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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" received platinum certification by the Recording Industry Association of America and marked his first entry on the Billboard Hot 100. His 2021 single, "2055" peaked at number 51 on the chart. From Wikipedia (

1

2055 E

2

Weight On Me E

3

Deep End Freestyle E

4

1999 E

5

Die Young (feat. 347aidan) E

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Read This When You Wake Up

2024

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DON'T SLEEP

2019

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Boy Meets World

2023

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Still Sleep?

2021

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Sleepy Hallow Presents: Sleepy For President

2020

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Fine (feat. Kyle Richh)

Single • 2026

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Lucky (feat. Bay Swag)

Single • 2025

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MARGARET

Single • 2025

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WTW? First Day Out

Single • 2026

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Calm 3

Single • 2025

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Don't Sleep While It's Lit - Part 2

Single • 2024

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Young & Dumb

Single • 2026

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Woke Up

Single • 2025

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Baby I

Single • 2026

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Girls Like Girls

Single • 2025

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Fine (Official Video) (feat. Kyle Richh)

Sleepy Hallow • 191K views

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1999

Sleepy Hallow • 61M views

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Breaking Bad (Okay) (feat. Sheff G)

Sleepy Hallow • 27M views

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WTW? Freestyle/First Day Out (Official Video)

Sleepy Hallow • 729K views

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Die Young (Official Video) (feat. 347aidan)

Sleepy Hallow • 40M views

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Molly

Sheff G & Sleepy Hallow • 41M views

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2055 (Official Video)

Sleepy Hallow • 208M views

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Sleepy Hallow - Lowkey (Lyric Video)

Sleepy Hallow • 46M views

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Deep End Freestyle

Fousheé & Sleepy Hallow • 80M views

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ANXIETY (Official Video) (feat. Doechii)

Sleepy Hallow • 24M views

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Murda She Wrote (Live Session) | Vevo Ctrl

Sleepy Hallow • 886K views

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Round Midnight

Fousheé & Sleepy Hallow • 21K views

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Chicken (Live Session) | Vevo Ctrl

Sleepy Hallow • 482K views

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New York State of Mind

Playlist • YouTube Music

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Alt Icons

Playlist • YouTube Music

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Real Talk

Playlist • YouTube Music

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Sad Rap

Playlist • YouTube Music

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Clout Rising: New Hip-Hop

Playlist • YouTube Music

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Drill Team

Playlist • YouTube Music

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Laid-Back Hip Hop

Playlist • YouTube Music

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Spilled Emotions

Playlist • YouTube Music

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Rap Star Status

Playlist • YouTube Music

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Still Sleep? Album

Playlist • Sleepy Hallow • 4M views

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Sleepy For President

Playlist • Sleepy Hallow • 594K views

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Boy Meets World

Playlist • Sleepy Hallow • 1.8M views

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Read This When You Wake Up

Playlist • Sleepy Hallow • 412K views

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Don't Sleep Album

Playlist • Sleepy Hallow • 1.8M views

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The Black House

Playlist • Sleepy Hallow • 205K views

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Sleepy Hallow Official Video Playlist

Playlist • Sleepy Hallow • 1.6M views

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YNW Melly

17.2M monthly audience

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Melvoni

56.1K monthly audience

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CoachDaGhost

51.1K monthly audience

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Bizzy Banks

1.44M monthly audience

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MaxThaDemon

75.6K monthly audience

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StaySolidRocky

6.8M monthly audience

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Jay Gwuapo

76.9K monthly audience

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TJ Porter

79.9K subscribers

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Ron Suno

1.61M monthly audience

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26AR

115K monthly audience