Sleepy Hallow Returns With “FDO” and “WTW Freestyle”
Sleepy Hallow used his recent time in prison to reflect on his responsibilities as a community leader and his mission as an artist, emerging with a new sense of purpose this past May. Today, the Multi-Platinum Brooklyn native makes his triumphant return to the rap scene, releasing “WTW? First Day Out,” a two-pack EP via Winners Circle / RCA Records.
Each produced by frequent collaborator Great John, “WTW? Freestyle” and “First Day Out” encapsulate the rapper’s state of mind as he regains his freedom. Rhyming with lilting melody over Great John’s insistent percussion and descending synths, Sleepy speaks on loyalty and leadership on “WTW? Freestyle,” expressing his desire to find comfort and love and praying for the serenity to accept the things he can’t change. On the other hand, “First Day Out” is a celebratory anthem, with a hook from singer Annalise Azadian, as Sleepy describes his feelings of invulnerability and immense accomplishment amidst the new chapter in his career.
The EP arrives with a music video, directed by Nimi Hendrix, featuring both songs presented back-to-back. Starting with clips of Sleepy making the most of this prison sentence, the video shows off the rapper’s platinum plaques before he heads to Downtown Manhattan to meet the public upon his release from prison. The video for “WTW? First Day Out” drops at 3pm on Sleepy Hallow’s YouTube channel.
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. 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.