Sleepy Hallow does not hesitate to illustrate the ugliest sides of life in its music. He knows his fans feel empowered seeing others go through the same struggles as them, and he’s motivated by their responses to his songs.
“In my comments, people tell me how much I’ve helped them through shit, and I’m always really surprised because I deal with my own shit too,” says the Brooklyn rapper by-way-of- Jamaica. “But there will be some things I will say where people will say that was motivation for them. It’s always motivation for me to open up more and let them know that I’m going through shit too. All the everyone has something to do.
Sleepy first appeared on the New York rap scene while working with close friend and Winner’s Circle bandmate Sheff G. The two Brooklyn rappers supported the drill move, but chiseled their own way with a new approach to sound. Sleepy turned heads with his popular mixtape Do not sleep in 2019, before releasing his first studio album Are you still sleeping? in 2021, and established himself as one of the first New York drill artists to go viral using samples in his songs.
The sampling exercise has become a popular sound in boroughs like the Bronx, but Sleepy Hallow songs like “Deep End Freestyle,” “2055” and “Basketball Dreams” were making waves on TikTok before most artists current sampling exercises find mainstream appeal. Sleepy is quick to point out that he puts his own spin on the sound: while most artists sample classic R&B songs to tap into a sense of nostalgia, he prefers obscure tracks he finds at random. And it harmonises with the sample in a uniquely syrupy way, floating over the melodic beats of must-have producer Great John.
His latest single “Die Young” borrows from the track “Memories!” by alternative artist 347aidan. whom Sleepy encountered while casually scrolling through social media. Then they connected through their management and “Die Young” was born. “I don’t wanna die young, so I stay with a stick,” Sleepy raps, dumbfounding the hook of “Memories!” which caught his eye in the first place. The song will arrive on his next project, which Sleepy says will incorporate vibes that will appeal to the different demographics of his fan base.
However, it wasn’t all easy during Sleepy’s rise to prominence. Shortly after the release of Are you still sleeping?, Sheff G was sent to prison for two years after pleading guilty to criminal possession of a firearm. This left Sleepy without his right arm, but he says he had learned to be self-reliant as an artist in previous years. “We were always going [to the studio] together, then [Sheff] was growing as an artist and I was growing as an artist,” Sleepy says, explaining what it was like growing up under Winner’s Circle. “Basically, we learned to be able to fend for ourselves as individual artists.”
Currently, Sleepy is dealing with his own legal issues. Although details remain unclear, his Instagram page has hinted that he is currently in prison by posting messages such as “release me” in recent days. When contacted for comment, his label provided the following statement to Complex: “Sleepy Hallow is currently incarcerated. Sleepy and the team at Winners Circle Entertainment appreciate the support they have received from collaborators and fans during this time. period.
Back in mid-June, we spoke with Sleepy about originating the drill wave sample, a status update on Sheff G, and what fans can expect from his upcoming album. .
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