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Sleepy Hallow
Tegan 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 (

Songs

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1
2
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Calm 3 E
3
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Weight On Me E
4
5
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Die Young (feat. 347aidan) E

Albums

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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

Singles & EPs

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Calm 3

Single2025
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Don't Sleep While It's Lit - Part 2

Single2024
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Yes Freestyle (feat. Sheff G)

Single2024
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Woke Up

Single2025
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Don't Sleep While It's Lit - Part 1

Single2024
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Winners In Paris

Single2024
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Girls Like Girls

Single2025
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All Mine

Single2024
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MARGARET

Single2025
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Nostalgia (feat. Gray Hawken)

Single2024

Videos

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

Sleepy Hallow36M views
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Sleepy Hallow - Lowkey (Lyric Video)

Sleepy Hallow41M views

Featured on

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New York State of Mind

PlaylistYouTube Music
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Alt Icons

PlaylistYouTube Music
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Laid-Back Hip Hop

PlaylistYouTube Music
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Real Talk

PlaylistYouTube Music
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Drill Team

PlaylistYouTube Music
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Spilled Emotions

PlaylistYouTube Music

Playlists by Sleepy Hallow

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Read This When You Wake Up

PlaylistSleepy Hallow332K views
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Sleepy Hallow Official Video Playlist

PlaylistSleepy Hallow1.6M views

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