10 Things You Didn’t know about Sleepy Hallow

Sleepy Hallow

Sleepy Hallow is a Jamaican-American rapper that has risen in popularity over the last couple of years, mainly because of the song ‘Deep End Freestyle’. Although he has many fans, and his fan base continues to increase, he is still relatively unknown to a lot of people. Here are ten things you did not know about Sleepy Hallow.

1. He was born in Jamaica

Sleepy Hallow, whose real name is Tegan Joshua Anthony Chambers, was born in Jamaica on December 20, 1990. However, his family moved to the United States of America when he was young. In the United States, he moved to Flatbush, a section of Brooklyn, New York. At that time, he met Sheff G, who would become his best friend and most frequent collaborator.

2. Early life

He started rapping when he was 12 years old, and his earliest influences were rappers like Biggie Smallz, 50 Cent, J Cole, and Kendrick Lamar. Early in his life, Sleepy Hallow was a very bright student and wasn’t in a lot of trouble, whether in school or at home.

He had amassed a GPA of 2.9 before he was locked up. He was sent to a Juvenile Detention Center when he was fifteen years old and was locked up for three weeks. The reason for this was because he had been caught with cannabis.

He states that after his stint in juvenile, he began to get involved in some criminal activities. His performance in school began to decline, though he did eventually get his high school diploma, with a GPA of 2.2. He does allude to the fact that it was his appreciation of freedom after being locked up that led to him being involved in what he was involved in.

3. He is a member of a street gang.

Sleepy Hallow is a member of a street gang; the Eight Tray Gangsta Crips, a gang he joined when he was released from Juvenile. His best friend and frequent collaborator, Sheff G, is also a member of the same set, and, likely, it was here where they met one another. That being said, he has never been involved in any altercations or crimes while associated with the gang and has never been to prison.

4. Drill rap

Sleepy Hallow and Sheff G were early pioneers of the drill scene that would come to be very popular in Brooklyn and the United States. They weren’t its inventors, though. The drill was a genre conceptualized in the United Kingdom. Sleepy Hallow and Sheff G, alongside other actors from the greater Brooklyn area, would import this genre, and in many ways, make it their own. They added local slag and alternate flows, creating something that was distinctively US drill

5. He was signed to Nula Entertainment.

Nula entertainment is a record label owned by the former NFL player Junior Galette. In 2017 and 2018, Sleepy Hallow and Sheff G were signed to the label. They would release some music with the outfit, but eventually, after a year, they left.

6. He has his record label.

After leaving Nula entertainment, Sleepy Hallow and Sheff G created their record label and an outfit through which they could release their music, Winners’ Circle Entertainment. By being able to own the rights to most of his music, Sleepy Hallow has amassed quite a fortune. It is estimated that he is worth over half a million dollars.

7. Debut album

In 2019, while with the record label Winners Circle Entertainment, Sleepy Hallow worked on two intense albums. The first to be released was Sheff G’s album, named The Unluccy Luccy Kid, in which Sleepy was featured seven times.

The same year, Sleepy would release his debut mixtape, Don’t Sleep. On both projects, the two artists retained their signature flow and charisma, although they did swerve away to the drill beats and setting that they had, in the past, embodied. With these two albums, though, they decided to use the trap spectrum.

8. His second project

In 2020, Sleepy Hallow released his second album, Sleepy for President. It was with this album that he was going to grow in recognition. This album did have some experimental drill styles, though guitar-driven beats were the more dominant ones.

The diverse approach he took while making this album resulted in him creating his biggest song to date. ‘Deep End Freestyle’ gained a lot of attention in the United States and the whole world.

The minimal track found international success mainly because it was trending on the social media platform Tic Tok. It peaked at number 80 on the Billboard Top 100, a list of all the hottest songs in the United States at that time, on June 20, 2020. The song has more than 85 million streams, and in August of 2020, the RIAA certified the song as Gold, meaning it sold over 500,000 million copies.

In the same month, Sleepy Hallow was signed to RCA Music, one of the biggest record labels in the world. With the label, he released the song ‘Tip Toe,’ a collaboration with Sheff G and produced by Great John.

9. New album

Sleepy Hallow announced that he would be releasing a new album, Still Sleep? On June 2, 2021. The album is the first body of work that he would be releasing with RCA Music, and Great John entirely produces it. Promotion for the album came in the form of two singles and their respective videos, ‘Chicken’ and ‘Mi No Sabe.’

The album will be released under RCA Music, as mentioned earlier, and Winners Circle Entertainment. With the success he had with his previous body of work, the album is highly anticipated and will put up some decent numbers in the least.

10. Personal life

Not a lot is known about Sleepy Hallow’s personal life, as he is a bit introverted. However, it is known that right now, he resides in Brooklyn, New York. Additionally, as aforementioned, he has a net worth of over 500,000 dollars, with some sites estimating that that number could be around 700,000 dollars. It does appear that Sleepy is a father. On social media, he often posts pictures of his daughter, Melina, whose mother is Dreaa Banks.

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