For years if you asked any career-minded Milwaukee rapper about their ultimate ambition, they’d almost inevitably offer the same response: They wanted to be the first rapper to put Milwaukee on the map. Few, however, seemed to appreciate what a tall order that was. Save for a brief window when Coo Coo Cal’s one hit “My Projects” briefly topped the national charts, Milwaukee rap has always been a scene not only without a star, but without an identity. Every year local rappers made valiant efforts to move the needle, to shake the scene from its decades-long rut, but in the end none came close.
They were going about it wrong. As the city should have learned when Coo Coo Cal came and went, one rapper alone can’t put an entire city on the map. It takes a community of artists to grow a national reputation, and for perhaps the first time in its entire history, Milwaukee’s rap scene has the talent to make that happen. A young new generation of rappers, some of them working in concert with each other, others operating as lone wolves, has injected real excitement and vitality into the scene and outsiders are beginning to take notice.
Some of these rappers have been highlighted by taste-making publications like Complex, Vice and Fader; most have received glowing write-ups from major rap blogs. They’re all attracting listeners from beyond the city and at least a couple of them have real star potential. The odds are still stacked against them, of course. A few if not most of these artists will disappear without having made the mark they’d hoped to, because that’s how it works—rap is cutthroat and unsentimental, always primed to move on to the next thing. But for the time being, they’re all making some magnificent music. Meet 11 rappers who are anchoring a rap scene that’s stronger than it’s ever been.
Klassik
Age: 26
Signature Project: The album In The Making
Sounds Like: A jazz kid raised on Stevie Wonder, Steely Dan and hip-hop
The Background: More than any rapper on this list, rapper/singer/producer/songwriter Klassik has assumed a leadership role in the scene, producing for and mentoring others artists. “I may not be the best rapper or piano player or singer,” he says, “but I think in this scene my role is that of an impassioned performer and creator who’s done my part to continue to inspire others so that it can continue to grow.”
WebsterX
Age: 22
Signature Project: The video and single “Doomsday”
Sounds Like: Experimental rap, minus any stigma associated with that term
The Background: WebsterX doesn’t rap so much as he chews words into a sticky pulp, and that delivery is complemented by his ear for dreamy, effervescent production—a combination that caught the attention of seemingly every worthwhile rap blog this winter with his single “Doomsday.” Like many of his peers, WebsterX views coming from Milwaukee’s undefined rap scene not as a burden, but as opportunity. “It’s fun to be from a place that hasn’t had much success as far as hip-hop goes,” he says. “We’re the young pioneers; we must take advantage of that and do it right.”
Bliss & Alice
Age: 22
Signature Project: His mixtape Poetry Vol. 1: The Shit Talker Tape
Sounds Like: Allen Ginsburg by way of Earl Sweatshirt
The Background: Bliss & Alice (yes, he’s just one person) takes his primary cues not from rap, but from beat poetry and spoken word, spinning dense webs of prose about addiction, resolve and madness. His breakthrough mixtape Poetry Vol. 1 piles one head-turner on top of another, many of them at once chillingly dark and cathartically funny, and all of them lacquered with incredible wordplay. He’s a prodigy, plain and simple.
IshDARR
Age: 18
Signature Project: His album Old Soul, Young Spirit
Sounds Like: Lupe Fiasco’s feisty little brother
The Background: On his earliest tracks, recorded while he was still in high school, IshDARR demonstrated he could spit with supreme dexterity and charisma, and his work has only gotten better as he’s loosened up. Old Soul, Young Spirit finds the sharp-tongued freshman shifting away from conscious rap ever so slightly in favor of limber party rap tailor made for college campuses.
Reggie Bonds
Age: 23
Signature Project: His 2014 mixtape The Miseducation
Sounds Like: A ’90s hip-hop enthusiast with a wild streak
The Background: If there’s one trait that unites all the artists on this list, it’s open-mindedness. None of these rappers are wed to just one style or strain of rap, and that’s especially true of Reggie Bonds, whose primary fascination is issue-driven hip-hop but who isn’t afraid to detour into rowdier sounds or boisterous trap music. When he takes the gloves off, as on his Molotov-cocktail-lobbing new single “Menace II Society (Black Timbs),” the results are kinetic.
Yo-Dot
Age: 30
Signature Project: The album Red Mist
Sounds Like: A grizzled hard-head with a soft heart
The Background: The oldest artist on this list, Yo-Dot came up with an earlier generation of Milwaukee rap, alongside Prophetic as part of the Umbrella Music Group, one of the more prominent local rap crews of the late ’00s. But he’s been doing his best, most thoughtful work in recent years, recording albums that bracket his white-knuckled persona with rich, gorgeous production.
Milo
Age: 23
Signature Project: His 2014 album a toothpaste suburb
Sounds Like: A Rorschach inkblot spreading in real time
The Background: There are rappers who color outside the lines, then there are rappers who refuse to acknowledge lines altogether. Over lo-fi beats that unfold with the logic of M.C. Escher drawings, Milo rhymes in free-association streams of thought about culture, identity, existence and punctuation, or whatever else crosses his mind. He’s a bit of a nomad, having done time in several other cities, including Los Angeles, where he joined the rap collaborative Hellfyre Club, but life always seems to return him to Milwaukee.
El-Shareef
Age: 21
Signature Project: His mixtape Retrospective 2: Freeworld
Sounds Like: Hip-hop in the Internet age
The Background: Like quite a few artists on this list, El-Shareef revels in the anything-goes aesthetic of contemporary independent hip-hop, drawing from a hodgepodge of influences ranging from Top Dawg Entertainment’s cloudy conscious rap to ’90s boom-bap and Houston screw music. It’s inventive music that’s always in motion, always keeping you on your toes.
Pizzle
Age: 27
Signature Project: His upcoming album Grand Design
Sounds Like: The very pulse of what’s popular in rap right now
The Background: Since tasting local radio play a few years ago with the Packers anthem “Green and Yellow,” perhaps no Milwaukee rapper has worked harder to break big than Pizzle. He regularly collaborates with proven hitmakers like Jahlil Beats, Cardo and Honorable C Note—who collectively have produced for stars like Meek Mill, Wiz Khalifa and Young Thug—but his concise delivery harkens back to an earlier era of hip-hop. “I came up listening to rap when quotables and flow were everything and I think that shows in my music,” he says.
Lorde Fredd33
Age: 22
Signature Project: The album 33: The Education
Sounds Like: Heaven and hell colliding
The Background: This first thing you notice about Lorde Fredd33 is his voice, which is so deep he sometimes sounds as if he’s rapping from another room, behind a wall that’s absorbed everything but the rumble. It’s a remarkable instrument, and he uses it to great effect on this year’s adventurous 33: The Education, which juxtaposes his booming croak against cerebral electronica and clouds of jazz.
Vonny Del Fresco
Age: 21
Signature Project: His just-released album Memoirs
Sounds Like: A comfortable pair of sneakers
The background: Some rappers adopt personas they develop and recalibrate over time. Vonny Del Fresco prefers a more come-as-you-are approach, rhyming with a casualness that sometimes undersells how sophisticated his wordplay can be—of how fiercely he can tear into a track when the beat calls for it. He sees himself as a complement to his peers on this list. “We all have something to offer and have our own lane—none of us sound the same,” he says. “The best part about being a Milwaukee rapper is that I’m able to be a part of the city’s growth and success in the industry. The love and support that I get from this city is a wonderful feeling.”
We've compiled a playlist of some recent tracks from these artists, which you can stream below.
