Longboi

He started making music after the death of a friend, and that pain is still present in everything he creates. His sound is direct, experimental, and slightly uncomfortable—the kind of chaos you’d normally hear on American underground tapes, but which he’s now trying to bring to the Netherlands.

From Tilly to Milwaukee is a four-track EP that doesn’t stand out with hits or radio-friendly hooks. No, this release is an attempt to bring an unfamiliar style—the Milwaukee sound—to Tilburg. To most Dutch listeners, it sounds like pure abracadabra: glitchy, unpredictable, beats that sometimes seem to stumble, and flows that drag you out of your comfort zone. Milwaukee was never a hip-hop hotspot, more like a faint star lingering on the edges of Midwestern rap powerhouses like Chicago and Detroit. But sometimes being overlooked is exactly what makes you strong. That feeling of being an outsider, that underdog energy—that’s exactly what draws Longboi in.

The hip-hop culture in Milwaukee emerged in the ’80s and ’90s, when local DJs, MCs, and dance crews put on small shows in community centers and clubs. Because Milwaukee was often overshadowed by Chicago, the city had to carve out its own identity. That happened through raw lyrics about the harsh realities of city life; poverty, unemployment, violence, and inequality were (and still are) central themes in the music. In recent years, new artists and collectives have pushed the Milwaukee sound further. Rappers like Lakeyah (who later signed with Quality Control in Atlanta), but also names like MT Twins, Lil Chicken, Big Wan, and Chicken P are often mentioned as the city’s flagbearers.

Longboi himself found inspiration in that unpolished Milwaukee scene. Names like Pablo Skywalkin, BIZ, 414bigfrank, and Bristackz showed him that rap doesn’t have to be tight or perfect—it can be raw and honest. These Milwaukee rappers taught him that rap doesn’t need to sound pretty to hit hard. In fact, the rougher the edges, the more truthful the emotion. That DIY attitude, that outsider vibe, is what he carried into his own music: a blend of Brabant’s down-to-earth mentality with the bold Midwest sound. Tilburg isn’t Milwaukee, but kids grow up there with the same feeling of being skipped over by the world. Longboi saw how the big cities take all the shine, and figured out he’d have to find his own way to be heard. That’s the foundation he stands on. He takes the rawness of BIZ, the chaotic energy of 414bigfrank, the street logic of Bristackz, and throws his own Brabant twist on top. No Midwestern accent, but the same fuck-the-rules mentality. Not an attempt to make it neat, but the drive to be heard—no matter the cost.

The EP opens on a lighter note with “WHAT'S HAPPENING (feat. Kurtschen).” It’s a cheerful track full of good vibes, playful punchlines, and even a few small life lessons. Here Longboi shows that he’s capable of more than just chaos: he can keep things light and catchy without losing himself. With lines like “everything you can do, I am better in,” Longboi immediately plants his flag. It’s not a throwaway brag, it’s a statement. This isn’t a kid waiting in the wings for someone to call him on stage—this is someone who just grabs the mic himself and forces the room to listen. His newly woven flow, balancing Milwaukee’s chaos and Tilburg’s bluntness, comes alive here: unpolished, unpredictable, but above all, bone-deep confident.

“BAD” flips the mood completely. A dark, heavy American beat. Here Longboi raps about opportunists—the people who only want something from you once they see you climbing up. The track sounds sharp, biting, and you can feel the frustration underneath. This is Longboi with his knives out. He mixes English and Dutch like it’s second nature. “Shawty know she bad, she wanna fuck with the lights on” drops in casually, almost as a sneer at everyone trying to follow him but failing to keep up. He doesn’t brag about things he hasn’t lived. Every word, every adlib feels like it comes from a smoke-filled room, where the walls are listening and the floor shakes with bass. What makes this track so powerful is that Longboi isn’t just showing rage—he’s showing control. He knows exactly what’s going on: the people standing at your side now weren’t there before. That feeling of betrayal, that mix of arrogance and frustration, gets amplified by the unique beat. His delivery leaves space to breathe. You feel like he could explode any second—but he chooses instead to let you slowly feel just how dangerous that energy is.

Then comes “All Night (ft. DamnDanny),” produced by none other than DamnDanny, one of the pioneers of the Milwaukee sound. It’s the most self-assured track on the record: Longboi raps about women, sex, and his journey as an artist. The flow feels bigger than Tilburg itself. His bars are endless—more bars than a prison—and he drags them along as proof that he can handle anything. “Kan niet slapen tot de opp gevangen is” (“Can’t sleep until the opp is locked up”) rings out like a mantra, an inside view of the hustle he’s living. And then that bar: “Ik weet niet eens wat ik doe, maar doe het right.” (“I don’t even know what I’m doing, but I do it right.”) A perfect summary of his style: improvisation with precision, chaos with control, flawless in a way only Longboi can pull off.

The closer, “Who tf this? (ft. Braydyn & DamnDanny),” is the most experimental cut. Longboi flips between humor and aggression—just because he can. Braydyn, the American artist who first introduced him to the Milwaukee sound, leaves his own stamp, while DamnDanny delivers yet another jagged, unpredictable production. The result is a collision of worlds: Tilly meets Milwaukee, chaos meets flow.

From Tilly to Milwaukee is short, raw, and uncompromising. It’s not an EP for everyone—and that’s exactly the point. Where some records try to impress from start to finish, Longboi takes you on an experiment first, forces you to get used to the chaos, and only then lets it all fall into place. The EP feels short but explosive, like a statement. Longboi makes it clear he’s not just trying to join the Dutch scene—he’s building a new one. He wants something strange, something new, and he’s willing to push it far. Tilburg isn’t the kind of city where you’d expect a groundbreaking underground to rise up, but that makes the title From Tilly to Milwaukee hit even harder. It’s a bridge between a Dutch city and an American niche scene that nobody here really knows.

It would be easy to say Milwaukee rap will never blow up here. Too weird, too uncomfortable, not playlist-friendly enough. But that’s not the point. The point is that someone like Longboi shows that experimentation is still alive in the Netherlands—that there are artists willing to look beyond the rigid frame of what a “hit” is supposed to be. And that makes him a pioneer. Maybe small in listener numbers, but huge in meaning.