“Combining drill beats with softer melodies through sampling has become [Sleepy Hallow’s] forte” – Cydney Lee, Billboard
“The rapper spits with the kind of ease and flash that starts block parties” – Alphonse Pierre, Pitchfork
“Sleepy’s lane is predicated on letting his emotions soak into his tracks and making them sink into your brain with his slippery flow” – Jordan Rose, COMPLEX
“The star-studded [Boy Meets World] sees the Brooklyn rapper looking more inward than ever before.” – Elaina Bernstein, Hypebeast
[Wednesday, July 10th, 2024]
Brooklyn superstars Sleepy Hallow and Sheff G have added another hit in their collaborative catalog with an exciting new video single, “Yes Freestyle” — out now via Winners Circle Entertainment/RCA Records. Widely hailed as one of Brooklyn’s artists to watch, the track marks Sleepy Hallow’s first release following May’s “Winners In Paris” (32M Streams) as well as February’s 112-sampling “Cupid’s Guidance” (28M Streams). An ode to 2000’s visual aesthetics and fashion, the new video for “Yes Freestyle” finds them adding to the long lineage of Sheff and Sleepy link ups, including “Tip Toe”, “Flows”, “Weight on Me”, “Breaking Bad (Okay)” and more. Drawing inspiration from pop stars like Ed Sheeran and Olivia Rodrigo as much as his early influences in Hip-Hop, Sleepy Hallow is ushering in a new era with “Yes Freestyle” (feat. Sheff G), continuing to showcase why Rolling Stone has hailed him as an artist who is “expanding the definition of drill rap.”
First exploding onto the national stage in 2020 with his RIAA Certified Platinum track “Deep End Freestyle” (600M Streams), Sleepy Hallow made his major label debut in 2021 with Still Sleep?, which charted in the Top 20 on Billboard and received praise from COMPLEX as a project that “sees Sleepy take a well-deserved victory lap.” The artist co-founded independent label Winners Circle Entertainment alongside fellow Brooklyn rap mainstay Sheff G and has continued to carve out his own lane as one of the scene’s rising stars ever since, receiving high honors from Billboard, HipHopDX, and BET as well as making appearances at Rolling Loud and Day N Vegas. Most recently, Sleepy Hallow made waves with 2023 album Boy Meets World, which featured the likes of Marshmello, Fivio Foreign, and Lil Tjay and boasted hit tracks “Die Young” featuring 347aidan (530M Streams) and “A N X I E T Y” featuring Doechii (124M Streams). With over 2.5 billion streams and 427 million video views worldwide, Sleepy Hallow is continuing to cement his name as one of rap’s breakout stars as he prepares to release even more music in 2024.
Please find links to watch and stream “Yes Freestyle” (feat. Sheff G) below and stay tuned for more announcements to come:
SLEEPY HALLOW – “YES FREESTYLE” (FEAT. SHEFF G)
WATCH | LISTEN
About Sleepy Hallow:
Over the last decade, Jamaica-born Sleepy Hallow has defied all expectations, committing to 20-hour days at the studio and relying on an innate perseverance despite the often discouraging environment around him growing up. Sleepy wrote his first rap at 14, influenced by the Jamaican music of his parents’ generation, coupled with rappers like 50 Cent, Kendrick Lamar, Drake and Childish Gambino that he would hear at home by way of his older brother. Within a few years, Sleepy catapulted to stardom alongside fellow Brooklyn native, Sheff G, with the pair founding independent label Winners Circle Entertainment. What followed was a flurry of RIAA certifications, including the triple platinum hit single “2055” and the platinum “Deep End Freestyle” featuring alternative singer Foushee, the latter landing on the Hot 100 and solidifying the rapper’s mainstream appeal. Other offerings including “Molly” ft. Sheff G, “Breaking Bad” ft. Sheff G, and album Still Sleep? have gone Gold. The album has reached festivals including Rolling Loud Miami and New York, Day N Vegas and Hot 97’s Summer Jam, among others. Winners Circle is now home to four artists, including rising acts Jay Bezzy and Eli Fross. Accomplishments considered, it’s safe to say the rapper has established his reign over the drill sound. In recent years, he scored Billboard’s R&B/Hip-Hop Rookie of the Month spot, was recognized as a HipHopDX Rising Star, a Spotify RADAR artist, and secured BET’s Amplified Artist of the Month, in addition to appearing in the BET Hip Hop Awards cypher. Now, Sleepy is setting into motion a new chapter in his career, maintaining the pulsating production of his drill roots, with a deliciously pop edge. With recent single “Cupid’s Guidance”, a melodic street symphony, Sleepy is aiming to usher in a new wave of music beyond his drill roots. Sleepy’s emerging era will be just as multifaceted as the artist himself, who reveres pop stars like Ed Sheeran and Olivia Rodrigo just as much as his early hip-hop influences. With a passion for drawing and fashion, he continues to identify left-of-center influences and samples to infuse into his discography. Sleepy’s goals for his artistry are twofold, on one end characterized by a desire for legend status, but equally, a longing to accompany fans through life’s highs and lows. With over 2.5 billion streams and 427 million video views worldwide, it’s clear that Sleepy’s vulnerable and authentic lyricism will continue to resonate with the masses for decades to come.
