Sleepy Hallow is one of the founding members of Winners Circle Entertainment, and breakout star of the emerging Brooklyn Drill hip-hop scene. Coming from East Flatbush Brooklyn, Sleepy was overcoming the struggles of the environment in Brooklyn that most are raised around in that area. In what was initially supposed to be a fight, Sheff G and Sleepy connected/bonded over similar upbringings. The two connected with now business partners White and Jerm to found the independent label and release their music. 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. Sleepy has been bringing hit records to the masses, with his major label debut album Still Sleep? that dropped June 2021. Still Sleep? came out as the #2 album on Apple Music, Top 20 on Billboard, 8 on Spotify’s US charts & has remained on the charts since June. Sleepy’s breakthrough track off the album 2055 is now RIAA Certified Double Platinum. Now, the song has garnered over 330 million streams and continues to hit new peaks week over week. 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. Sleepy has also released Still Sleep? (Deluxe), bringing in features from Coi Leray, Chucky73 and Eli Fross. Last year, Spotify also named Sleepy Hallow their next RADAR artist and was included in the BET Hip Hop Awards cypher. Additionally, he was announced as Billboard’s R&B/Hip-Hop Rookie of the Month (September), selected as one of HipHopDX Rising Stars 2021 and most recently was BET Amplified Artist of the Month. Sleepy and the rest of Winners Circle are also set to release new music very soon.