Sleepy Hallow Drops “Dirty Dan” & More
Brooklyn hitmaker Sleepy Hallow comes to life during Spooky Season, feeding his fans with regular drops and smooth melodies. Today, the East Flatbush native prepares for his next chapter, announcing Still Sleep ??, his next project. Still Sleep ?? caps an eventful year for Sleepy, who has been on a tear since emerging from prison this summer. Continuing the legacy of his GOLD-selling 2021 album Still Sleep? , which has racked up over 1.9 billion streams, the upcoming project is Sleepy’s first full-length since 2024’s Read This When You Wake Up (224+ million streams). Home to recent singles like “LOADED” and “Fine” ft. Kyle Richh, Still Sleep ?? arrives on November 13th via Winners Circle / RCA Records.
Along with the announcement of the album, Sleepy Hallow shares “Dirty Dan,” his new single and music video. Navigating the gauzy synth soundscape with lilting melody, the new song finds Sleepy in smooth operator mode, as he delivers the hook: “I’m going as hard as I can/I’m doing more than I should be/I was tryna eat, they was slappin’ my hand/Sound better, I tell ’em I could be,” sings Sleepy. In the video, Sleepy cuts loose at a cul-de-sac, showing off his cash and his foreign car as he enjoys a sunny afternoon.
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.