Music
Meet Myquale, the Red Bull Setlist Rap Booth winner opening for Lil Yachty
Ahead of his opening set for Lil Yachty at Radius Chicago, the Milwaukee-raised rapper reflects on his journey to the Red Bull Setlist stage—and the vision driving what’s next.
Sometimes things just go the way they’re supposed to go. Regardless of the detours, roadblocks, or noise along the way, certain paths are simply predestined—and for Milwaukee native Myquale, that destiny led him straight to the Red Bull Setlist Rap Booth, and in turn, a headlining support slot for Lil Yachty at Radius Chicago on October 24.
The Chicago-based rapper, who moved to the Windy City in 2014, was one of 10 hopefuls handpicked by Lyrical Lemonade from submissions recorded at Red Bull’s mobile Rap Booth, which appeared in neighborhoods throughout Chicago. Participants delivered freestyle verses over beats from local producers for the chance to open for Lil Yachty, who narrowed the 10 standouts to three finalists before turning the decision over to a citywide fan vote.
“I was telling every single person I ran into to vote for me,” Myquale explains. That hands-on approach proved decisive. Whether it was his active campaigning—which expanded all the way to New York while he was away on a creative sabbatical—or the undeniable talent shown in his freestyle, fans rallied behind the lo-fi rapper, ultimately helping him claim the winning spot on the Red Bull Setlist stage. However, the opportunity almost slipped away before it started.
A heads-up from a friend at Classick Studios pointed him toward the competition, but a busy schedule forced Myquale to skip one of Red Bull’s Rap Booth pop-ups on August 1. Seven days later, he found the Rap Booth parked along the South Side’s massive Bud Billiken Parade route—squeezing in his submission just 24 hours before flying out to Japan. In hindsight, that near-miss and brief window to spit his verse felt less like coincidence and more like destiny.
Myquale was in the middle of a month-long stay in Brooklyn when the winning email arrived, triggering a rare emotional release. “It was just a huge relief,” he admits, recalling how he went from disbelief to tears in front of his roommate. “I couldn’t do anything but cry. I would liken it to someone in sports who puts in so much hard work during the season, they finally make it to the finals and then win a championship. It’s a dream come true.”
Myquale's Rap Booth submission earned a spot on the Red Bull Setlist stage
© Courtesy of Myquale
I couldn’t do anything but cry...It’s a dream come true
Among the first people Myquale shared the news with was his 24-year-old brother, who’s currently incarcerated. What started as a funny phone mix-up—his brother jokingly mistook Lil Yachty for Lil Webbie (now simply known as Webbie)—quickly evolved into a passionate back-and-forth freestyle session over the phone. Growing up with uncles holding family ciphers, Hip Hop has always been their shared language. Thankful to be able to pursue music professionally, Myquale carries his brother’s spirit onto every stage—and he has his blessing to do so. “He told me, ‘Bro, run full steam ahead with the opportunity. Make the most out of everything,’” he says, sharing his brother’s endorsement.
Myquale’s journey to becoming a rapper began when he was 14. Realizing he needed an outlet to bring his lyrics to life, a classmate introduced him to beat-making by installing FruityLoops directly onto his laptop and an obsession was born. “I was making beats and writing in class,” Myquale remembers, describing the process as both a cathartic escape and a sudden realization of his true calling. “From that moment on, there was just nothing that I loved more than making music.”
Arriving in Chicago at 18 years old after transferring to DePaul University, Myquale stepped directly into a golden era of independent Hip Hop pioneered by local artists like Chance the Rapper, Mick Jenkins, Noname, and Saba. But his musical palette runs much deeper, built on a foundation of childhood 2Pac tapes, his mother’s love of Erykah Badu, and a bootleg copy of Kanye West’s Late Registration that he bought at a Wisconsin flea market.
From burning CDs in middle school to immersing himself in music by Kendrick Lamar and A Tribe Called Quest, his taste has continually evolved to embrace the genre’s shift. “I feel like every four to five years, music changes,” Myquale says, citing Earl Sweatshirt, MIKE, and Karrahbooo as current inspirations. “My favorite album this year is Karrahbooo's album [NOT DA 2]. Honestly, I think the girls are going crazy right now, and Karrahbooo has just been on repeat. I think she’s hard.”
Myquale recorded his winning freestyle in the Red Bull Rap Booth
© Vejune Sidaugaite
He’s also a Lil Yachty fan—which helps considering he’s about to share a stage with him. For Myquale, Yachty represents a rare multi-hyphenate talent whose creative reach extends far beyond rap into fashion, directing, and pop culture. “Yachty is entering a stratosphere that Snoop Dogg has entered,” he says. “There are people who don’t even realize that Snoop is a rapper, because he’s evolved into this personality. I think that very few artists have that ability, but Yachty is one of them.”
He explains that he’s eager to see how his connection with the headliner unfolds off-stage—hoping their shared affinity for lyricism translates into a lasting creative rapport. “When I won, they told me I was his favorite,” Myquale shares. “So I’ll see if he knows me and if he actually rocks with me. One cool thing about Yachty is he occupies so many different spaces. And being from Atlanta, I know he’s used to being around other lyricists; so maybe I’ll get a verse, maybe I’ll get a cameo in a video, maybe it’ll just be a cool conversation.”
Myquale brings his signature energy to the Red Bull Setlist stage
© Courtesy of Myquale
As Myquale prepares for his Red Bull Setlist stage debut, which also features a lineup that includes the likes of kels!, Thirteendegreezº, BabyTron, and a few special guests, he says he’s ready to show the world exactly who he is. “I want to earn that respect and show them I’m not just a finalist who won,” he asserts. “I’m Myquale.” The way he’s going to achieve that is through an explosive set packed with “crazy visuals” and a lot of energy. “It’s just about inviting people into my world,” he explains. “I want to make it as delightful and memorable as possible for the crowd, so we're definitely gonna turn up.”
Not stopping at a single night in the spotlight, Myquale plans to ride the momentum he’s garnered from his breakthrough moment, leveraging it into promo for his new project, which will be his first full-length effort since 2024’s Above All. “It might be a couple months from now, or it might be the top of next year,” he says, giving a flexible estimate of the timeline, “But I’m locked and loaded and ready to go.”
But more than just being armed with a solid rollout plan, Myquale is very intentional about achieving the goal he’s set for himself. “Right now I’m just trying to be rookie of the year,” he says, turning a basketball analogy into a declaration of purpose. But rather than aligning himself with icons like LeBron James or Steph Curry, he sees himself as more of a Kawhi Leonard type of player. “I’m very fundamentally sound but I’m trying to add more flash.”
Despite wanting to add more showmanship to his game, ultimately Myquale just wants to contribute and help the culture evolve, and his Red Bull Setlist performance is the perfect catalyst to springboard his aspirations. “When people say, ‘Where’s Hip Hop?’ Hip Hop is wherever we’re at. It’s going wherever we go,” he says, reflecting on Hip Hop’s fluid identity. “Therefore, I want to be an active participant. That’s where my ambition lies.”
Red Bull Setlist takes over Radius Chicago on October 24, with doors opening at 7 P.M.—get tickets here.