrupters” as they try to stop killings in high-risk Chicago neighborhoods. The film struck a chord with Jimmy, whose idealism had already found an outlet in his music. Since summer 2011 he’d been using his iPhone to record airy, accessible love songs animated by his life-affirming vigor and almost childlike sincerity and whimsy; he belts out his lyrics while playing an old multikeyboard Thomas Californian electric organ in his apartment.

Jimmy won’t discuss the cause of the pain in his songs, and the people I spoke to about him either didn’t know or didn’t want to talk about it either. The grain in his singing voice makes it clear he’s struggling with something big, but he won’t get more specific than “I was just in a really bad place.” He recorded without rehearsing and sometimes made up lyrics on the spot, which helps him sound like he means it. “Recording things this way, that feeling of the moment is alive,” he says. “It doesn’t get deadened after a while.”

Jimmy has had his debut album in the can for more than two years, but he’s held off on releasing it—he’s looking for the right label. He’s also deliberately keeping his music off the Internet. “Everybody’s mom and dad is on Bandcamp,” he says. “Anyone can do it, so there’s nothing special about it.”

That’s not to say he doesn’t self-promote. In summer 2012 he published a zine, also called Summer in Pain, that includes a collage about Chicago’s gun violence, plenty of sharks, and a “psalm” about a pain that’s so raw it dislocates bones. And he’s got his street art, of course—which is why he’d rather not reveal his real name or talk about his old band. “Jimmy Whispers” is a nickname he says he got as a kid because he was shy.

You can sort of tell that Jimmy wears his “Summer in Pain” T-shirt every day.Credit: Todd Diederich

Jimmy doesn’t just attach the phrase “Summer in Pain” to all his work; he also attaches it to his person, on a white T-shirt he wears literally every day, often with a vintage red Chicago Bulls jacket he’s had since he was in elementary school. (“I was a fat kid,” he says.) It might look like Jimmy is obsessed with pain in a vague, general way, but during our talk at Marble he brings up the September mass shooting in Back of the Yards that injured 13 people. “Stuff like that happens, and I’ll hear it and be in the most somber mood and go home and cry,” he says. “There’s nothing else I can do. I can’t help but think about it.”

A couple months after he saw The Interrupters, Jimmy got in touch with Cure Violence director of development Patricia Broughton to set up a benefit show. Not every request passes muster, but Broughton approved Jimmy’s—she liked the antiviolence content of his street art, and she was persuaded of his bona fides by a loving Gossip Wolf item that my colleague J.R. Nelson wrote last December. “His mission is very much in sync with our mission,” she says.

That benefit show has become the Summer in Pain Festival, which takes over the Hideout on Friday and Saturday nights. On Friday lo-fi pop act Advance Base headlines a bill that also includes Plastic Crimewave Syndicate, Cool Memories, and J Fernandez; on Saturday night Jimmy closes the fest after sets by Chandeliers, Yawn, Mines, and Ono. “He had mentioned that there was gonna be celebrity guest speakers and comedians and jugglers and, like, elephants and tigers, like a circus act or something like that,” says Mines main man Bill Satek. “Who doesn’t want to be involved in something like that?”

Jimmy has told me a little about what he has planned. To kick off Friday’s concert, he and Chic-a-Go-Go cohost Ratso will do a duet of the Drifters’ 1962 classic “Up on the Roof,” which they performed on the TV show earlier this year. The Hideout will be decorated with inflatable sharks and street art, and he’s renting a high school basketball scoreboard. “Instead of ‘home’ and ‘away’ it’s gonna say ‘pain’ and ‘us,'” Jimmy says. “Anytime a band plays, points are gonna go up and the buzzer will go off.”

He’ll play host throughout the weekend, and if his live shows are any indication, you can expect lots of strange banter and borderline frightening enthusiasm. Because Jimmy uses an iPod instead of a backing band, he’s free to cut loose and roam around—he might start doing push-ups or push people together to encourage them to couple up and slow dance to “What a Wonderful World.” He’s confrontational, playful, and sometimes a little disorienting. J Fernandez didn’t know exactly what to make of the first Jimmy Whispers set he saw: “I thought he was going through some weird breakup or something, ’cause he jumped off the stage and went outside with the microphone,” he says. “I was actually kind of worried about him.”

Jimmy Whispers enjoys a dollar corn dog at the Tastee Freez near Armitage and California. On Chic-a-Go-Go he once lip-synched using a corn dog as a microphone.Credit: Todd Diederich

Fortunately, Jimmy’s music keeps the mood light. His songs are so jubilant and catchy that it’s easy to get swept up in the performance. When I first saw him, at the Whistler last December, I noticed Love of Everything’s Bobby Burg singing along to nearly every word. “I loved it instantly,” Burg says.

Jimmy hopes to finally release Summer in Pain next spring—the culmination of all the work he’s done to get his mantra stuck in people’s heads. This weekend’s festival, though, is about more than his own art. “The festival isn’t as much a part of the plan as it’s just trying to reach out to the community and do something good,” he says. Jimmy follows his heart when he records, trying to capture feelings in a way that will move his audience, and with the Summer in Pain fest he’s doing something similar—trying to transform an emotion into a concrete result. “There’s things I can plan,” he says, “but there’s things I’m just having a feeling about and need to react to.”

Jimmy adds some color to Waldheim Cemetery in Forest Park.Credit: Todd Diederich