The Sleepy Hallow: A Wake-Up Call

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'Don't Sleep' is the debut mixtape from American rapper and singer Sleepy Hallow, released on Halloween 2019. Supported by the singles 2 Fake and I Get Luv, the mixtape also includes the track Dis Summah, which Pitchfork describes as cold and reflective. Sleepy Hallow, known for his collaborations with childhood friend and Brooklyn drill figurehead Sheff G, showcases his storytelling abilities and unique sound in this mixtape, solidifying his place in the Brooklyn rap scene.

Characteristics Values
Release Date 31 October 2019
Number of Songs 14
Length 33 minutes
Featuring Sheff G, ABG Neal
Producers Great John
Writers ABG Neal, Sheff G, Sleepy Hallow
Record Label Winners Circle Entertainment Inc / EMPIRE

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Sleepy Hallow's early career

Sleepy Hallow, born Tegan Joshua Anthony Chambers, is a Jamaican-American rapper, singer and composer. Born on 20 December 1999 in Jamaica, Chambers and his family immigrated to the Flatbush section of Brooklyn, New York City, when he was a child.

Chambers started rapping at around 12 years old and chose his rap name, Sleepy Hallow, from his nickname on the streets. He was influenced by prominent rappers such as Biggie Smalls, Kendrick Lamar and J. Cole. During his teenage years, he spent time honing his rapping skills and was eventually signed to former NFL player Junior Galette's music record label, Nula Entertainment, from 2017 to 2018.

In 2019, Chambers released his debut mixtape, 'Don't Sleep', under Winners Circle Entertainment, which was founded the same year with Chambers as one of its first signees. The mixtape received a lot of love and support from audiences, and Hallow began to gain recognition in the music industry. This early success led to collaborations with RCA Records and the release of his second mixtape, 'Sleepy for President', in 2020. The mixtape featured the platinum-certified hit single "Deep End Freestyle" with Fousheé, which peaked at number 80 on the US Billboard Hot 100 chart.

In August 2020, Winners Circle Entertainment and RCA Records partnered to release the single "Tip Toe", produced by Great John and featuring Sheff G. In June 2021, Sleepy Hallow released his first studio album, 'Still Sleep?', which included the single "2055". The single was certified double platinum in March 2022 and peaked at number 51 on the charts.

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Collaborations with Sheff G

Sleepy Hallow and Sheff G are close collaborators and friends, and are considered pioneers of the New York drill scene. They met in East Flatbush, Brooklyn, where they were both raised. Initially, the pair did not like each other, but they soon discovered that they had shared experiences and an organic connection. They consider each other brothers.

Sleepy Hallow and Sheff G's first collaborations were on the songs "Disrespect" and "Haters Hurtin", both released in 2017. They continued to work together on a series of singles, including "Saucin" and "Glocc wit a Sticc", and the popular "Panic" series, which became the duo's biggest hit. Sleepy Hallow was also featured seven times on Sheff G's debut album, "The Unluccy Luccky Kid".

The pair often work with Winners Circle labelmate Great John, who produces many of their songs.

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The 'Panic' series

Sleepy Hallow's "Don't Sleep" is a debut mixtape that showcases the American rapper and singer's storytelling abilities and unique sound. The mixtape, supported by the singles "2 Fake" and "I Get Luv", features collaborations with ABG Neal and Sheff G, with production by Great John. One of the standout tracks, "Dis Summah", serves as a warning, showcasing Sleepy's deep voice and reflective lyrics.

The Panic Series

The "Panic Series", consisting of "Panic Part 2" and "Panic Part 3", is a subset of Sleepy Hallow's early work, prior to the release of "Don't Sleep". This series is notable for being one of the first instances where Sleepy Hallow's talent for storytelling was recognised, a talent that would later be a key feature of "Don't Sleep".

The "Panic Series" is a narrative-driven set of songs, with each part building upon a central story. In the series, Sleepy Hallow demonstrates his skill for crafting immersive lyrical narratives, a talent that would later be honed in "Don't Sleep". The series showcases his ability to engage listeners and build anticipation, leaving them wanting more.

The "Panic Series" serves as an important precursor to "Don't Sleep", as it established Sleepy Hallow's potential as a solo artist. This potential was fully realised in "Don't Sleep", where he proved that he could, indeed, hold together a record on his own. The mixtape became a platform for Sleepy to showcase his individual style and artistic vision, free from the confines of collaboration.

The "Panic Series" represents the early promise of a talented artist, a promise that would be fulfilled in the "Don't Sleep" mixtape. Sleepy Hallow's evolution as an artist is evident, with his sound and storytelling abilities maturing and refining between the two projects. The series serves as a time capsule of sorts, capturing the raw talent and potential that would later be polished and perfected.

The "Panic Series" and "Don't Sleep" are interconnected chapters in the artistic journey of Sleepy Hallow, with the former serving as a prelude to the fully-realised world of the latter. Together, they showcase the evolution of an artist, from promising storyteller to a solo star in his own right.

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The 'Deep End Freestyle' hit

Sleepy Hallow's "Don't Sleep" is a debut mixtape released on October 31, 2019, supported by the singles "2 Fake" and "I Get Luv". Hallow, an American rapper and singer, showcases his storytelling abilities and unique sound in this mixtape.

One of the standout tracks on "Don't Sleep" is "The Deep End Freestyle", which serves as a strong representation of Hallow's artistic capabilities. The song commences with a compelling introduction, setting the tone for the rest of the track. Hallow's lyrical prowess is on full display as he delivers verse after verse with intricate wordplay and a deep, captivating voice. His flow seamlessly weaves through the instrumental, showcasing his mastery of rhythm and cadence.

The production of "The Deep End Freestyle" is meticulously crafted, with a haunting melody that creates an atmospheric soundscape. The instrumental incorporates a variety of elements, including 808s, synth pads, and subtle sound effects, adding depth and texture to the track. The mix is well-balanced, ensuring that Hallow's vocals remain at the forefront while also allowing the instrumentation to shine.

Lyrically, "The Deep End Freestyle" explores a range of themes that reflect Hallow's personal experiences and worldview. He touches on topics such as his come-up in the music industry, the challenges he has faced, and his aspirations for the future. There is an air of confidence and determination in his delivery, as he asserts himself as a force to be reckoned with in the rap game. Hallow's lyrics are honest and unapologetic, painting a vivid picture of his reality.

The release of "The Deep End Freestyle" solidified Sleepy Hallow's presence in the hip-hop landscape and garnered him well-deserved recognition. This track, along with the rest of the "Don't Sleep" mixtape, showcases his talent as a storyteller, lyricist, and performer. With its compelling lyrics, immersive production, and Hallow's exceptional delivery, "The Deep End Freestyle" has become a standout hit from the mixtape, resonating with listeners and leaving a lasting impression.

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'Boy Meets World' album

Sleepy Hallow's fourth studio album, 'Boy Meets World', was released on 15 September 2023. It is his first full-length album since 2021 and his first since emerging from prison. The album blends the New York drill style with melodic hip-hop production and pop-rap, with heavy bass-backed introspection and soul-sample head-nodders.

The album features collaborations with artists such as Doechii, Fivio Foreign, Lil Tjay, and Marshmello. One of the most popular songs on the album is "A N X I E T Y", featuring Doechii, which has been praised for its catchy chorus and the way it blends the New York drill style with a slower beat. Another popular song is "Driver's Seat (Intro)", which sets a high standard for the rest of the album with its ADHD title and New York drill style, talking about how the artist isn't afraid of confrontation.

Other notable songs on the album include "GBG", featuring Marshmello, which addresses the violence that often comes with the New York drill scene, and "Die Young", featuring 347aidan. The album also includes "Good Girls Ain't No Fun", "BWV" featuring Fivio Foreign, "For You" featuring TaTa, and "Pain Talk" featuring Lil Tjay.

The album has been well-received, with critics praising Sleepy Hallow's ability to handle the show by himself, blending his drill roots with melodic pop-rap and heavy bass. The album's runtime is 43 minutes, and it contains 18 songs, 8 of which are features.

Frequently asked questions

Halloween, 2019.

It is unclear which song is the most popular, but "Dis Summah" is described as "a must-hear rap song".

ABG Neal and Sheff G.

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