Is Sleepy Hallow ‘Still Sleep ??’
With his smooth melodic style and unimpeachable status in the streets, Sleepy Hallow is ready to reclaim his throne. The Brooklyn native issues a wake-up call with Still Sleep ??, his new album, out now via Winners Circle / RCA Records. Spanning 23 tracks, the new album is an ambitious effort, each song defined by Sleepy’s liquid hooks, flirtatious banter, and slick stick talk. Following up Sleepy’s successful 2022 Still Sleep? project (1.9 billion streams, home to 4x Platinum single “2055), the sequel is equally impressive, stacked with A-list guests and potential radio hits.
Along with the album, Sleepy shares the video for highlight track “Sad Face,” a collaboration with Nigerian superstar Davido. The new song, produced by Sleepy’s frequent collaborator Great John, combines the sounds of Sleepy’s Brooklyn drill and Davido’s Afrobeats, creating a breezy banger that will fill up dance floors on both sides of the Atlantic.
Still Sleep ?? is home to Sleepy’s red hot recent singles, which he has released in a steady stream since emerging from prison this summer. The tape plays host to “WTW? Freestyle” and “First Day Out,” his initial messages following his prison sentence, which set the block aflame earlier this year. Additional singles that find a home on the project include the smoldering “Young & Dumb,” the Great John-produced “LOADED,” the swelling “Dirty Dan,” and the party-starting “Fine” ft. Kyle Richh of 41. Sleepy populates the tracklist with plenty of new highlights, including collaborations with Loe Shimmy, DDG, and Ffawty.
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.
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. Over the summer, Sleepy made a splash with “WTW? First Day Out,” released “Young & Dumb,” a confident and melodic single, rocked the stage at Summer Jam, and he made an appearance on his close friend Sheff G’s Weight On Me: The Album, out now via Winners Circle / RCA Records.