★ HOW OLD IS SLEEPY HALLOW?
Sleepy Hallow is 26 years old, born December 20, 1999 in JM · Sagittarius.
#1461of 1,640 Singers on HotBirthdays
★ LEDE
About
Sleepy Hallow crafted Brooklyn drill into platinum-certified hits and chart entries. Born Tegan Joshua Anthony Chambers in Jamaica and raised in Flatbush, Brooklyn, the rapper-singer-songwriter broke through with "Deep End Freestyle" featuring Fousheé, which earned RIAA platinum status and landed on the Billboard Hot 100. He signed to Winners Circle Entertainment in 2019, co-founded by frequent collaborator Sheff G. As a Sagittarius, Chambers specializes in drill production and vocal melody.
★ FEATURE
Biography
Sleepy Hallow (Tegan Joshua Anthony Chambers) is a Jamaican-American rapper and singer-songwriter who specializes in Brooklyn drill. Born December 20, 1999, in Jamaica, he was raised in Flatbush, Brooklyn, alongside Sheff G, with whom he frequently collaborates. Chambers signed to Winners Circle Entertainment in 2019, the label founded by Sheff G and co-founder of the imprint. The following year, Winners Circle entered a joint venture with RCA Records, expanding his platform.
His breakthrough came through Sheff G's 2019 single "Flow," where Chambers' verse first gained recognition. His 2020 single "Deep End Freestyle," featuring vocalist Fousheé, became his commercial turning point—earning platinum certification from the RIAA and marking his debut on the Billboard Hot 100 chart. In 2021, he released "2055," which peaked at number 51 on the Hot 100. As a singer and rapper, Chambers blends melodic sensibilities with drill's hard-hitting production. His Sagittarius placement (born December 20) typically aligns with expansive, boundary-pushing artistry in astrology.
★ SIDEBAR
Trivia
- Chambers was raised in Flatbush, Brooklyn, alongside Sheff G, who co-founded Winners Circle Entertainment—the label that signed him in 2019.
- His 2020 single "Deep End Freestyle" featuring Fousheé achieved RIAA platinum certification, his first Billboard Hot 100 entry.
- Winners Circle Entertainment, the label that signed Chambers, entered a joint venture with RCA Records in 2020.
★ SIDEBAR
Numerology
LIFE-PATH NUMBER
Master Number — The Master Teacher
33 is 6 amplified. Caretakers operating at scale; rare among entertainers, more common among educators and activists.
★ ALL LIFE-PATH 33 CELEBS →★ ASTROLOGY
Birthday compatibility
By Chinese zodiac — san-he trine for best matches, opposing pair for the most friction-prone.
HIGHLY COMPATIBLE
- Kendall JennerPig · 1995
- Brian MayPig · 1947
- Caleb HearonPig · 1995
- Nick RobinsonPig · 1995
- Nicola PeltzPig · 1995
CHALLENGING
- Patrick MöllekenRooster · 1993
- Ewa Farna
★ FAQ
Frequently asked
- How old is Sleepy Hallow?
- Sleepy Hallow is 26 years old (born December 20, 1999).
- When is Sleepy Hallow's birthday?
- Sleepy Hallow was born on December 20, 1999.
- What is Sleepy Hallow's zodiac sign?
- Sleepy Hallow is a Sagittarius, born December 20, 1999.
- What is Sleepy Hallow's Chinese zodiac sign?
- Sleepy Hallow was born in 1999, the year of the Earth Rabbit.
- Where is Sleepy Hallow from?
- Sleepy Hallow is from JM.
- What does Sleepy Hallow do?
- Sleepy Hallow is a singer.
- Is Sleepy Hallow still alive?
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