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Sleepy Hollow Rapper: 11 Facts To Know

Getting into Sleepy, aren’t we? Well, I got you! Who wouldn’t be interested in someone whose music is mainly created by him and the Great John? From the trend of his single Flows to 2055, we can break free into a list of powerful yet soothing kinds of hip-hop playlists.

Rapper Sleepy Hollow cuts straight through the melodic beats’ addictive rhythms. But don’t worry, despite its calming beat, his music will never put you to sleep! To know more about Sleepy Hollow, we got a list to slide in fast!

Sleepy Hollow Rapper


11 Facts You Didn’t Know About Sleepy Hollow


1. Life in General

Sleepy Hollow, was born in Jamaica
Sleepy Hollow was born in Jamaica

Tegan Joshua Anthony Chambers, better known as Sleepy Hollow, was born in Jamaica on December 20, 1999. He was raised in the American neighborhood of Flatbush, which is part of Brooklyn. It is known that Sleepy Hollow still resides in the Brooklyn neighborhood where he once said that staying there was “lit”. Lastly, Melina is the name of the daughter Sleepy Hollow has with Dream Banks.


2. Persona in Early Streets

When Sleepy Hollow was 12 years old, he first began to dream of becoming a rapper. Sleepy Hollow still attended junior high school at this age and wanted to continue playing basketball. But he eventually gave up on the thought because he wasn’t able to balance studying and extracurricular activities.

Expert Tip: While working on the streets to support himself, he began his musical career.


3. Named Duo, Sheff G

Sheff G had become Sleepy Hollow’s collaborator in music
Sheff G had become Sleepy Hollow’s collaborator in music

Now that the rapper’s journey had begun, he had met Sheff G, a young man who had a significant impact on his life in both childhood and musical development. How these two became rivals in the first place is truly unbelievable. The typical teenagers you see that constantly fighting with their fists, you can imagine them like that.

But well, not really. Because it was mostly Sheff G that describes the trouble when they are younger. To continue, Sheff G had become Sleepy Hollow’s collaborator in music. The tracks that they released were titled Disrespect and Haters Hurtin’ in the year 2017. The duo’s single Flows in 2020 became a viral hit.


4. Sleepy Hollow ft. Flows

When Sleepy Hollow was a teenager, he and Sheff G started getting into trouble together as his focus on school started to falter. At the age of 15, Sleepy Hollow was taken into custody for three weeks after being found in possession of marijuana by the authorities. Additionally, it was claimed that a gang member shot him after they let him go.

While Sleepy Hollow was shot in the leg, another young man with him was killed by gunfire.


5. Hollow’s Inspiration

Sleepy Hollow has been practicing his rapping skills by listening to various genres
Sleepy Hollow has been practicing his rapping skills by listening to various genres

Given that his second name sounds like Halloween, Sleepy Hollow lightly spelled it. Sleepy Hollow has been practicing his rapping skills by listening to various genres of music ever since he was 12 years old. He then pays attention to how many lyrics are sung in a given period as he listens.

It’s amazing how he gains an understanding of how it was done by doing that


6. Beats That He Grew Up In

Sleepy Hollow grew up listening to everybody’s song, but it is most likely from Drake, Kendrick Lamar, J. Cole, and Chance the Rapper.


7. Way of Producing Like 2055

The song 2055 is Sleepy Hollow’s another viral hit from his album Still Sleep? This song’s message is about living away from everything. It is about running away from the entirety of the present and living in a future where you can be whoever or whatever you want to be.

Unimaginable as it is, Sleepy Hollow did not even write a single soul of this song to make the feeling. He just took in the melody and beat from the record and then sang his rap to the record.

Expert Tip: According to him and his label, Sleepy Hollow doesn’t write his lyrics to create his song, instead, he just raps the lyrics while staying on the beat with Great John’s melody, his producer.


8. Signed Headquarters

Sleepy Hollow and Sheff G signed with Nula Entertainment as their first record company. However, they both left the label after a year. In August 2020, both of them got a deal from a major label named Winners Circle Entertainment which is a management company by RCA Records.

In collaboration with Sheff G, he released the Great John-produced song “Tip Toe”, under his current label.


9. Favorite on Beats

And now is the time to discuss his personal favorites! The song Pray 4OR from his album DON’T SLEEP, is his favorite because, in his words, it captures the process of him going through everything. He also recognizes Breaking Bad as his favorite MV because it was so easy to film and felt like a natural extension of him. To end the list, Sleepy Hollow’s favorites may be anything but chocolates!


10. Music’s HIT

Sleepy Hollow made his name through a mainstream audience with his song “Panic”. Then, with his song “Deep End Freestyle”, a single released in the year 2020. He made his first chart success. This success was followed as he released the production of his studio album in 2021 named Still Sleep?


11. Production of Albums

Sleepy Hollow worked on two significant projects in 2019. The Unlucky Lucky Kid by Sheff G was the first album on which he made seven appearances. After finishing this project, he released Don’t Sleep, his debut mixtape.

Then the mixtapes of Sleepy for President and The Black House, both of which were released as follows-ups to his first mixtapes, are still connected. Following that, Sleepy Hollow began his studio album ‘Still Sleep?’. In 2021 with his hit single, 2055. In 2022, Sleepy Hollow made a comeback to his song “Die Young.”

Now, let it all shoot in! Because of this list, we not only knew about Sleepy Hollow’s preferences but also knew and understand more about him through his journey in life.

As enthusiasts of his music, we were able to appreciate his music more by learning about his life’s journey, the people he has met, how he makes music, and how he has pursued his dreams. A note to remember: Let’s not Die Young.

About Jayden Buckley

Hi, my name is Jayden and I am author/editor for PlayTheTunes. I remember the first time I hopped on the drums, I was hooked. Music has played an enormous part of my life, and I'm honored I get to share my experiences with you!