Photo by Todd Diederich
On a recent Chicago evening, Jimmy Whispers was standing outside Weegee’s Lounge. He comes to the Logan Square dive often, primarily to play shuffleboard. It’s why he was there. The bar has a 1940s-era charm—board games, swing-jazz music, a wooden armoir converted into a craft-beer cooler—and Whispers, a native Chicagoan, is fond of its bygone charm. "I’m where I should be," he said gazing off, nursing his Old Fashioned. "I’m needed now." Whispers could reasonably be called a musician or a comedian but prefers to dub himself a "song and dance man." Tucked into an ill-fitting beige overcoat and sucking down his eighth cigarette in two hours, he looks like a disheveled kid playing detective. Whispers is on the eve of releasing his long-gestating debut album, Summer in Pain, a collection of ultra lo-fi, shambling, confessional pop songs he’s had in the can for over two years. He’s growing uncomfortable, edgy almost at the prospect of discussing himself in its lead-up. He’s an outsize performer but is often cagey about any discussion of his life or its details. The LP is notable for the fact it was recorded on Whispers’ iPhone’s memo app, lending its carnivalesque organ-pop songs a grainy, voyeuristic aesthetic into his inner workings. "I’m still nobody," he says. "Well, I’m somebody. Why am I selling myself short? I’m somebody everywhere. I matter. My life matters. Dammit."
He chuckles nervously.
The self-taught musician and entertainer, who fashions himself something of a modern-day Andy Kaufman, has built a dedicated following around the city via word-of-mouth and his notorious, wild live shows: He’s been known to stagedive into crowds of a half dozen, onstage he’s confrontational and silly ("Mike WiLL Made It! Maybach Music! DJ Khaled! Jimmy Made It!" he barked between songs at a recent gig opening for Ariel Pink). Like Kaufman, he pairs incredible earnesty and awkward comedy for peak confusion. "I want everyone to be in on the joke," he clarifies. "I don’t want to pull shit over their head and make them feel pranked." He sometimes wears dresses when performing, and has been favoring a bright red, cropped sexy-prom look for the last few months. Sometimes it’s over his clothes, other times there is a reveal; it doesn’t zip more than halfway up his back. "I’m a straight male, but I dunno," he said. "I’m so open to everything. My mom’s seen me play where I’ve worn a dress. My dad… it’s too much for him. They’re super old-school.
"I wore this nail polish to my little sister’s wedding in November," he continued. "And my dad was like, 'What the fuck are you doing? What is this?' And my mom and my sister were laughing. They were like, 'You haven’t noticed him doing this for like a couple years?' He was like, 'Why would you do that?' I was like, 'I like how it makes me feel.'"
Raised in the blue-collar Chicago suburb of Berwyn to a military veteran father and a night-shift nurse mother, Whispers, born James Cicero, was constantly performing as a child. Later, he performed in theater in high school. Most of his energy went into basketball, but his hoop dreams died thanks to a case of late development. "I had too much baby fat on me," he said earlier that afternoon, slinked back on the bed in his Westside apartment, drinking straight vodka and smoking a bowl. "I was a late bloomer."
After dropping out of Northern Illinois University and moving back to Chicago, he began taking writing music more seriously: He’d sometimes pen up to seven songs per day on an inherited Thomas electric organ. Circa 2012, fueled by the escalating violence in Chicago and nursing a longtime poster-hanging job that took him all over the city, Whispers began recording what would become Summer in Pain. He complemented the album with a zine of the same name, ever-present street art and a white T-shirt he wears every day with a rough sketch of a big-toothed shark. It’s Whispers’ emotional pleading on the album, particularly on songs like "Vacation", "Heart Don’t Know" and "Michael, Don’t Cry", a track he wrote for his then-toddler nephew that cuts through the literal static.
"They’re open to interpretation for me," he said of his songs. "I could look at them from so many different angles." The majority of the Summer in Pain tracks "were recorded in a single take," he says. "You’re just walking around singing the song in your head all day. And none of it makes sense. Because I’m fucking crazy. I don’t even know what notes I’m about to play. If I tried it again it would sound phony. There’s this bullshit Catcher in the Rye thought to it all. ‘What is phony and what is real’?"
Still, any public notoriety resulting from his music remains frightening to him. "My goal isn’t to be recognized on the street," he said back inside Weegee’s, gathering his red biscuits for a long-overdue game of shuffleboard. "That shit sucks. It’s bound to happen though if I reach any of my ambitions. But that’s not the goal.
"I just want a nice personal life," he added. "Or to be on 'Saturday Night Live.'"