Home / Music / Music Feature / oddCouple Bridges the Distance Between Chicago's and Milwaukee's Rap Scenes

oddCouple Bridges the Distance Between Chicago's and Milwaukee's Rap Scenes

Jun. 27, 2017
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oddCouple performs at 7 p.m. on Tuesday, July 4 at Summerfest's Briggs & Stratton Big Backyard stage.

Rappers tend to portray themselves as the masters of their own fates, chalking up whatever success they achieve to their own talent and hard work. Zach Henderson, who records and produces under the moniker oddCouple, isn’t ashamed to admit there was more than a little luck involved in his own rise, though. If Henderson hadn’t moved to Chicago for college when he did, and hadn’t fallen in with the crowd he did—including rapper Alex Wiley and Chance The Rapper’s manager Pat Corcoran—he wouldn’t have been in the position he is today.

In 2007, when Henderson relocated to the city from Milwaukee, Chicago’s rap scene was on the brink of a rebuild. While Chicago luminaries like Kanye West, Common and Lupe Fiasco were all near the peak of their careers, a younger generation of rappers and producers were in the earliest stages of developing new ways to approach city’s tradition of soulful hip-hop.

It would take years for those seeds to begin to bear fruit and for those artists to build a community, but Henderson needed that time himself. He describes his early beats as proficient but nothing special. “I started playing my beats for Chance and Alex Wiley and all those guys, and they thought they were cool, but it wasn’t like they responded, ‘Oh my god, we’re gonna make a legacy,’” Henderson says. “It was good music, though, and I just kept working at it, and over time I got better at it.”

Eventually, Henderson was getting placements on Alex Wiley’s mixtapes and turning heads with a track he produced for Chance, “Burn the City.” In the years since, of course, Chance grew from a regional star into a bona fide star, a Grammy-winning, festival-headlining icon who increasingly looks like one of the most influential rappers alive, and his success has helped lift the whole city.

“To be part of something special like this new Chicago renaissance, there’s a lot of luck involved,” Henderson says, noting that he’s especially lucky, given how most of the artists in his scene are lifelong Chicagoans who have known each other since they were kids. After a decade in Chicago, though, he speaks about the city like he’s a native.

“A lot of Chicago’s greatest songs are homages to pain and coming out of it stronger,” he explains. “That’s what made Kanye so accessible to people. That’s what made Common and Lupe so accessible, and that’s what powers this sound, and anybody who is a true Chicagoan can relate to that. That’s why I always identified with Chicago. You know, Chicago toughens you. You live here and your skin gets harder, but at the same time you never lose your heart. Chicago is like a single mom. It’s the toughest situation, but at the same time you end up growing to love your kid that much more because of everything you go through together.”

At the same time, he’s kept a foot in Milwaukee as well. He returns here regularly (“I live for the weekends when I get to come up and hang around Brady Street or run down Prospect,” he says), and he’s kept tabs on Milwaukee’s own ascendant rap scene. Both of his oddCouple albums, including last year’s Liberation, are packed with Chicago guests like Jamila Woods, Kweku Collins, Mick Jenkins and Saba, but they’ve also spotlighted Milwaukee talent like WebsterX and Siren.

It’s in that spirit of bridging the distance between the two city’s music scenes that Henderson has helped curate a showcase of talent from both cities at Summerfest billed as the Lakeside 4cast Festival on Tuesday, July 4 at Summerfest’s Briggs & Stratton stage. oddCouple will perform, along with Milwaukeeans IshDARR and WebsterX and Chicagoans Joey Purp, Saba and the night’s headliner, Jamila Woods, whose gorgeous 2016 album, HEAVN, Henderson executed produced.

As Henderson sees it, Milwaukee and Chicago have more in common than they realize. “There’s a joke in Chicago that Milwaukee is Chicago’s biggest suburb, but I’ve always felt like Milwaukee is Chicago’s cousin,” he says. “They have the same last name and the same lineage; they were just brought up by different people. There are so many parallels between the two; the lake being one of them. What Lake Michigan symbolizes to people is different from what an ocean symbolizes, and it’s different from what a river symbolizes. It’s family, it’s coming together—it’s those days you get to go out to the lake with the family and hang out. Those are the days you wait for all year. I think the cities are starting to realize that shared connection, which is why there’s been so much collaboration between the two cities in the past year. I’m really happy to be leading that charge.”

oddCouple performs at 7 p.m. on Tuesday, July 4 at Summerfest’s Briggs & Stratton Big Backyard stage.

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