“Through tracks like ‘Panic Part 2’ and ‘Panic Part 3,”’a feeling emerged in the borough that Sleepy had a gift for storytelling” – Pitchfork
“Sleepy delivers hard-hitting bars with aggression and intention as he talks about everything from his street lifestyle to his come-up” – Complex
“I’m more partial to Sleepy Hollow, whose voice is fuller and more burly than it is raspy” – The Ringer
“Sleepy Hollow’s erratic, clever rhyme style and Sheff G’s cold-as-ice cadence make them a unique proposition” – NME
New Artist to Watch in 2020 – HotNewHipHop
Blending pop-savvy melody with vivid accounts of life in the street, Brooklyn rapper/singer Sleepy Hallow crafted several songs that have taken New York City by storm. Following songs and videos with streams in the millions, the right-hand man to Sheff G became a major player in the NYC scene with his October 2019 debut mixtape Don’t Sleep. With over 100 million streams across platforms in the books, the rapper whose name plays on the headless horseman in gothic literature comes from his own haunting world on the block. Look out for Sleepy For President, a new album from the East Flatbush native in June 2020 via Winners Circle Ent./EMPIRE.
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.
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