Oluwawemimo Hassan, who raps as WemmyMo, dropped his first song while he was still in high school—and it got nearly two million plays. Credit: Nolis Anderson for Chicago Reader

In the summers, the gym at Uplift Community High School in Uptown often serves as a training facility for basketball talents who came up in the neighborhood and have returned for the off-season. But between those sessions, it provides the favorite athletic pastime of the Chicago teenager: open gym. In summer 2015, 16-year-old aspiring rapper Oluwawemimo “Wemmy” Hassan, aka WemmyMo, had just finished three hours of hoops at Uplift and was hanging with a few friends outside the gym, where the lake breeze felt perfect through their sweat-drenched T-shirts. He couldn’t know it, but in a few moments his life would change forever.

As Hassan and his friends teased one another about their game and discussed their plans for the rest of the day, a boy he guesses was around their age pulled up on a bicycle and fired what sounded like an entire magazine of bullets at them. As if by divine intervention, no one was killed or even hurt.

“I was never into the streets like that, and people knew that,” Hassan says. But some people he often hung out with had gotten entangled in a gang conflict that provoked the shooting, and their enemies involved Hassan by mistake. “It was a case of being with the wrong people in the wrong place at the wrong time,” he explains. “It was that life-endangering experience that really made me sit back and reevaluate the company I keep. Since then, my entire circle has been my blood cousins. I trust them to never put us in situations like that.”

These days Hassan, now 20, is no longer an aspiring rapper—he’s a must-see, with an EP, a compilation, and a full-length mixtape under his belt (and another on the way). And he’s grown his career with help from his family. “Since I’ve brought them more closely into what I’m doing, they’ve started to get into music themselves,” he says. “My DJ for my performances is my cousin Joshua. My cousins Ali and Ced have started to work toward becoming artists themselves.” You can see them dancing in many of Hassan’s videos, or even onstage as hype men at his shows. They help him out in the studio as on-the-spot critics and A&R people.

The WemmyMo experience is family oriented because Hassan internalized that value early—something he says is typical of the Nigerian American community. His relatives are his biggest boosters, and being able to provide for his mother is one of his main drivers. “My mother has been a major supporter of my music since she first heard it,” he says. “I was hiding it at first, but one of my cousins was blasting my music after church and she heard it. Now she’s putting her friends and coworkers onto it.”

Hassan is ready to go all-in on music as a career, but his mother is still reluctant to accept such an unpredictable pursuit as his primary source of income. “The stereotypical route is always school, then degree, then a good job,” Hassan says. “It’s cool to be able to show my mom who wrote about me or who posted my music, but that means little when we still struggling to figure out what we eating tonight.”

Because Hassan has grown up in poverty and exposed to violence—and because he still has to consider his family’s peace of mind when he makes decisions—his view of success has evolved to take those factors into account. In his view, they aren’t bugs to be worked out or roadblocks to be avoided; they’re an essential part of his journey. “Growing up in an immigrant family, there’s pressure to follow the average blueprint to success, because people feel like you’ll end up suffering just like them,” he says. With his second full-length project, Suffering and Smiling 002, due next month, he aims to explore that pressure—and his resistance to it—in music. “The way I see it, you have a choice to suffer a bit now in order to celebrate and smile later, or you do it the safe way now and spend the rest of your life suffering.”

Hassan hopes to use his music to help provide for his family.
Hassan hopes to use his music to help provide for his family.Credit: Nolis Anderson for Chicago Reader

Hassan used the songs and visuals for his 2018 debut mixtape, Bittersweet, to help establish the public image of WemmyMo: an energetic young artist with an affinity for popping colors and childhood nostalgia, who delivers his impressively polished lyrics in a relaxed style. And he foreshadowed the themes and presentation of Bittersweet with the first song he ever released, “Misunderstood,” which came out in May 2016—a little more than a week after he recorded it at Chicago’s Big Wet Studios. Its lyrics are a walk through Hassan’s struggles at the time, told as a cautionary tale.

“When I wrote ‘Misunderstood,’ I was coming off a bad breakup, I was involved in some street shit that I truly had nothing to do with, I didn’t make the basketball team ’cause I missed the tryout. I was going through a lot,” Hassan says. “The common denominator for all those things was that I felt misunderstood. By the basketball coach, by the guys from my neighborhood, by the girl I had been dating. So I rapped how I felt.” He followed the single with the January 2017 EP Styles for the Free.

On “Misunderstood” and Styles for the Free, Hassan takes an introspective look at what he was going through at the time, while Bittersweet is more retrospective—it’s about nostalgic reflection on the simple daily trials he faced as a teenager. “I look at the projects I create as almost like a timeline,” he says. “Bittersweet is me as a high school kid, having fun, not ready to grow up. The cover is even a picture of me when I was a shorty.” For a debut mixtape, Bittersweet is surprisingly refined. Its skits, its song-to-song cohesion, and its accompanying visuals all feel on par with mainstream LPs by artists with several full-length studio releases out.

“It’s funny, because the songs on Bittersweet are mostly just rough drafts,” Hassan says. “I never went back to songs like ‘Holy Vibes’—I just did the song and that was it. That’s something I’ve changed since starting this new project.”

One of Bittersweet‘s standout qualities is its production. Hassan isn’t the sole or main producer on his tracks, but he likes to be involved in the process. For the EP he chose instrumentals that sample soul music, which helps the songs do more than just talk about the “good old days”—they take you there. “I was at church every Sunday growing up, so interpolating that kind of music came naturally,” he says. “I’d be lying if I said I listen to that kind of music daily, but I am very much a student of hip-hop. I understand what samples like that can add to a song.”

Hassan first learned to play music as a kid in church. “When I was young, I was doing everything musical in church,” he says. “I was playing drums and piano, and I was in the choir. Music has been a part of my life since I could remember.”

Not till high school, though, did music become Hassan’s focus. “Sports was always my main interest growing up. I played football and basketball,” he says. “Early on in high school, I got injured playing football, and the news about football players dying from CTE made my mother put an end to it.” After he missed basketball tryouts in 2016, during his sophomore year of high school, he was left with no obligations but school to fill his time.

“I knew what the traditional route was: high school, college, then job. And I knew that I wasn’t comfortable just being regular,” Hassan says. “I told myself I was gonna save all this money up and buy equipment and download Ableton or something. Whole time, I was still writing raps and sharing them with my cousins.”

Later in 2016, Hassan attended an after-school open mike at Harold Washington Library, where he gave his debut performance as a rapper. “I was a little nervous, ’cause it’s my first time performing my raps in public,” he says. “But I felt comfortable onstage. I’d been singing in front of my church since I was little.”

The performance went well enough that Hassan hurried into the studio that same week. “The open mike was on Monday. By Friday I released a freestyle video on YouTube,” he says. “In about two more weeks, I released ‘Misunderstood.'”

Hassan had found the instrumental for “Misunderstood,” by Brooklyn producer Ty Goods, online. He bought it but didn’t stay in touch with Goods—the producer didn’t know Hassan had made a song from it till he stumbled across the finished product a year later. Goods’s beat samples the 1984 Sade cut “Sally,” setting the tone for Hassan’s rap career, which continues to rely on storytelling and reminiscence.

To complete the package, Hassan adds a splash of color with his fashion sense—he might combine thrifted Chicago Bulls championship gear with a favorite vintage Gucci sweatshirt—and with his vivid, playful Hype Williams-esque visuals, such as the video for the Lauryn Hill-sampling Styles for the Free track “Watch Out.” That fun, distinctive persona was in place from the beginning, and Hassan felt ready to blow up right out of the gate. “Misunderstood” reached a lot of ears, but for whatever reason, after that his numbers didn’t climb the way he’d hoped.

“My first song hit damn near two million plays. Some people don’t even see that until five, ten years in, or never,” Hassan says. Frustratingly, he hasn’t equaled that success since. “I know that I’m great at this, and it just didn’t feel like things were going up at the rate they should’ve been.” In 2018, after graduating high school, he caved to his mother’s desire to see him finish his education. He enrolled at Harold Washington College, where he studied business and marketing.

“It took me away from the music a bit, but my freshman year of school went great. I had a 4.0 GPA, but I still wasn’t satisfied with where life was going,” he says. “I felt like I had achieved what you’re supposed to achieve when you put your all into school, and I still wasn’t satisfied. It was depressing. That just means that that isn’t what I’m meant to be doing.”

Hassan spent summer 2019 soul searching. Conflicted about how to move forward, he would walk to the lake at Montrose Harbor and think, watching the skyline illuminate the water. “I started coming here to give myself space to let off steam, to just sit with my thoughts,” he says. “The view is beautiful, the sound of the waves is relaxing—it’s like a safe space. Honestly, coming out here has made me realize how much I love nature. It’s beautiful.”

He was leaning toward leaving Harold Washington to focus solely on music. In fact, he was already nearly done with the compilation 10:15, which dropped in October and collects tracks that won’t make the cut for Suffering and Smiling—”some new, some old, some I just fucked around on, and some I didn’t even bother getting the proper mix for.” He says it’s a way to clear the decks for the more focused and tightly curated sound he’s going for on the forthcoming full-length.

WemmyMo's latest full-length, <i>Suffering and Smiling 002</i>, is due out next month.
WemmyMo’s latest full-length, Suffering and Smiling 002, is due out next month.Credit: Nolis Anderson for Chicago Reader

When it came time for Hassan to register for the 2019 fall semester, though, his mother began to ask questions. “She wanted me to keep going to school, but I know that isn’t me. So I compromised,” he says. It helped that he qualified for more financial aid than he needed to cover his university bill. “I registered for an online class to keep her happy, and to give myself the space I need to create—and to collect that financial-aid refund check.”

The money went toward buying beats and booking engineers, both of which he needed to take advantage of free studio time he had at the River North campus of the SAE Institute—courtesy his friend and engineer Trevor James, who’s a student there. Hassan used that studio time to capture his experiences as they unfold—that is, the “suffering” part of Suffering and Smiling. “It’s kind of weird talking about it now, because a lot of those things are still going on,” he says. “I just got through talking to my mom about the school stuff today.” Suffering and Smiling 002 (there is no Suffering and Smiling 001) is scheduled to drop in February 2020, because Hassan wants it to capture the essence of winter.

“There’s just a generally more dark mood around the winter,” he says. “Like seasonal depression for everybody. I know that this project is much darker than things I’ve released in the past, but the thing I find most important is that it’s still me.”

Hassan says Suffering and Smiling 002 touches on growing up in poverty, balancing school and his dreams, dealing with depression, and enduring betrayal from industry acquaintances. But the subject matter isn’t the only way Suffering and Smiling differs from his previous releases. “Now I’m almost back in my producing bag,” he says. “I’m much more involved in the beat-making process—I’m writing songs so that they come together as the beat does. It’s a more ground-up approach than before.” While in the SAE studio working on this mixtape, Hassan and James, who works as SirTrevorJames, had a long talk about whether to use a soft clipper or a limiter to control the amplitude of an ad-lib track, and spent ten minutes dragging and dropping a five-second clip in different spots in order to ensure a line hit exactly when they wanted it to.

Hassan has an equally meticulous plan for the rollout of this project. “The album could technically come out tomorrow and be complete. It just wouldn’t be to my satisfaction. There are visuals and singles for it that I want to release early. They’re setting the tone.”

DJ Balor, aka Hussein Atoro, is one of Hassan’s cousins as well as one of his most consistent collaborators on Suffering and Smiling. He says Hasssan’s career inspired him to start producing in 2017. “I always wanted to do music, but I never had the money for it,” Atoro says. “When I saw Wemmy get into it, it opened the door.”

Hassan continues to look to his family for guidance, this time to help him find the right balance between his original sound and the subtle new experimentation in his music. He’s started adding brooding instrumentals to complement the weight of his writing, for instance, as well as building beats around his lyrics rather than vice versa.

“If I’m not in the studio by myself, then I’m with my cousins,” Hassan says. “They give me the criticism and feedback I need. Like the other day, one of them told me I needed to slow down the BPM of a track. Like the song was moving too fast for my voice. They catch things that I can’t.”

Hassan believes that the challenges he faces now are preparing him for the success he desires—and not just for his own sake. His family needs whatever support he can give, and that remains a big part of what motivates him. “I’ve become a mature artist and a more mature person overall,” he says. “When I started, I felt like I had to prove something. I had to show that I belong here. Now, it’s about being able to provide for my family and live the life I want for myself.”  v

Nolis Anderson for Chicago Reader