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Sleepy Hallow Releases “Still Sleep? (Deluxe)” With New Features From Chucky73, Casper Magico, Eli Fross, Skillibeng & Others

[Cover Artwork Credits: Ryan Dylan Selkirk (Aylo), Kirby “Kurve” Esquea, Nick Baran and Sleepy Hallow]



“Sleepy Hallow’s voice is just as menacing as his name suggests.” – Billboard

“New York City has been an absolute hotbed for rising stars, and Sleepy Hallow just might be one of the biggest names on the come-up.” – Lyrical Lemonade

“Look for him to continue establishing his presence as an original voice in the New York rap scene when his upcoming project lands in full.” – HotNewHipHop

[New York, NY – October 8, 2021] Today, Winners Circle’s Sleepy Hallow releases Still Sleep? (Deluxe) via Winners Circle Entertainment/RCA Records. Building on the success of his debut album Still Sleep?, the new 25-track Still Sleep? (Deluxe), produced entirely by Great John, includes new features from Chucky73, Casper Magico, Eli Fross, Skillibeng and more. (complete tracklist below.)

Listen to Still Sleep? (Deluxe) here:

Spotify has also named Sleepy Hallow their next RADAR artist. The program, which highlights global emerging stars, will include a forthcoming mini-documentary to premiere later this year, features in the RADAR playlist, a Spotify Singles recording, promotional support for upcoming releases, a full suite of out-of-home advertising and on-platform marketing, and social promotion. RADAR-branded Sleepy Hallow photos can be found HERE.

Hailing from East Flatbush, Brooklyn and one of the breakout stars of the Brooklyn Drill hip-hop scene, Sleepy Hallow came to prominence in 2020 with the RIAA-certified Platinum hit “Deep End Freestyle” which featured vocals by Fousheé. Along with the success of “Deep End Freestyle,” his emo-rap single “2055” recently became RIAA-certified Platinum. Recently, he was included in the BET Hip Hop Awards cypher, was announced as Billboard’s R&B/Hip-Hop Rookie of the Month (September), selected as one of HipHopDX Rising Stars 2021 and BET Amplified Artist of the Month (January). Sleepy’s impressive repertoire of EPs – Sleepy Hallow Presents: Sleepy For President, The Black House, Don’t Sleep – has earned him coveted “best of” lists recognition from XXL, Complex, Uproxx and more. In addition, Sleepy is planning a headline tour to be officially announced in the coming days.

Still Sleep? (Deluxe)  Tracklist:
*Indicates new tracks

  1. Make You (Extended)
  2. Winners Freestyle
  3. Luv Em All
  4. Don’t Front Freestyle
  5. Gloomy Conscious
  6. Hit Man
  7. Down Hearted
  8. 2055 (ft. Coi Leray)
  9. Basketball Dreams Remix (ft. Eli Fross)
  10. 2 Sauce Remix (ft. Skillibeng)
  11. Mi No Sabe Remix (ft. Chucky73 & Casper Magico)
  12. Basketball Dreams (Intro)
  13. 2 Sauce
  14. 4or Daze
  15. 2055
  16. Make You (Snake Proof)
  17. Equal
  18. Scrub
  19. Sleepy Freestyle
  20. Chicken
  21. Mi No Sabe
  22. 1999
  23. Murda She Wrote (Outro)
  24. Low Key (Bonus)
  25. Tip Toe (ft. Sheff G)

Sleepy Hallow is one of the founding members of Winners Circle Entertainment, and breakout star of the emerging Brooklyn Drill hip-hop scene. Coming from East Flatbush Brooklyn, Sleepy was heavily tied into the street life that most are raised around in that area. In what was initially supposed to be a fight, Sheff G and Sleepy connected/bonded over similar upbringings. The two connected with now business partners White and Jerm to found the independent label and release their music. While Sheff is widely known as a founder of the Brooklyn Drill scene, it was Sleepy’s 2020 hit Deep End Freestyle (RIAA Certified Platinum) that put them on a national stage. Sleepy has been bringing hit records to the masses, with his major label debut album Still Sleep? that dropped June 2021. Still Sleep? came out as #2 album on Apple Music, Top 20 on Billboard, 8 on Spotify’s US charts & has remained on the charts since June. Sleepy’s breakthrough track off the album 2055 is now RIAA Certified Platinum. At the moment, the song has garnered over 150 million streams and continues to hit new peaks week over week. Sleepy has been taking the project to the festival circuit landing Rolling Loud in both Miami & NY, Hot 97’s Summer Jam, Day N Vegas & more. Sleepy has also released Still Sleep? (Deluxe), bringing in features from Chucky73, Casper Magico, Eli Fross and Skillibeng. Sleepy & the rest of the Winners Circle crew are also set to release a joint project to rollout top of 2022.

Incorporated in 2019, Winners Circle Entertainment includes label co-owners Sheff G and Sleepy Hallow, Eli Fross and producer Great John, who handles a majority of the label’s music production. Co-owned and operated by a solid management conglomerate which is made up of Jeremy “Jerm” Soto and Karel “White” Jorge.


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