Sleepy Hallow

Tegan Joshua Anthony Chambers, known professionally as Sleepy Hallow, is a Jamaican-American rapper and singer-songwriter who specializes in Brooklyn drill. Born in Jamaica, Chambers was raised in Flatbush, Brooklyn, New York City, alongside frequent collaborator and co-founder of Winners Circle Entertainment 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 verse on the Sheff G's 2019 single, "Flow". 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.

Read This When You Wake Up - 2024-12-13T00:00:00.000000Z

Boy Meets World - 2023-09-15T00:00:00.000000Z

Still Sleep? (Deluxe) - 2021-10-08T00:00:00.000000Z

Still Sleep? - 2021-06-02T00:00:00.000000Z

Sleepy Hallow Presents: Sleepy For President - 2020-06-05T00:00:00.000000Z

DON'T SLEEP - 2019-10-31T00:00:00.000000Z

Fightland - 2025-11-06T00:00:00.000000Z

Lucky (feat. Bay Swag) - 2025-09-11T00:00:00.000000Z

Calm 3 - 2025-07-25T00:00:00.000000Z

Woke Up - 2025-06-27T00:00:00.000000Z

Girls Like Girls - 2025-04-18T00:00:00.000000Z

MARGARET - 2025-02-14T00:00:00.000000Z

Don't Sleep While It's Lit - Part 2 - 2024-11-15T00:00:00.000000Z

Don't Sleep While It's Lit - Part 1 - 2024-11-01T00:00:00.000000Z

All Mine - 2024-10-18T00:00:00.000000Z

Nostalgia (feat. Gray Hawken) - 2024-08-28T00:00:00.000000Z

Bridge In London (feat. Sleepy Hallow) - 2024-08-15T00:00:00.000000Z

Yes Freestyle (feat. Sheff G) - 2024-07-10T00:00:00.000000Z

Wildlife (feat. Sleepy Hallow) - 2024-05-24T00:00:00.000000Z

Winners In Paris - 2024-05-08T00:00:00.000000Z

Cupid's Guidance - 2024-02-14T00:00:00.000000Z

For You (feat. TaTa) - 2023-08-30T00:00:00.000000Z

GBG (feat. Marshmello) - 2023-08-11T00:00:00.000000Z

Good Girls Ain't No Fun - 2023-07-12T00:00:00.000000Z

Pain Talk (feat. Lil Tjay) - 2023-05-24T00:00:00.000000Z