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Sleepy Hallow

  • Country Flag United States
  • Rap

Sleepy Hallow is a Brooklyn drill rapper and songwriter who has achieved RIAA platinum certifications and Billboard Hot 100 placements, establishing his presence in the music industry.

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Past Works

RCA Records

Winners Circle Entertainment, Sleepy Hallow's label, announced a partnership deal with RCA Records, increasing his distribution and reach within the music industry.

BRAND PARTNERSHIPS

Fortnite

Sleepy Hallow held an exclusive virtual concert event, 'The Hallow Heist,' within the popular video game Fortnite.

BRAND PARTNERSHIPS

Sony Music Entertainment

Sleepy Hallow is associated with Sony Music Entertainment, which distributes his news and updates through his official website.

BRAND PARTNERSHIPS

Ubiquitous

Ubiquitous, an influencer marketing agency, worked with Sleepy Hallow to elevate his presence and propel his career within the music industry.

BRAND PARTNERSHIPS

First met Sheff G and began collaborating (Early life)

MILESTONE
2017

Signed with Nula Entertainment

MILESTONE
2019

Released debut mixtape "Don't Sleep"

MILESTONE
2019

Co-founded Winners Circle Entertainment

MILESTONE
2019

Featured on Sheff G's single "Flow"

MILESTONE
2020

Released second mixtape "Sleepy for President"

MILESTONE
2020

Certified platinum by RIAA for "Deep End Freestyle"

MILESTONE
2020

First entry on Billboard Hot 100 with "Deep End Freestyle"

MILESTONE
2020

Winners Circle Entertainment partnered with RCA Records

MILESTONE
2021

Released first studio album "Still Sleep?"

MILESTONE
2022

Certified double platinum for "2055"

MILESTONE
September 2022

Released single "2 Mins of Pain"

MILESTONE
November 2022

Released single "Marie"

MILESTONE
September 2023

Released second studio album "Boy Meets World"

MILESTONE
February 2024

Released single "Cupid's Guidance"

MILESTONE
May 2024

Released single "Winners In Paris"

MILESTONE
December 2024

Scheduled to release "Read This When You Wake Up"

MILESTONE

About

Tegan Chambers, professionally known as Sleepy Hallow, is a Jamaican-American rapper and singer-songwriter specializing in Brooklyn drill. Born in Jamaica, Chambers later relocated to Flatbush, Brooklyn, New York City, where he began rapping around the age of 12. He subsequently adopted the name “Sleepy Hallow,” which was a known moniker for him in the streets. Chambers left school during the ninth grade. His career began gaining momentum in 2017 when he signed with Nula Entertainment, a music record label founded by former NFL player Junior Galette, alongside fellow artists Sheff G and DizzyGotBands. This early period established his working relationship with Sheff G, a frequent collaborator.

In 2019, Sleepy Hallow released his debut mixtape, “Don’t Sleep.” The same year, Winners Circle Entertainment was established, with Sleepy Hallow among its initial signees. His recognition expanded with his verse on Sheff G’s 2019 single, “Flow.” The following year, in 2020, he released his second mixtape, “Sleepy for President.” This project featured the single “Deep End Freestyle” (featuring Fousheé), which achieved platinum certification from the Recording Industry Association of America (RIAA) and marked his first entry on the Billboard Hot 100 chart, peaking at number 80. By August 2020, Winners Circle Entertainment formed a partnership with RCA Records, reflecting his growing commercial success.

His career continued to progress with the release of his first studio album, “Still Sleep?,” in June 2021. This album included the single “2055,” which was certified double platinum by March 2022 and reached number 51 on the Billboard Hot 100 chart. In September 2022, he released the single “2 Mins of Pain,” followed by “Marie” in November 2022. In May 2023, Chambers faced legal challenges, being charged in a 140-count indictment related to alleged gang activity. Following his release, Sleepy Hallow launched his second studio album, “Boy Meets World,” on September 15, 2023, which featured collaborations with artists such as Marshmello and Doechii. He has continued to release singles, including “Cupid’s Guidance” in February 2024 and “Winners In Paris” in May 2024.

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