08.14.2026
Sleepy Hallow and 41’s Kyle Richh Connect for “Fine,” Their Shimmering New Single
Stream HERE
Watch HERE
Following Sleepy’s “FDO / WTW Freestyle” and His Scintillating Performance at Summer Jam, the Two Hard-Hitting Brooklyn Natives Rhyme About A Few of Their Favorite Things Over Great John’s Sped-Up
Critical Praise:
“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
The Announcement:
After emerging from prison earlier this summer, Winners Circle standout Sleepy Hallowimmediately got to work in the studio with his sights set on dominating another summer in NYC. The East Flatbush native connects with fellow Brooklynite Kyle Richh, of the popping collective 41, for “Fine,” a single perfectly-suited to heat up late summer. Produced by Great John, the Winners Circle maestro behind many of Sleepy’s biggest hits, “Fine” rides a sped-up soul sample, enhanced by John’s skittering drill percussion and sliding 808s. Responding to fan excitement about the first-ever collaboration between the two Brooklyn natives, Sleepy and Kyle Richh have electric chemistry, trading playalistic bars to attract the baddest in the room. In the video, each rapper sits on their respective thrones, dressed in designer and surrounded by NY’s finest as director Nimi Hendrix’s camera captures their confrontational charismas.
Sleepy’s release of “Fine” continues the artist’s triumphant return to the rap scene. Last month, Sleepy made a splash with “WTW? First Day Out,” a two-pack EP, with a music video featuring guest singer Annalise Azadian. “First Day Out” received a rapturous reception when Sleepy performed it at Hot 97’s Summer Jam in early August.
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“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. 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 his forthcoming album Still Sleep.
Stay tuned for more music and updates from Sleepy and Winners Circle as the summer moves along.
Shot by Peter Aboseff
Please contact Michelle or Kevin for more info.
Links:
Sheff G: Instagram | Twitter | YouTube | Spotify | Apple | SoundCloud
Sleepy Hallow: instagram | youtube | spotify | apple | soundcloud
Sleepy Hallow – “WTW? First Day Out”: https://sleepyhallow.lnk.to/firstdayout
Sleepy Hallow – “Young & Dumb”: https://sleepyhallow.lnk.to/younganddumb
Sheff G & Sleepy Hallow – “Baby I”: https://www.youtube.com/watch?v=55Z8LCaGcOY
Sheff G & Sleepy Hallow – “Lucky” ft. Bay Swag: audio | video