Makonnen Sheran, a.k.a. iLoveMakonnen. Illustration by Andy Friedman

In late April of this year, Makonnen Sheran, the hip-hop artist known as iLoveMakonnen, was lying on his back after a pre-show sound check at Bowery Ballroom. He spoke with me while he looked at Snapchat on his phone, which he held above his head with both hands as if it were a prized baby. I asked him what he was going to wear onstage later that night. “Just regular, dumb-person clothes,” he said. “Maybe white pants—something I can throw up on, and people would see the throw up. They’ll be like, Oh, my god, he was so nervous he threw up all over that white outfit. What a dweeb!”

Sheran has a penchant for conjuring up darkly funny images. Last August, his quirks were thrown into the limelight when his song “Tuesday” was remixed by Drake and garnered more than a hundred and ten million views on YouTube. The opening shot in the music video for “Tuesday” is, at first, quite normal: a sea of hands undulating in a club. Then things get strange. An object that looks like a human head is flung into the air above the revellers. When a strobe light flashes, it becomes clear that it is, in fact, only a mannequin’s head—one that is sporting a Ziggy Stardust-esque makeup job and a neon Glasgow smile.

Sheran’s peculiarities have deep roots—a stroke of authenticity in a pop-music scene in which attention-grabbing aesthetics often feel like they’re made up on the spot. The mannequin in the video has been a part of Sheran’s life for years, and, like a longstanding friend, he has given her a name, Martha. Alongside her vivid cosmetics, Martha has a partially shaved head and “ILOVEMAKONNEN” written in black marker just under her red hairline. Sheran inherited his interest in styling from his mother, who worked and taught classes as a cosmetologist for years. He lived with her in Atlanta during his adolescence; his parents divorced soon after he was born, and throughout his early childhood he stayed with his father in Los Angeles. In Atlanta, his mom bought him a keyboard and sung vocals over the tracks he made with it, becoming Sheran’s first musical collaborator.

In 2008, a few days after his high-school graduation, Sheran was involved in the accidental death of one of his friends, and was put under house arrest for two years as the case puttered through the Georgia court system. While he was stuck in his mother’s home with an ankle monitor, he connected with the outside world by using the Internet. He spent much of his time interviewing musicians he met online for a blog he started, called The Newness, which featured artists whose work was floating around cavernous social sites like MySpace and who hoped to find people to listen their creations.

After his release from house arrest, Sheran was sentenced to five years of probation, and in this period he began to make more of his own music, and lots of it. From 2011 to early 2014, he self-released almost a dozen mixtapes, jumping between genres and sounds with Martha by his side. On “Sneaky Lady,” released in 2012, he channels Elton John, breathily thumping vocals over a rushing piano, while on “The Newness,” a song from 2011, he raps with a throwback naïveté over a swishing, reverbed beat about “Bugatti dreams becoming reality.” In the latter song’s video, Sheran plays with Martha’s inanimate head for the camera like a frolicking incarnation of Caravaggio's “David with the Head of Goliath,” with a T-shirt instead of a tunic.

Sheran’s prolific output and knack for making oddly catchy music soon got him noticed in the Atlanta music scene. Established hip-hop producers in the area, such as Mike Will, DJ Spinz, Sonny Digital, and Metro Boomin, began working with him in 2014, recording new tracks for Sheran’s mixtape “Drink More Water 4,” as well as rerecording songs that Sheran had produced and released by himself, like “I Don’t Sell Molly No More” and “Sex, Love, Ecstasy.” The raw and eclectic sounds of his earlier recordings took on a more polished quality, pushing Sheran further into mainstream acceptance. A few months later, the Drake remix of “Tuesday” was being played all over the world.

Despite his success, the troubling experience of being isolated in house arrest as a young man has left a discernible mark on Sheran, and he spoke with me about feeling lonely and depressed. But he finds solace in entertaining others: he said that his goal in his shows is to “have people smiling and happy.”

At Bowery Ballroom, Sheran kept kidding around. I asked him about his planned releases on OVO Sound, Drake’s Toronto-based record label, to which he was signed at the beginning of last September. He said that his new music would feature only the pan flute, because he wanted to start playing live shows at Medieval Times, the national chain of dinner-theatre venues where audiences watch jousting and various other “medieval” performances while eating a meal. In fact, Sheran said that he hadn’t visited a Medieval Times since he went to a branch in California as a child, but he wanted to go again soon.

A few months later, we were at a Medieval Times show in Lyndhurst, New Jersey. Sheran had his eyes fixed on a horseman who was wearing a red-and-black tunic over a chain-mail suit. “I want to dress like that,” he said. Instead, he was wearing shiny black jeans, an Adidas bomber jacket, and a recently acquired paper Medieval Times crown that rested on his dyed-blond curls. The knight-actor and his steed trotted across the sandy floor as an announcer encouraged the crowd to “feel the common pulse of man and horse.” Sheran giggled.

His new EP, “I Love Makonnen 2,” which was released on November 20th, is (probably for the best) entirely devoid of the kind of music you’ll hear at Medieval Times. “They wouldn’t let me put it on there,” Sheran insisted. Rather, it’s a mixture of songs that he says are “for others”—pop-leaning trap and hip-hop that will feel comfortable in a club—as well as slower, brooding tracks that are “more for me.” On the latter, he reveals a unique singing voice that evokes a cigarette-smoking burlesque singer at the end of a shift—a willfully teetering vibrato that slides into honeyed falsetto at a moment’s notice. As a result, the EP is both significantly different from and reassuringly similar to his early musical forays. On songs like “Trust Me Danny,” we get a freshly manicured version of Sheran, one that seems built for mass consumption. “Being Alone with You” reverts to his D.I.Y. bedroom-rap sound, but now Sheran has the confidence as well as the tools to fully explore and exploit the idiosyncrasies of his voice.

A waiter poured a jet of steaming Dragon’s Blood (tomato soup) from a carafe into pewter bowls with handles—Medieval Times prides itself on the (debatable) historical accuracy that comes with not providing cutlery. Sheran pulled out his phone, took a picture, and posted it to Snapchat. “I love it!” he said. “I wish I could have more.”