Sleepy Hallow

Sleepy Hallow
Sleepy Hallow | Source: Starsoffline

Profile Summary: Sleepy Hallow

  • Full Name: Tegan Joshua Anthony Chambers
  • Nickname(s): Sleepy Hallow
  • Birthday: December 20, 1999 🎂
  • Age: 25 years old (as of 2025)
  • Birthplace: Jamaica
  • Nationality: American
  • Ethnicity: African American
  • Zodiac Sign: Sagittarius ♐

Family Life

Parents & Siblings:

  • The identities of his parents remain undisclosed.
  • Known to have Jamaican roots, as his family moved to the U.S. shortly after his birth.

Children:

  • Daughter: Melina (from a previous relationship with Dreaa Banks ).
    • While he keeps details private, Sleepy occasionally shares pictures of his daughter on social media.

Personal Life:

  • Appears to be single as of 2025, focusing primarily on his music career and raising his daughter.
  • Maintains a private personal life, rarely discussing his dating history or romantic relationships.

Education

  • Graduated from high school in Brooklyn, New York.
  • Admits o being a smart student initially but struggled academically after spending three weeks in a juvenile detention center for marijuana possession.
  • Despite challenges, he graduated with a 2.2 GPA , expessing gratitude for completing his education.

Career Highlights

Professional Background

  • Primary Professions: Rapper, Singer, Songwriter.

Early Career:

  • Began honing his rapping skills during his teenage years in Brooklyn, New York , inspired bylegendary artists like Biggie Smalls , Kendrick Lamr , and J. Cole .
  • Collaborated closely with his best friend and frequent collaborator, Sheff G , during tis time.

Breakthrough Role:

  • Gained recognition after signing with Nula Entertainment (2017–2018) alongside Sheff G .
  • Released his deut mixtape, Don’t Sleep (2019) , which earned widespread acclaim and marked the beginning of his rise in the music industry.

Notable Achievements:

  • Music Career:
    • Followed up with the mixtape Sleepy for President , featurng the hit single “Deep End Freestyle” (featuring Foushee ), which was certified Platinum .
    • Signed ith Winners Circle Entertainment (founded by him and Sheff G ) and RCA Records , further solidiying his place in the industry.
    • Released his debut album, Still Sleep? , which received critical praise and commercial success. The album featured the hit single “2055,” certified Gold .
  • YouTube Pesence:
    • Active on YouTube, where he has amassed over 500k subscribers , sharing music videos and engaging content with fans.

Legacy in Music:

  • Celebrated as one of the most promising young rappers in the industry, known for his unique style, lyrical depth, and raw talent.
  • Recognized for his ability to blend storytelling with catchy beats, drawing inspiration from both classic and contemporary hip-hop legends.

Trivia/Facts

  • Born under the zodiac sign Sagittarius, symbolizing creativity, ambition, and optimism.
  • Of Jamaican descent, reflecting his cultural heritage.
  • A member of the street gang Eight Tray Gangsta Crips , though he focuses primarily on his music career.
  • Founded the record label Winners Circle Entertainment with his best friend Sheff G , showcasing his entrepeneurial spirit.

Legacy

Sleepy Hallow, born Tegan Joshua Anthony Chambers, is an American rapper, singer, and songwriter celebrated for his rapid rise in the music industry. Originally from Jamaica, he moved to Brooklyn, New York, as a child, where he developed his passion for rapping. Inspired by icons like Biggie Smalls , Kendrick Lamar , and J. Cole , Sleepy quickly established himself as a standout artist with his unique sound and lyrical prowess.

His breakthrough came with the release of his debut mixtape, Don’t Sleep (2019) , followed by the critically acclaimed Sleepy for President , which featured the Platinum-certified hit “Deep End Freestyle.” Signing with Winners Circle Entertainment and RCA Records, Sleepy cemented his status as a rising star in hip-hop.

In 2025, Sleepy continues to make waves with his debut album, Still Sleep? , which includes the Gold-certified single “2055.” His ability to craft relatable, introspective lyrics while maintaining a fresh and energetic style has earned him widespread acclaim.

Beyond music, Sleepy is a devoted father to his daughter, Melina, and remains active on platforms like YouTube, where he connects with fans through his creative content. As a co-founder of Winners Circle Entertainment, he demonstrates not only artistic talent but also business acumen.

Despite challenges in his early life, including a brief stint in juvenile detention, Sleepy Hallow has overcome obstacles to become one of the most exciting voices in modern rap. With his undeniable potential and growing influence, he is poised to leave a lasting legacy in the music industry. 🌟🎤✨

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