Incorporated in 2019, Winners Circle Entertainment includes label co-owners Sheff G and Sleepy Hallow, Eli Fross and producer Great John, who handles a majority of the label's music production. Sleepy & the rest of the Winners Circle crew are also set to release a joint project to rollout top of 2022. Sleepy has also released Still Sleep? (Deluxe), bringing in features from Chucky73, Casper Magico, Eli Fross and Skillibeng. Sleepy has been taking the project to the festival circuit landing Rolling Loud in both Miami & NY, Hot 97’s Summer Jam, Day N Vegas & more. At the moment, the song has garnered over 150 million streams and continues to hit new peaks week over week. Sleepy’s breakthrough track off the album 2055 is now RIAA Certified Platinum. Still Sleep? came out as #2 album on Apple Music, Top 20 on Billboard, 8 on Spotify’s US charts & has remained on the charts since June. Sleepy has been bringing hit records to the masses, with his major label debut album Still Sleep? that dropped June 2021. While Sheff is widely known as a founder of the Brooklyn Drill scene, it was Sleepy’s 2020 hit Deep End Freestyle (RIAA Certified Platinum) that put them on a national stage. The two connected with now business partners White and Jerm to found the independent label and release their music.
In what was initially supposed to be a fight, Sheff G and Sleepy connected/bonded over similar upbringings. Coming from East Flatbush Brooklyn, Sleepy was heavily tied into the street life that most are raised around in that area. Sleepy Hallow is one of the founding members of Winners Circle Entertainment, and breakout star of the emerging Brooklyn Drill hip-hop scene. In addition, Sleepy is planning a headline tour to be officially announced in the coming days.ĩ. Sleepy’s impressive repertoire of EPs - Sleepy Hallow Presents: Sleepy For President, The Black House, Don’t Sleep - has earned him coveted “best of” lists recognition from XXL, Complex, Uproxx and more. Recently, he was included in the BET Hip Hop Awards cypher, was announced as Billboard’s R&B/Hip-Hop Rookie of the Month (September), selected as one of HipHopDX Rising Stars 2021 and BET Amplified Artist of the Month (January). Along with the success of “Deep End Freestyle,” his emo-rap single “2055” recently became RIAA-certified Platinum. Hailing from East Flatbush, Brooklyn and one of the breakout stars of the Brooklyn Drill hip-hop scene, Sleepy Hallow came to prominence in 2020 with the RIAA-certified Platinum hit “Deep End Freestyle” which featured vocals by Fousheé.
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The program, which highlights global emerging stars, will include a forthcoming mini-documentary to premiere later this year, features in the RADAR playlist, a Spotify Singles recording, promotional support for upcoming releases, a full suite of out-of-home advertising and on-platform marketing, and social promotion. Spotify has also named Sleepy Hallow their next RADAR artist. Building on the success of his debut album Still Sleep?, the new 25-track Still Sleep? (Deluxe), produced entirely by Great John, includes new features from Chucky73, Casper Magico, Eli Fross, Skillibeng and more.
Winners Circle’s Sleepy Hallow releases Still Sleep? (Deluxe) via Winners Circle Entertainment/RCA Records.
“Look for him to continue establishing his presence as an original voice in the New York rap scene when his upcoming project lands in full.” – HotNewHipHop.“New York City has been an absolute hotbed for rising stars, and Sleepy Hallow just might be one of the biggest names on the come-up.” – Lyrical Lemonade.
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