They played that shit on the radio, and I was like, ‘Na, these niggas going crazy.’” I’m supposed to get some beats and do a song with them. “I named the song ‘Cash and Chow’ because they inspired the production,” Sleepy says of fellow drill rappers Cash Cobain and Chow Lee. Boy Meets World has much of what made the Brooklyn rapper compelling in the first place, like a smooth SWV sample on “BWV” with Fivio Foriegn, or going back and forth with fellow melodic rapper Lil Tjay on “Pain Talk.” Sleepy is also still tapped into the continued evolution of drill, despite being locked up for nearly a year. Sleepy’s lane is predicated on letting his emotions soak into his tracks and making them sink into your brain with his slippery flow. I’m still working on it, but I feel like I found my own lane.”Īfter Sheff G was arrested in 2021 for criminal possession of a weapon (he remains in jail to this day on racketeering charges), it was up to Sleepy to keep pushing Winners Circle forward and develop his own sound. I would sit in the studio and figure out my flow and perfect my craft. “Figure out your own flow,” Sleepy says when talking about how he separated himself from similar-sounding artists in the drill scene. Sleepy’s debut album, Still Sleep?, helped him burst onto the rap scene and set himself apart from artists like Sheff and Pop Smoke thanks to his syrupy delivery and unique beat selection, courtesy of Winners Circle labelmate and producer Great John. Sleepy Hallow is one of the originators of the Brooklyn drill scene, working alongside his close friend Sheff G to form Winners Circle and standing at the genesis of sample drill back in 2019. This is the first time Sleepy has been able to talk about new music since he was released from prison earlier this year after serving eight months for weapons possession, and his excitement about this next chapter of his career is palpable. He’s finished his upcoming sophomore album, Boy Meets World. The normally stoic Brooklyn drill rapper walks into the Complex studio with a grin on his face. With a bright future ahead of him as one of New York’s best rappers, Sleepy Hallow is undoubtedly a talent to watch in the future.Sleepy Hallow has been smiling a lot more lately. It has been streamed hundreds of millions of times and was a trending song on TikTok, making it the biggest hit of his young career. His 2020 single “Deep End Freestyle” is one of his best lyrical performances yet. He has frequently experimented with different styles such as trap, introspective rap, and guitar-driven beats. He also released several full-length projects of his own including Don’t Sleep, The Black House, and Sleepy For President. In 2019, Sleepy Hallow was featured seven times on Sheff G’s debut album The Unluccy Luccy Kid. 3” recognized as one of his biggest hits. 2018 saw him release a variety of both solo and collaborative singles, with “Panic Pt. With a unique style that combines hard drill rapping with an infectious singing voice, Sleepy Hallow quickly became one of his city’s most buzzed-about artists. The two released their song “Panic” in September, later releasing three follow-up tracks in the successful series. He frequently collaborates with Sheff G and is recognized as one of the top performers in the Brooklyn rap community.īorn and raised in Brooklyn, Sleepy Hallow’s debut singles came alongside local collaborator Sheff G in 2017. A pioneer of Brooklyn’s drill scene, Sleepy Hallow is a singer and rapper from New York.
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