Inside the Unmistakable Madness of Milwaukee’s Rap Scene

By Alphonse Pierre

Milwaukee’s rap scene is its own universe, with its own stars, sound, and frequency. Forever undersung, even among mid-sized rap locales like Detroit and St. Louis, the artists in Wisconsin’s biggest city embrace their limited resources, creating distinctive styles laced with fat basslines, drums that rumble like old steam locomotives, funky synthesizers, and too many handclaps to count; elastic Auto-Tune melodies and spice-talking raps; and dances not to be attempted by those with bad knees. The scene is proudly insular, fun, and fast-moving—it’s generally unbothered with soundtracking the lives of anyone outside of Milwaukee, and not a week goes by nowadays without the release of wildly singular and thrilling music.

The songs can be romantic, wounded, fly, fun, comedic, or just some trap shit, and they’re almost always delivered with a signature flamboyance. Hints of Atlanta trap, Houston gangsta rap, Chicago drill, and Detroit street rap are in the mix, along with the offbeat Southern blues of Baton Rouge and the Bay Area’s chip-on-the-shoulder spirit. But the final result is always unmistakeable Milwaukee madness.

“You really have to be from here to get it,” says Lakeyah, one of only a few Milwaukee rappers signed to a major label, of her city’s sound. “Nobody in the industry understands it, but you can dance to it, you can twerk to it, and we got our own lingo.”

It’s a scene full of outsized personalities who are eccentric without ever trying to be anything but themselves. Certified Trapper, arguably Milwaukee rap’s biggest freak, has become a cult phenomenon over the last few years thanks to an around-the-clock churn of nutty, self-produced bedroom recordings. He’s racked up hundreds of thousands of plays on YouTube and inked a deal with Columbia, though he admits it took a minute for people to dial into his eccentricities. “Motherfuckers was calling me ‘weak,’ because my music is kind of harmful to your ears,” he says. “But now people calling me the ‘coldest weak rapper ever,’ and they can’t stop listening to me.”

In my time roaming around the lively city of 570,000, chopping it up with rappers, producers, videographers, DJs, managers, drug dealers, and comedians about Milwaukee rap’s current moment and how they’re building an ecosystem to sustain it, the underlying tone is both prideful and ambitious. It’s a real rap community. All the moving and shaking is done on-the-fly, and the biggest stars are posted up in the parks and gas station markets like everyone else. Sure, they would love it if a chart-topping rapper faithfully repped their sound. But in their minds, they already have a bottomless pool of hitmakers. They’re just waiting for everyone else to get hip.

On a calm afternoon this spring, MarijuanaXO is passing out tiny baggies of weed like sticks of gum as he shoots the shit with his rap partner Joe Pablo. The 33-year-olds became two of the hottest rappers in the 414 area code with their 2021 mixtape Window Service. The project delivers a melodramatic spin on the vivid, drug-dealing tales of slap music, the dominant Milwaukee street sound since the mid 2010s that’s marked by brash beats and stories of hustling.

They’re sitting in a barely furnished suburban home with plain beige walls and one small love seat, just west of city limits. XO calls the North Side of Milwaukee home, and Pablo is from the East, but they often hang out in the ’burbs because the cops don’t bother them as much out here. In their own neighborhoods, being a local star isn’t always a good thing.

“Motherfuckers used to tell us all we got is white people and farms,” says Pablo, talking about the outside perception of Milwaukee and its scene. XO, who’s wearing a sweater that features multiple images of Dumbo the elephant wearing a pair of Timberlands, chimes in, “But now TikTok, the streets, the jails, and the Milwaukee Bucks got the city turnt up—one of us gon’ bust that door down, like Atlanta did, like Detroit did.”

Nodding along at the plastic folding table where XO and Pablo are holding court is the slick-talking rapper Funny $Money, a scrawny videographer who goes by JuicedUpFilmz, and some friends. As they gossip about Milwaukee hood drama and watch their own music videos, a friend and professional chef named Phil throws down in the kitchen.

Phil soon brings out enough trays of food to cater a family reunion: salmon, filet mignon, ribs, mac and cheese, exotic sodas. XO excitedly gorges and smokes until he’s nearly comatose. Pablo, a hefty dude in a tight white tee, bleary-eyed behind his thick shades, dumps multiple tablespoons of sugar onto his rice. When he realizes everyone is watching him, he throws up his hands and exclaims, “Hey, I’m really a hood nigga!”

After the meal, it’s time to get to work. They want to shoot two music videos tonight. The cameraman keeps asking which songs they want to use, but XO and the others pay him no mind. Everything is off-the cuff. They brainstorm locations and consider who can bring the Goyard bags and other designer accessories. Funny $Money is on his phone trying to lock in a video vixen. After 30 minutes, no decisions are made. Everyone shrugs and splits up, figuring it will come together later.

I head with XO to his mom’s crib on the North Side. In Milwaukee the highway can get you anywhere in about 20 minutes; like in many of the country’s cities, it’s set up so that people can zoom in from the suburbs to downtown without having to engage with Black communities. It’s just one of several factors that contributes to Milwaukee regularly being ranked among America’s most segregated metropolitan areas. The intensity of this segregation has made all Black progress in the city an uphill climb, including in the rap scene.

As we get deeper into the North, XO and Pablo singles can be heard bumping out of car windows. The pair started rapping together when they were in high school in the mid-2000s, getting in lots of trouble along the way—XO was kicked out of five different high schools, finally graduating from his sixth. They’ve lived too many rap lives to count, ultimately becoming hometown heroes in their 30s with 2021’s “My Brother.” The song’s no-budget video, shot mostly in an old, smoke-filled kitchen, now sits at nearly 1.6 million views on YouTube.

On XO’s block, elementary school kids excitedly scream “Hey XO!” and he nods their way. The police are lurking. XO posts up on his mom’s wooden porch and proceeds to get so faded that his words start sounding like gibberish. He calls his mom down to unlock the door. A short Nigerian woman in a nightgown appears and gives us both a hug. She’s in disbelief that I’m asking about her son’s music; she doesn’t seem to be a huge fan herself. “People around here seem to like it,” she shrugs, as XO smiles like a child taking their graduation photo. “I just want him to stay safe.”

They have a brief conversation on the stoop about a potential move to Phoenix. XO wants to stack enough bread to take him and his family out of the heart of the North Side. The cautionary tales of imprisonment and death that run through Milwaukee’s hip-hop history weigh heavily on his mind.

For now, he’s getting by. But there are always complications, roadblocks. XO says club promoters in downtown Milwaukee have blacklisted him and Pablo after a few brawls and shootings outside of their shows, forcing them to find gigs elsewhere. Tonight they’re headed to a recording session in Madison, Wisconsin. Tomorrow they’ll hit Kalamazoo, Michigan for a club walk-through, where they pretty much get paid to smoke, drink, and chill. They have enough juice to support themselves with these appearances in surrounding areas, though not everyone has that luxury. An invitation to play Summerfest, the annual outdoor mega festival that is more important to Milwaukee residents than Coachella, has XO feeling optimistic. “Somebody gon’ finally get that real big deal, I just know it,” he says as the moon comes into view, and parents on the block rush their kids inside.

There aren’t a whole lot of nationwide Milwaukee hip-hop success stories, even though the city has a long history of energetic rap music. In the 1990s, promising MCs like Ice Mone and Mr. Do It to the Death put their local touch on G-Funk but were held back by the city’s underdeveloped scene. In 2004, defending his decision to relocate to Atlanta, Ice Mone said, “There is not a good hip-hop scene here, we have a lot of artists and talent but we don’t have any outlets to be heard.”

When hometown stars did stick around, things didn’t go the way they planned either. Coo Coo Cal is still the first name off the lips of almost everyone I speak to, no matter the age, when they reflect on the city’s brightest hip-hop memories. They speak about him as if he’s a folk hero. The rapper hit No. 1 on Billboard’s Rap Songs chart in 2001 with “My Projects,” a rollicking ode to the hardships and joys of the North Side. It led to a five-album deal with Tommy Boy Records, the storied New York label known for putting out classic records by De La Soul, Queen Latifah, and more. But in the early 2000s, unbeknownst to Coo Coo Cal, Tommy Boy was on the brink of failure. When it quickly collapsed, he found himself in no man’s land. Soon enough, drugs and jail put his rap career on the backburner. In 2019, a documentary of his life was released. It was titled The Rise and Fall of Coo Coo Cal.

The city’s rap scene has undergone countless starts, stops, and rebirths; from the era of Coo Coo Cal and Baby Drew, whose 2003 single “Disco Lady” is a regional landmark, to Bless Team’s 2016 joint “Walk First,” a signature moment in the breakout local popularity of slap music. “Jail held us back for a long time,” says “Walk First” producer Tay Love.

Chicken P is arguably the premier Milwaukee rapper of the last seven years, though a series of drug-related arrests has stymied his momentum over and over again. “The city ain’t so big, once you become a star here you’re larger than life, and the police don’t like that,” the 28-year-old wrote from a Milwaukee-area jail in May. (He was released earlier this month.) With his naturally funny, get-rich-quick raps, Chicken has contributed to a part of a handful of the watershed Milwaukee hip-hop tracks, including 2019’s “Fast Cash Babies,” which has collected 3.4 million YouTube views.

In previous years a setback like the city’s most promising rap star getting caught up in legal purgatory could have sent the whole scene into a downward spiral, but right now it’s so rich with electrifying music that it can survive the hard times. “When a bigger artist goes to jail, it just gives the up-and-comings time to shine,” Chicken adds. “Jail not gon’ stop the growth.”

Still, climbing the rap ranks here is a grind. Many Milwaukee venues are hesitant to book rappers. Meanwhile, streaming checks don’t cut it, and the major labels have yet to really swoop in. Being a full-time Milwaukee rapper is hard work that involves booking out-of-town shows in places like Akron, Ohio and Omaha, Nebraska, as well as playing Sweet 16s and backyard graduation parties, and selling features.

At the same time, this inhospitableness is part of what has kept the insularity of the city so intact. Instead of chasing nationwide fame, soundtracking the region is the point, so a highly collaborative, highly productive environment is necessary. A nonstop churn of bonkers singles, posse cuts, and joint mixtapes is what keeps the scene pushing forward.

This relentless hustle can stir up raw feelings when someone actually does break through beyond the city. Lakeyah, who is signed with the star-making Atlanta label Quality Control, home to Lil Baby and City Girls, is as divisive as local politicians here. Word around the city is that she hasn’t paid homage to her Milwaukee roots, instead opting for an Atlanta-meets-Detroit sound. But what goes unsaid is that there’s some bitterness about a woman getting the deal. “In the industry there is so much female rap thriving, but in the city you had to fight 10 times harder to get on as a Black woman,” Lakeyah says. Even as other rising locals like Lonni Monae and MyaaP gain popularity, it’s easy to see how the competitiveness over scant big opportunities could push women away.

On the ground floor of a nondescript office complex on the western outskirts of Milwaukee—the kind of place where Saul Goodman would set up shop—I meet Munch Lauren. Inside, the room looks like the set of a cable-access talk show, with a mix of cherry-red lounge chairs, IKEA stools, and walls plastered with mixtape covers. Munch is fresh off a club appearance the previous night in Flint, Michigan, and the glow of his lime-green sweatsuit and champagne-tinted Cartier shades hides any sign of a hangover. He speaks so softly that I have to lean in to hear him, which is surprising for someone whose whole thing is bringing debaucherous energy to clubs and parties—when we meet, he’s planning to throw a blowout called Cheek Fest.

Raised on the North Side, he got popping in the early 2010s at local teen clubs, most of which have been shut down in the years since. Munch recorded the handclap-driven bounce and raunchy twerk commands of his breakout self-produced 2011 mixtape Hot Boy Munch in his grandmother’s crib, and its near-whispered vocals are a result of him trying to not disturb her.

The tape proved to be a key touchstone in the evolution of Milwaukee’s sound. It pushed things forward from the high-BPM, dance-oriented style of jack rap—typified by Eastside L Boog and Jakitdown’s 2009 regional hit “How 2 Jack”—to a burgeoning subgenre dubbed lowend, which juiced the tempos even more while pairing them with chilled-out flows and lyrics aimed at getting asses to move. Every Saturday, Munch and his friend Bankhead, who passed away from cancer earlier this year, would pull up to parks like McGovern and Lincoln with a tricked-out van blasting their music, selling CDs for $5. Sometimes they even left high school early to set up outside of other schools, ready with discs to push after the final bell.

In recent years, a new generation has deconstructed the foundational rhythms of Munch’s sound with local anthems like Lilqua 50 and Naz Turnt’s “Catch Up 2” and Myaap and Ke Lo’s “Party Crackin.” Sometimes the approach is stripped-down, other times layered with goofy pop samples, with lyrics that range from fun-loving stunting (their idea of fun is bouncing asses and speeding cars) to dancefloor instructions (the incredibly catchy “Lowend Girl Remix”) to drill-like aggression (the amazingly bizarre “Last Chase”). Many of these songs come with music videos shot at Milwaukee’s sweatiest Airbnbs, with all of the city’s dances in view. At the same time, a lack of safe spaces for young Black kids to gather has made the lowend sound hard to find in local clubs. “Parties is unsafe in Milwaukee, so not everybody doing that anymore,” says Certified Trapper. “I make shit for niggas in their cars. That’s what we do, drive.”

As for Munch, he’s still making music, still on the scene: His summer anthem “Shake It” with cyborgian crooner Mula Mar is one of the most feel-good Milwaukee rap songs of the year. Munch is an anomaly in a city where so many careers have been cut short by jail, violence, chasing out-of-town trends, and bad luck—the rare cross-generational Milwaukee rap star.

He lives a life on the road, cruising around from Atlanta to Phoenix to Vegas to all of the small towns in between, pushing his clap-centric, velvety raps in spots that make their money selling bottles and hookah. What has kept him relevant so long is an undying pride for his city. (If you want to know how real it is, he cried on his couch when the Bucks were eliminated from the playoffs this year.) “People always told me, ‘You can’t make it with the Milwaukee sound,’” he says. “But I just won’t give up on it. Everything else don’t sound like me. I’m from Milwaukee.”

The heart of Milwaukee’s rap scenes lies in its predominantly Black neighborhoods, but in recent years its reach has expanded within the city. Outside of a two-story home on a picturesque block in a white neighborhood on Milwaukee’s East Side, with young families hanging out on their sitcom-green lawns, the rhythm of digitized handclaps faintly wafts through the air. Kids in their early 20s, possibly students at the nearby University of Wisconsin-Milwaukee, head to the back entrance with beers in hand. I hand over $10 and follow them into the sweatbox of a basement, where Sharpie scrawls cover nearly every inch of the wall (“Fuck a troll” is written on the boiler), and the pipes are leaking fluid onto the tightly packed crowd. Nobody seems to care.

The young women who live here look a little bit nervous. They throw punk shows in the basement twice a month, but this is the first time they’re hosting a rap gig. It’s a showcase for Run Along Forever, an exciting collective that includes rappers who make everything from emo-rap to rage to lowend. The headlining artist is AyooLii, a 21-year-old born in Kenya but raised on the rougher edges of the East Side. He started out making internet comedy skits (mostly situational Milwaukee bits), until Certified Trapper and producer ThatGuyEli helped him channel his over-the-top persona into music.

With a background in metal and jazz, Eli makes beats by layering guitars and ambience over lowend’s signature claps and snares. AyooLii, inspired by the cosmic melodies of Duwap Kaine and Chief Keef and the soul cleansing wails of Rod Wave as much as the barking common in his hometown, leans into funny, completely bonkers lyrics. Their bent on the hyper-regional sound has found a following on SoundCloud, YouTube, and TikTok, where you can see kids hitting a finger point dance created by local star RealStasher 50k to upbeat AyooLii songs like “Same.”

In the dank basement, as opener Lake performs a track with GothBoiClique-like croons atop a local bounce recognizable to everyone in the room, a lanky kid wearing a ski mask bobs like a pigeon in the corner, and a pudgy dude in an unbuttoned flannel hits taffy-limbed footwork. It’s the same dance that can be seen in parks and on street corners on the North Side any given afternoon, and in just about every Milwaukee rap video right now—the same one countless TikTokkers from across the country do every day without any knowledge of where it came from.

By the time AyooLii grabs the mic, the room smells like old tuna, and everyone’s clothes have become translucent from all the sweat. His energy is frenetic as he runs through a set of songs that includes what one fan calls the “Milwaukee national anthem”—“Shmackin Town”—as he moshes around with a rainbow-colored knit bucket hat sitting perfectly on top of his head. AyooLii’s brother Maz G is shirtless in the pit, leaping so high that his head almost touches the chipped-away ceiling. AyooLii raps about cooking and selling dope in infinite ways, and the crowd knows all of them by heart—which is especially shocking because his catalog is overwhelmingly vast, in the tradition of fellow online wackos RXK Nephew and Lil B. After the show, kids linger around on the sidewalk and talk about upcoming frat parties.

It’s not only the rappers and producers that make Milwaukee’s scene so dynamic, original, and independent. Videographers (including Teeglazedit, Ray Shot It Productions, Shot By DH, and Rich Nerds Productions), studios, engineers, A&Rs, clothing stores (Unfinished Legacy is a hub), managers, and promoters all play a vital part. One of those linchpins is DJ Jerry, who came up in the 2010s hosting local mixtapes. Around 2016, he started the interview series Mixtape Trappers Radio, which he touts as Milwaukee’s first rap podcast. The show, which now has over 100 episodes, has not only shined a light on Milwaukee rappers across generations but also documented tons of history that was at risk of fading away.

Jerry records in the backroom of a building with a decaying exterior on the North Side. On the walls are posters of Malcolm X, late-’90s hip-hop magazine covers, and an in-studio photo of Big Wan, a barred-out East Side rapper who was shot and killed at 19 in 2021. “He ain’t deserve that,” says Jerry, shaking his head.

SteveDaStoner, a charismatic rapper and dancer who can move his body as if it were made of playdough—despite being built like a retired running back—is today’s podcast guest. He went viral for the absolutely wild Magic Mike-style pin-drop dance he busted out amid classic tough talking in the video for 2018’s “2 Busy,” which sits at over three million YouTube views and is the only Milwaukee rap song I heard on local hip-hop radio while I was in town. (The dance was adopted—or, maybe more accurately, ripped off—by two of the most popular streamers on the internet: IShowSpeed and Adin Ross.)

It’s Cinco De Mayo, so naturally, Steve and his friend, the comedian Big Money, strut into the studio with Don Julio, pouring cups with a heavy hand at noon on a weekday. The interview is mostly Jerry and Steve good-naturedly ribbing each other; you can tell they’ve known each other for years. After the recording wraps up, Steve asks Big Money to shoot a TikTok of him dancing in front of Jerry’s podcast logo. Steve throws a large stack of cash in the air as he goes through the steps, but Big Money doesn’t get the angle right. So Steve picks up every dollar off the ground, one-by-one, so he can try it again. “I hate this part,” he mutters.

It’s the first day of the year that feels like summer, and Jerry wants to take advantage of the sun. He drives us to a nearby corner where 414BigFrank, a popular comedian and rapper in the area, is wearing a sombrero and drinking tequila. He’s chilling with a couple of tipsy guys who are talking about potential Summerfest gigs and trading memories of Certified Trapper, who moved away to Houston earlier this year. They dance on top of cars to their own music, which is filled with lots of lowend handclaps. At one point, Frank gets a little sour when talking about how a larger out-of-town rapper he collaborated with didn’t tag him on Instagram. “That’s the way it goes being from Milwaukee,” he says, wistfully.

A minor spat breaks out when live-wire teenage rapper Èsco, who has a couple of lowend anthems under his belt, unexpectedly arrives, speeding onto the sidewalk and scraping Big Frank’s whip. Frank is boiling now. “Come on, man!” he yells, while everyone tries to calm him down, including a professional jokester named ZebraCakeMann (who is actually carrying a plastic bag full of zebra cakes with him). Èsco laughs it off and mounts a motorized pocket bike that he rides up the sidewalk, as people dive out of the way. Nobody seems fazed by the chaos—except Frank, who stews in the background until a couple of children barely old enough for kindergarten line up to snap photos with him.

I jump back in Jerry’s SUV, and we cruise past shuttered teen clubs and lively frozen custard spots; cops pulling over speeding teenagers and smiling families on their porches; the dead sound of traffic downtown and the thump of Milwaukee’s homegrown rap in the North and East. Jerry is a little stiff when he’s downtown, a feeling he shares with a lot of the Black Milwaukeeans I meet. The idea that the city would rather them stay put in their neighborhoods and leave this space for college students, young professionals, and suburbanites is all but said aloud.

We end up back at Jerry’s studio, where his kids are running around, and his mom, girl, sister, and friends are eating tacos and kicking it. One child pulls on her dad’s leg and asks to jump in his arms. Jerry makes a point of showing me a cover of The Source magazine from 1999 featuring Lil Wayne’s early group, the Hot Boys, pinned to the wall. In the late ’90s, the pioneering labels Cash Money and No Limit turned New Orleans into a rap destination that could no longer be ignored. He admires how they etched their way into hip-hop history doing it their way—forcing the genre’s historical hubs to adapt to their sound and style. He stares at the image with a grin on his face, dreams racing through his head.

Listen to a playlist of 50 Milwaukee rap highlights