Born Dwayne Holt, Jr., he adopted the name Illwin at the now-defunct McNally Smith College of Music in Saint Paul, Minnesota. There, enrolled in the hip-hop studies program, he started dropping music on SoundCloud. He also helped his class craft a marketing campaign for General Mills, the multinational manufacturer, during his time at the college. The class won the competition with a song called “Crazy,” which was used as an April Fools theme song for Hamburger Helper. It went viral.
Since then, Illwin moved back to Dayton and has proved to be a dynamic and prolific solo artist. Last year, the juxtaposition of his releases “breakdown” and “BeTTeR DaYS” represents the light and darkness he was struggling with at the time. On the other side of that struggle is the release of his latest singles.
“I just want to enjoy life. I desire partying,” Illwin said. “I desire being around people and feeling energy and eagerness and enthusiasm for life itself. Being fearless, and knowing there’s no rules. I make my own rules, and I deserve to be here just as much as anybody else. I can take up space.”
The rapper grew up on Busta Rhymes, Beyoncé, and James Brown; those influences stand out in his loud showmanship. In terms of rap style, Jay-Z and Missy Elliot come to mind, and so does Kanye West, particularly his album, “My Beautiful Dark Twisted Fantasy” — though, as Illwin puts it cordially, “not so much these days.”
He’s also studied a lot of Ohio funk musicians, like the Ohio Players, Bootsy Collins, and George Clinton, and often borrows their swagger and style while referencing them in his act.
During Week 3 of this year’s Dayton Battle of the Bands, Illwin put on a compelling and choreographed show for the Hip-Hop / Rap / R&B night. It was clear that his “no rules” philosophy permeated the performance by offering something different. Joined by two masked dancers, à la “The Phantom of the Opera” meets modern dance, and a backline DJ, à la Mix Master Mike, Illwin went full performance art in lieu of straight rap. Wearing a bawdy cape, as if dressing for the job he wants, Illwin took first prize in the category.
It was a bit of histrionic rap that was pure entertainment, a type of show that made the audience wish they had a few more eyes just to see everything happening on stage.
“I wanted to become a character,” Illwin said. “That’s why every time I perform, I look like a character.”
Arianna Holiday, singer and “Dayton’s Sassy Sweetheart,” joined Illwin for the song “BeTTeR DaYS.” Holiday passed out glow stick bracelets to the crowd prior to the set. While it wasn’t clear why, aside from the obvious being they lit up the room, it was just as memorable a gesture as the trophy-winning performance — so much so that mine is still in the freezer.
Illwin said that Holiday, who provided intermittent background vocals to the song, “really represents what ‘BeTTeR DaYS’ is about.” As a brain tumor survivor, she also procured a lust for life after almost losing hers. When she picked up the singing bug a few years back, one of Holiday’s performances — which featured outfit changes — caught Illwin’s attention. They’ve been collaborating ever since, with their latest being on the 2025 track, “My Life.”
Illwin says when he puts on another show, it will be a step up from what he’s done before. He believes he’s going to call his next project “Fearlessly in Lust.” While “lust” may have a certain connotation, he says that it’s not a sexual thing at all, rather “it’s about celebrating life and all my desires and being fearless.”
He makes his own rules, and breaks the ones that are there. It’s his choice, his voice. All they do is make noise.
Illwin’s “Mr. Get Stupid Wit It” and “My Life” were available on all streaming platforms May 30.
Brandon Berry writes about the Dayton and Southwest Ohio music and art scene. Have a story idea for him? Email branberry100@gmail.com.
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