Mysterious Hip-Hop Sensation Appleby Is About to Blow Up

Just don’t expect to see the Chicago-based singer/rapper’s face anytime soon.

Appleby’s visage is round, even cherubic. His eyes widen, and he’ll flash a fluorescent smile every time he gets excited about a topic of discussion. Which is often. But you’ll have to take my word for it—at least for now. The 23-year-old singer-rapper from Chicago, who has drawn comparisons to the Weeknd both for his velvety voice and the mystery he cultivates, refuses to publicly reveal his face. In fact, he has so far managed to keep his true identity a complete secret.

In pictures, Appleby’s face is always obscured by a hood or a hat, or tucked underneath an overcoat. But right now, at Chicago’s Classick Studios, he’s completely present—every garrulous, goofy inch of him. “Yo! How’s it going, my man?” Appleby bellows, all wide-toothed smile and chirpy, come-here-bro charm, wrapping me in a hug.

He bounds about the studio, back and forth between the recording booth and the control board, where a dreadlocked engineer puffs a marijuana pipe. As to why he won’t reveal himself to his growing fan base? “For me, it’s just plain fun,” he says. “It’s my way of allowing people to interpret the art first and formulate their own opinions about me before seeing me.”

Now going by his mother’s maiden name (his real first name is Justin), Appleby has been recording music for only 11 months. Last fall, days after he uploaded the track “Spit on Me” to his Soundcloud account, his murky, genre-bending brand of after-hours R&B received raves on The Source, Pigeons and Planes, and other influential music sites. Soon, Appleby was signed by a talent manager, and during a subsequent trip to Los Angeles, he found himself in front of hip-hop mogul Russell Simmons for an impromptu desk-side performance.

“I’m smelling roses on the go,” Appleby says of the whirlwind ascent that now has major labels itching for his signature. “To have generated this much interest without a hit song is just awesome.”

Despite such rapid-fire success, Appleby remains hidden in plain sight. Save for his mother, he says none of his friends or family are aware he’s even making music. When not at the studio, Appleby manages a Lids store in a suburban Chicago mall. “It’s a completely separate world,” he says, comparing his dull home life to the surreal professional one that recently whisked him to London and Paris for meetings with producers, fellow artists, and labels.

“I don’t talk about music at home,” he says. “Nobody around me is really interested. There’s something cool about having a secret.”

Leading a double life is nothing new for Appleby: As a child tennis prodigy, the son of separated parents spent much of the year at a posh tennis academy in Florida. Come summer, he’d retreat to the Cleveland area to spend time with his alcoholic father—that is, when his old man wasn’t disappearing.

“There were days when I would find him in the alley and I would have to bring him back home,” Appleby says of his dad, with whom he hasn’t spoken since age 17. “Or I would go to a drug house and you’d get through all the crackheads and find your father in the corner.” (Contacted by Maxim, Appleby’s father doesn’t dispute the story but reports he’s been clean for 10 years.)

After quitting tennis at 17, he returned home to Chicago and slid into a six-year depression. “Then music came along,” he says, “and it gave me a reason to wake up every day.” Appleby began recording at Classick and quickly immersed himself in the studio’s culture. “It’s like going to school every day just to see your friends,” he says of the spot that’s hosted fellow Chicago hip-hop elites Chance the Rapper, Vic Mensa, and Tink.

While finishing his album, Mask & Lies, set to drop by year’s end, Appleby is also preparing for his live debut. He practices by performing incognito at local karaoke bars, singing classic Michael Jackson songs. Appleby remains unsure how his life could change if he reveals his true identity. He can only tilt his head back and smile at the thought of being completely exposed: “I think people will probably just be like, ‘Ah, so there he is.’”

Photos by Carlos Moore