Sleepy Hallow

Although just 20 years old, Sleepy Hallow has experienced plenty. Born in Jamaica, Sleepy’s family immigrated to Brooklyn when he was in early grade-school, around adolescence, he started spending his time in the neighboring Flatbush section. “There’s mad different people out here, and most of ‘em are West Indian. It’s just a hustle for most of us, especially young people.” As a first-generation immigrant, Sleepy says that while he was a class clown, he mostly kept to himself after the bell. Peers had a different life than the kid with low-hanging eyes (earning him the “Sleepy” nickname) and nearly 10 relatives crammed into a two-bedroom apartment. Early on, Sheff—who he’d met in Flatbush—was the exception.“We were alike, wanted the same things, and had the same problems in our families. Before Sheff, everybody was just an associate to me; I never had real friends like that. He’s my brother.”

It was around meeting Sheff that Sleepy began writing verses that reworked songs from the radio. He recalls, “I used to tell my mother from the age of 12, ‘I know I’m gonna be a rapper.’ I had no other goal.” Meanwhile, he studied the greats, from Kendrick, Drake, and Cole to Biggie and Big L. Although he did not enter a recording studio until his upper-teens, Sleepy knew what he wanted to say. At a time when sections of The Big Apple were making local street anthems, Sheff and Sleepy waved a proud flag for Flatbush. “Everybody in a hood has their songs. These songs tell you where they’re from, what they’re repping. It was our turn.” Sheff made “No Suburban,” a song with more than 7 million views. “We had to show people how we do, how we get lit.” Videos and remixes emphasized the life; more songs followed. Sleepy featured on “Panic 3,” “Automatic,” and 2019’s “Flows.” Each reality-rooted visual achieved millions of views.

However, in the lead-up to Don’t Sleep, Sleepy discovered a new vibe. “I Get Luv” opened doors. “That’s my new style of my rapping.” With a warm chord, hard drums, and a catchy chorus, it’s street-pop. “I’m liked, but at the same time, I’m hated—and I don’t really care. I’ve got my team with me, and I’m good,” he says of the song’s message. Albeit a new sonic direction, it shows confidence and distinction. Meanwhile, video single “Bestie” deals with a guy also maneuvering for his girl’s best friend. “It’s all a feeling and a mood. I make songs off of that.”

However, even beneath the sweet sounds is Sleepy’s grim reality. Don’t Sleep’s artwork depicts Robert “Yummy” Sandifer. The 11-year-old Chicagoan who was on the cover of TIME, after he was killed by fellow gang members in 1994. “When I read his story, I felt like I could have been him,” Sleepy solemnly says. The jarring image represents real-life horror stories, taking place on our streets. As a survivor with ways to go, Sleepy Hallow’s music hopes to be an awakening.