Sleepy Hallow Net Worth: How the Brooklyn Drill Rapper Built His Fortune


Sleepy Hallow is one of the rising stars in the Brooklyn drill scene, known for his unique flow and catchy hooks. With his hit singles like “Deep End Freestyle” and “Breaking Bad,” Sleepy Hallow has quickly become a fan favorite in the rap community. But beyond his music, many fans are curious about how much the young artist has made and what his net worth is. In this article, we will delve into Sleepy Hollow’s rise to fame and examine how he built his fortune.

Who is Sleepy Hallow?

Before we talk about his net worth, let’s first introduce the man himself. Sleepy Hallow, whose real name is Darryl Aaron, was born on May 21, 1999, in Brooklyn, New York. He grew up in the notorious Red Hook Houses and started making music at a young age. However, it wasn’t until 2019 that he gained widespread recognition with his single “Deep End Freestyle.” Since then, he has released several successful projects and collaborated with other big names in the rap industry.

Sleepy Hollow’s Music Career

Sleepy Hollow’s music is characterized by his distinct flow and catchy melodies. He often raps about his upbringing in Brooklyn and the struggles he faced growing up. His breakout hit “Deep End Freestyle” has been streamed over 100 million times on Spotify and is widely regarded as one of the best Brooklyn drill songs of all time. He has also collaborated with other big names in the industry, including fellow Brooklyn drill rapper Sheff G and popular hip-hop artist Lil Uzi Vert.

Sleepy Hollow’s Net Worth

So, how much is Sleepy Hallow worth? While there is no official figure available, some estimates put his net worth at around $1 million. This figure is based on his record sales, streaming revenue, merchandise sales, and concert earnings. As Sleepy Hallow continues to grow in popularity, his net worth is likely to increase as well.

How Sleepy Hallow Built His Fortune

Sleepy Hollow’s success can be attributed to several factors. First, he is an incredibly talented rapper with a unique style that has resonated with fans. His music is catchy, relatable, and authentic, which has helped him gain a loyal following. Additionally, Sleepy Hallow has been strategic in his collaborations with other artists. By working with big names in the industry, he has been able to expand his audience and gain exposure to new fans. Finally, Sleepy Hallow has been smart about monetizing his music. He sells merchandise, performs at concerts, and has even started his own record label, Winner’s Circle Entertainment.

Sleepy Hollow’s Future

With his rising popularity, Sleepy Hollow’s future in the music industry looks bright. He has already achieved a lot in a short amount of time and has established himself as one of the top artists in the Brooklyn drill scene. As he continues to release new music and collaborate with other big names in the industry, it’s likely that Sleepy Hollow’s net worth will continue to grow.


Sleepy Hallow is a rising star in the rap industry, known for his unique flow and catchy melodies. While his net worth is estimated at around $1 million, his success can be attributed to his talent, collaborations with other artists, and smart business decisions. As Sleepy Hallow continues to grow in popularity, it’s likely that his net worth will increase as well.

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