WINNERS CIRCLE PRESENTS: SLEEPY HALLOW & SHEFF G

Sleepy Hallow, is a Jamaican-American rapper and singer-songwriter who specializes in Brooklyn drill. Born in Jamaica, Chambers was raised in Far Rockaway, Queens, New York City, alongside frequent collaborator Sheff G.

Signing with Winners Circle Entertainment in 2019, the label entered a joint venture with RCA Records the following year. Chambers first saw recognition for his 2019 single, "Flows" (with Sheff G). His 2020 single, "Deep End Freestyle" (featuring Fousheé) received platinum certification by the Recording Industry Association of America (RIAA) and marked his first entry on the Billboard Hot 100. His 2021 single, "2055" peaked at number 51 on the chart.

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Sheff G, is an American rapper. He rose to fame with his 2017 single "No Suburban", which was a response to the song "Suburban" by 22Gz. 22Gz response with a song titled "Retaliation", and Sheff G responded with "No Suburban Pt.2  Williams is widely known as one of the vanguards of the Brooklyn drill movement. On May 16, 2023, Williams was indicted with 31 other purported gang members responsible for several shooting incidents and at least one murder over a two-year span.