Sleepy Hallow “Loaded”
Sleepy Hallow emerged from prison and immediately got to work, releasing anthem after anthem to animate the streets in Brooklyn and beyond. Today, the Brooklyn drill pioneer keeps his hot streak going, teaming up with producer Great John to release “LOADED,” his new single and music video. Staying laid back atop Great John’s chirruping vocal samples and stuttering synths, Sleepy settles into a melodic groove, detailing his rise from the bottom to his current “frozen” status with aplomb. In the video, Sleepy takes a quick trip to Miami, where he romances a boatful of baddies on a yacht through the city’s canals, before retiring to a luxury apartment for the night.
“LOADED” is the latest missive from Sleepy Hallow, continuing a red hot 2026 for the East Flatbush native. “LOADED” follows “Fine,” a long-awaited collaboration with 41 heavy-hitter Kyle Richh. Earlier in the summer, Sleepy made a splash with “WTW? First Day Out,” a two-pack EP, with a music video featuring guest singer Annalise Azadian. Sleepy made his return official when he rocked the stage at Hot 97’s Summer Jam in early August. Sleepy is currently hard at work on Still Sleep? 2, his next album and the sequel to his breakout 2021 project. Home to his recent singles and plenty of additional new highlights, Still Sleep 2? is scheduled to arrive just in time for Halloween via Winners Circle / RCA Records.
Sleepy Hallow is a founding member of Winners Circle Entertainment, and one of the key breakout stars of the Brooklyn Drill hip-hop scene. Coming from East Flatbush Brooklyn, Sleepy worked hard to. overcome the struggles of the environment in Brooklyn that most are raised around in that area. Though peers expected the two big personalities to clash, Sheff G and Sleepy connected/bonded over similar upbringings. The two connected with now business partners White and Jerm to found the independent label Winners Circle to release their music.
Sleepy Hallow kept busy before his current time away, and continues his flurry of activity even from behind bars. 2025 was highlighted by the resurgence of his hit single “Anxiety” ft. Doechii and “The Hallow Heist,” an immersive virtual concert experience, created in Fortnite and produced in partnership with Winners Circle, RCA, and Sony Music. Boosted by a TikTok trend that swept the platform, “Anxiety” became one of 2025’s biggest hits, with hundreds of millions of streams across platforms and a #45 peak on the Billboard Hot 100.
Riding high off the momentum of 2024’s Read This When You Wake Up project (224+ million streams), Sleepy Hallow has scored several RIAA-certified hits throughout his career, most notably the quadruple-Platinum “2055” (over 1 billion Spotify streams) and the Platinum “Deep End Freestyle” featuring Fousheé. Additionally, Sleepy’s 2021 album Still Sleep? earned Gold-certification, along with single “Breaking Bad” ft. Sheff G, while “Molly” ft. Sheff G is now Platinum-certified. Most recently, Sleepy released “Young & Dumb,” a confident and melodic single, in May 2026, and he will make an appearance on his close friend Sheff G’s Weight On Me: The Album, out on July 24th via Winners Circle / RCA Records. Sleepy plans to drop much more music this year, including a joint project with Sheff and the forthcoming Still Sleep 2?.