Sleepy Hallow Biography: Age, Parents, Siblings, Songs, Net Worth, Height, Girlfriend, Instagram
Tegan Joshua Anthony Chambers, known professionally as Sleepy Hallow, is a Jamaican-American rapper and singer-songwriter who has carved out a highly influential career identity as one of the definitive pioneers of the Brooklyn drill music movement.
He is widely recognized for his dark, melodic flows and gritty street lyricism, capturing massive global attention with his breakthrough multi-platinum single “Deep End Freestyle” and cementing his stature as a cornerstone voice in the contemporary East Coast hip-hop landscape.
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| Real Name: | Tegan Joshua Anthony Chambers |
| Stage Name: | Sleepy Hallow |
| Born: | December 20, 1999 (age 26 years old) |
| Place of Birth: | Jamaica |
| Nationality: | Jamaican-American |
| Height: | 1.73m |
| Parents: | Mr. and Mrs. Chambers |
| Occupation: | Rapper and singer-songwriter |
| Net Worth: | $3.5 million |
Early Life and Education
Sleepy Hallow was born on December 20, 1999, in the Caribbean nation of Jamaica, to his parents, Mr. and Mrs. Chambers.
He spent his early childhood years under the tropical sun before immigrating with his family to the United States, growing up in the dense urban landscape of the Flatbush section of Brooklyn, New York, alongside an unidentified group of neighbourhood siblings.
The developing creative found an early affinity for music while navigating the local school system, ultimately dropping out of high school in the ninth grade to focus fully on the street dynamics that inspired his early rap verses.
Reflecting his cultural heritage and geographical upbringing, he is of Afro-Jamaican ethnicity and was raised practicing the Christian faith.
Career
Sleepy Hallow initiated his professional journey in 2017, collaborating closely with local Brooklyn icon Sheff G and securing early recording entry points through Nula Entertainment.
Navigating the legal issues and intense regional turf battles that frequently plagued the early pioneers of the Brooklyn drill scene, he channelled these harsh realities into a string of underground anthems, building a massive local buzz.
His definitive breakthrough arrived with the release of his acclaimed 2019 debut mixtape Don’t Sleep, which officially brought him widespread national recognition and laid the blueprint for his distinctively melancholic style of drill music.
Sleepy Hallow engineered massive career growth and global industry influence after co-founding Winners Circle Entertainment and securing a lucrative partnership with RCA Records.
His artistic transition culminated in the 2020 smash hit “Deep End Freestyle,” a viral, platinum-certified track that showcased his brilliant ear for sampling, which he followed with successful studio albums like Still Sleep? and his 2024 project Read This When You Wake Up.
Beyond individual charting triumphs, his creative output has fundamentally shifted the sonic direction of East Coast rap by infusing raw drill drum patterns with melodic R&B sensibilities.
His enduring legacy remains anchored in his ability to elevate a regional underground sound into a globally respected commercial force.
Social Media
- Instagram Handle: @sleepyhallow
- Facebook Handle: @SleepyHallowOfficial
- Twitter Handle: @SleepyHallowBK
Personal Life
Sleepy Hallow, born December 20, 1999, is 26 years old.
He was famously linked in the media to a Brooklyn native named Dream Banks in 2018, with the pair frequently sharing digital glimpses of their companionship across social channels without ever explicitly confirming their formal relationship status to the public.
The couple quietly drifted apart around 2020, and he has since kept his domestic affairs entirely private, listing no current marriage or public partners while remaining childless.
Discography
- 2019: Don’t Sleep (Mixtape)
- 2020: Sleepy for President (Mixtape)
- 2021: Still Sleep?
- 2023: Boy Meets World
- 2024: Read This When You Wake Up
Net Worth
Sleepy Hallow commands an estimated net worth of $3.5 million.
His foundational financial revenue is driven directly by massive streaming royalties generated from his chart-topping digital catalogue, heavily anchored by the multi-platinum certification of “Deep End Freestyle” and “2055.”
Highly lucrative international touring schedules, premium booking fees, and executive profits from his ownership stake in Winners Circle Entertainment further strengthen his financial portfolio.
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