Sleepy Hallow
Sleepy Hallow is a Jamaican-born, Brooklyn-raised rapper whose melodic take on drill connects “Deep End Freestyle,” “2055” and the albums Still Sleep? and Boy Meets World.
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Latest
Sleepy’s happenings, collected from public sources, plus their backstory and Starbook, where fans write.
Known for
Overview
- Name
- Tegan Chambers
- Roots
- Born in Jamaica; raised in Flatbush, Brooklyn
- Music
- Rapper and recording artist
- Breakout
- “Deep End Freestyle” with Fousheé, 2020
- Longtime collaborators
- Sheff G and producer Great John
- Label
- Winners Circle / RCA Records
Mini bio
How it started.
Born in Jamaica, Tegan Chambers moved to Brooklyn at five and grew up in Flatbush. He told HotNewHipHop that he began by writing remixes to songs he liked. XXL traced his first recording, “Nightmare,” to a friend’s living room studio with Sheff G, followed by a SoundCloud upload.
Finding his sound.
The “Panic” records with Sheff G helped establish his place in Brooklyn drill. Their friends introduced them to producer Great John in 2018. That partnership gave Sleepy room to develop the melodic side of his music alongside the back-and-forth rapping that fans knew.
The breakout.
“Deep End Freestyle,” featuring Fousheé, brought wider attention in 2020. His 2021 debut studio album Still Sleep? included “2055.” He followed it with Boy Meets World in 2023, bringing together guests including Lil Tjay, Fivio Foreign and Marshmello.
Music fans can live with.
In his 2023 Brooklyn Magazine interview, Sleepy described recording as therapeutic and spoke about fans relating his songs to their own lives. Read This When You Wake Up followed in December 2024. On October 30, 2026, he announced Still Sleep ?? for November 13 and released “Dirty Dan.”
Creditschronological, newest first
Albums and projects
- 2024Read This When You Wake UpRecording artist
- 2023Boy Meets WorldRecording artist
- 2021Still Sleep?Recording artist; debut studio album
- 2020Sleepy Hallow Presents: Sleepy For PresidentRecording artist
Selected singles
- 2026FineLead artist, featuring Kyle Richh
- 2025LuckyJoint artist with Sheff G, featuring Bay Swag
- 2022Die YoungLead artist, featuring 347aidan
- 20212055Recording artist
- 2020Deep End FreestyleRecording artist with Fousheé
Awards
Quotes
That’s my favorite part of it all, doing the shows and being there with my fans.Sleepy Hallow, Brooklyn Magazine, September 15, 2023
On seeing fans respond to his songs at live shows. Source linked below.
Trivia
- He told Brooklyn Magazine that he only downloaded TikTok in 2023, after people had already been showing him his songs going viral there.
- In his HotNewHipHop interview, he explained that “Panic” became a series name for songs where he and Sheff G traded lines back and forth.
- His love of gaming helped inspire The Hallow Heist, the Fortnite concert experience announced in April 2025.
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