The Legacy of Sleepy Hallow

Sleepy Hallow: Sept. Hip-Hop Rookie of the Month – Billboard

Sleepy Hallow is a Brooklyn Native who gained prominence in the drill music scene. Specifically Brooklyn drill.

Tegan Joshua Anthony Chambers, known professionally as Sleepy Hallow, is an American rapper. He was born in December 19, 1999 in Jamaica. There is not much information on his family but knowing that he was born in Jamaica shows me that he must have been raised in a strict environment. He at first wanted to become a basketball player like most New York kids but he later found that his rapping skills were better than he thought. His influences range from a host of artists like Biggie Small, Drake, J Cole, and Kendrick Lamar.

Living in Flatbush, Sleepy says that there was violence all the time, and he had to keep himself tough and protected. He was hustling at a young age and eventually got picked up for cannabis possession when he was just 15 years old. This got him three months locked up in juvenile detention, and you think it would have made him learn his lesson. Instead, right when he came out, he started to get deeper into crime. Sleepy dropped out of school after 9th grade And he joined the gang the 83 Gangster Crips out of L.A. 

Sleepy Hallow’s early career involves his introduction to the music scene and the cultivation of his skills. He started gaining attention with tracks like “Sleepy Freestyle” and “Breaking Bad.” His collaboration with fellow rapper Sheff G, “Panic Part 3,” further contributed to his growing reputation in the drill music community.

The middle phase of Sleepy Hallow’s career involved continued growth in popularity and the release of more projects. He may have worked on mixtapes, EPs, or albums during this time to solidify his position in the rap scene. Collaborations with other artists and the exploration of diverse musical styles was also be part of this phase.

Sleepy Hallow’s late career saw significant success with tracks like “Deep End Freestyle” and “Molly Water.” His debut project, “Don’t Sleep,” contributed to his rising status in the rap industry. He continued to be associated with the drill sound while incorporating his unique style and flows.

During this time, Sleepy Hallow collaborated with other notable artists, and his music videos gained millions of views on platforms like YouTube. He was recognized not only for his energetic and distinctive delivery but also for his storytelling abilities within his lyrics. He most recent album has been doing numbers since it dropped. Mostly gaining a lot of recognitions due to the fact that he was recently let out of prison.

Sheff G and Sleepy Hallow to perform at New York State Fair | WSTM

Sheff G and Sleepy Hallow are close friends and pioneers of the New York drill scene; Sheff G is recognized for his songs “No Suburban” and “Weight on Me,” while Sleepy Hallow is known for his songs “2055” and “Deep End.” They eventually decided to set up their own label to both keep control of their sound and keep a larger cut of the money they were making. Enter Winner’s Circle Entertainment Named after a race they’d once seen on TV. This label is co-owned by the two rappers, together with rapper Eli Fross and producer Great John.

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