“A pioneer of Brooklyn drill and one of its most technically gifted lyricists” – Pitchfork
“Sheff G helped define the Brooklyn drill sound — now he’s pushing it forward” – COMPLEX
“[A] hard, forceful New York rapper with a deep, resonant voice” – Stereogum
“High area-of-impact raps…Sheff arrives at the frontlines of battle with a rare firmness and singlemindedness” – Passion of the Weiss
“Combining drill beats with softer melodies through sampling has become [Sleepy Hallow’s] forte” – Billboard
“[Sleepy Hallow] spits with the kind of ease and flash that starts block parties” – Pitchfork
With his supernatural sense of melody and butter smooth delivery, Sleepy Hallow is one of NYC’s most reliable hitmakers. Today, the Multi-Platinum Brooklyn rapper shares “Young & Dumb,” an ultra-smooth and uber-confident new single, along with a music video. Expanding outward from the drill sound that made him famous, Sleepy sinks into an immersive, Rhodes-drenched trap-style instrumental, filling the track’s cavernous space with his sticky sing-song cadence: “I see the rain, they see no sun/Pop sh*t, we young and dumb/The turtle won the race, but now the rabbit got the gun,” he lilts. In the video, directed by WhatWouldPeteDo, Sleepy relaxes with his Winners Circle brethren, playing pop-a-shot in the studio and taking his double-cup on a limo ride.
Arriving at an exciting time for Winners Circle Ent., “Young & Dumb” is Sleepy’s first new solo single of the year. Last month, Sleepy connected with his close friend and Winners Circle running mate Sheff G for “Baby I,” a danceable anthem produced by frequent collaborator Great John. Along with Sheff’s recent single “Him,” “Young & Dumb” paves the way for We Won, Sheff & Sleepy’s collaborative album, coming soon via Winners Circle / RCA Records.
“Young & Dumb” lands as Sleepy Hallow and Sheff G continue their journey in accountability, maintaining strong positive and creative spirits through their prison sentences. These singles, and what’s to come, seek to remind the rap game of all they have already accomplished, promising their family and fans that they can rely on them no matter the circumstance.
Sleepy Hallow is one of the founding members 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 “Hallow Heart,” 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.
With their joint album We Won coming out soon, Sheff G and Sleepy Hallow are ready to make an impact that their city will feel for a long time.
Stay tuned for more music and updates from Sleepy and Sheff.
Courtesy of RCA Records
Please contact Michelle or Kevin for more info.
Sheff G: Instagram | Twitter | YouTube | Spotify | Apple | SoundCloud
Sleepy Hallow: instagram | youtube | spotify | apple | soundcloud
Sleepy Hallow – “Young & Dumb”: https://sleepyhallow.lnk.to/younganddumb
Sheff G – “Him”: https://sheffg.lnk.to/him
Sheff G & Sleepy Hallow – “Baby I”: https://www.youtube.com/watch?v=55Z8LCaGcOY
Sheff G & Sleepy Hallow – “Lucky” ft. Bay Swag: audio | video
Sheff G – Proud of Myself: https://sheffg.lnk.to/proudofmyself
Sheff G – “Never Again” ft. Lil Tecca: https://sheffg.lnk.to/neveragain