If you’re looking for who starred in the Fox TV Sleepy Hollow, you’re in the wrong place. This isn’t Ichabod Crane and the village of Sleepy Hollow; this is about Sleepy Hallow rapper and singer from Brooklyn.
Sleepy Hallow is best known for his tracks “Flows,” “Panic,” and “Deep End Freestyle,” where he shows off his innovative style within the drill rap scene. But there’s a whole lot more to know about this up-and-coming music star, from his childhood to his favorite tracks.
So, let’s find out more about this artist with my in-depth look at Sleepy Hallow Rapper: Facts to Know.
Fact 1: Sleepy Hallow isn’t his real name
Yeah OK, thanks a lot. Well, just to be clear, Sleepy Hollow isn’t either. Even though it’s spelled differently, it’s still pronounced the same. This rapper was born Tegan Joshua Anthony Chambers on December 20, 1999.
That’s right; he was a Christmas baby and a millennium baby as well. He was born in Jamaica but moved to America with his family when he was still just a kid. They started living in the Flatbush area of Brooklyn, which Sleepy enjoyed.
He was nicknamed “Sleepy” as a kid, so he just slapped the “Hallow” on the end, and that was his street name which he then transitioned into rap.
Fact 2: Sleepy wanted to be a baller
From a young age, this rapper was into basketball and wanted to play professionally. Well, things don’t always work out quite as you hope, right? Things started to change in his life, two big things in particular.
First, Sleepy was living life on the tough streets of Flatbush with violence all around, and he had to grow up fast. This led him to get into trouble with the law and gangsters, too (more on that later), and away from the courts.
Also, look at the man. He’s taller than average, but at 6’2”, he’s no giant and would have to have mad skills to make it as a pro. He didn’t, but he found another way to make it instead.
Fact 3: He lived the life of a young thug for a while
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. He still appears to be a member, or at least affiliated, based on his Twitter handle @SleepyHallow83.
He was also once shot in the leg, he claims, though he didn’t report the incident as it was just part of life on the streets for him. Instead, he just manned up and kept on doing what he had to do to get ahead.
Fact 4: Sleepy got started at 12
No, not 12 am or 12 pm; I’m talking age 12. This is when he started to take a serious interest in music as an alternative road to success.
This rapper got started writing at age 12 by listening to songs and trying to write his own verses and remixes. By the time he was 15, Sleepy had released his first song, though he still wasn’t famous yet.
As a kid…
Sleepy Hallow the rapper, was listening to rap music of all kinds, focused on artists on the Young Money Entertainment label belonging to Lil Wayne. He was also into Biggie Smalls, 50 Cent, J. Cole, and even, surprisingly, Kendrick Lamar.
Plus, he was listening to both UK and Chicago Drill. You can also count Drake and Chance the Rapper as big influences on Sleepy Hallow’s early career.
Fact 5: Sleepy met Sheff G, his close friend and main collaborator, through a beef.
Back in the 2000s, teens and kids in Brooklyn would get a group together and just burst into other schools to find kids to fight with. Sometimes, they had a serious beef, but other times it was just a power play, a way to show dominance.
Sheff G, who is now one of Sleepy Hallow’s greatest friends, was trying to do just that. He had a group of around 50 kids with him, and they went to Sleepy’s school to start trouble.
Sheff G tried to call Sleepy out, but he says that Sleepy just turned around and stared him down and those 50 kids, like a total badass. Impressed, Sheff G gave him respect, and the two started a friendship after that.
And now?
Sheff G is his biggest collaborator and is also a member of the Eight-trey Gangster Crips.
Fact 6: Sleepy Hallow and Sheff G started with NuLa Entertainment
Now friends, Sheff G joined Sleepy Hallow in writing and developing their own brand of Brooklyn Drill. They ended up getting enough attention that the two young guys, now just 17 and 18, were signed to NuLA Entertainment.
This is the label created by former NFL player Junior Galette who managed them as well from 2017-2018. While they recorded some music while with this label, they left in 2018 together to do their own thing.
Fact 7: Sleepy Hallow and Sheff G own a record label
One of the more interesting Sleepy Hallow Rapper: Facts to Know is that once Sleep and Sheff left NuLa, they didn’t just sit around waiting for things to come their way. Instead, it was a calculated move.
They saw themselves working hard and the label trying to cash in on them. So, they 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.
Great John handles much of the production for the label’s releases, and the three rappers feature each other on many tracks, making this a truly collaborative community.
In 2020, even more collaboration happened when major label RCA announced they had partnered with Winner’s Circle. Sleepy put out big tracks like “Deep End Freestyle,” and his mixtapes Don’t Sleep (2019) and Sleepy Hallow Presents: Sleepy For President (2020).
Fact 8: Sleepy dropped his first full album in 2021
He had worked on lots of singles of his own and done vocals on plenty of tracks by Sheff G. But, in 2021, Sleepy Hallow’s first album, Still Sleep?, dropped, and it blew up.
This album was definitely in the Drill style…
But, Sleepy used more melodic sounds and even light guitar work, taking the hard edge off Drill and smoothing it out in a pioneering style. The single “2055” shows a sample of Drill that’s making him different from others in the Drill game. This helped him make a name for himself.
Shortly after Still Sleep? came out, Sheff G, Sleepy Hallow’s main collaborator who worked on lots of the tracks on that album, was incarcerated on a weapons conviction. Without Sheff, Sleepy was forced to continue with new collaborators.
Fact 9: Sleepy Hallow has a platinum record.
His 2020 mixtape Sleepy For President was successful, especially the track “Deep End Freestyle.” This song sold over 85 million copies and was certified Gold. Pretty good, but there was more to come. The dreamy, futuristic song “2055” off Still Sleep? was certified platinum in March 2023.
This success has got Sleepy a big name for himself and, of course, big money as well. His net worth has been estimated at anywhere between $500,000 to $3 million. Whatever it is, he has found success that few rappers ever manage to achieve.
But, Sleepy says his biggest success is when his audience connects with what he’s saying in his songs, and his lyrics help them get through the challenges in their lives.
Fact 10: Sleepy Hallow might be locked up right now
Rumors are going around that in February 2023, he got into some trouble. Apparently, police found that this rapper had a cache of several weapons, and he was arrested and then given bail.
But, in June 2023, he was sentenced on those weapons charges. There are rumors now that he will be released on February 13th or possibly 23rd, 2023.
This whole incident has been kept on the down low to the point where it’s not even clear if Sleepy’s locked up or not. But, whatever is going down, he’s off social media for now. The last thing you’ll see posted on his IG is “Free me!” so if you believe he’s in prison right now, you just might be right.
Want to Learn About Hip-Hop Styles and Artists?
If so, take a look at our detailed articles on What Is Drill Music, What Is Trap Music, Is Stan Based On A True Story, the 20 Richest Rappers In The World, and Easy Freestyle Rap Lyrics To Practice With for more information.
Sleepy Hallow Rapper: Facts to Know
Now you know more than ever about the rapper named Sleepy Hallow. More than just learning how to spell his name, you heard where he came from, how he came up hard in the streets, and how he started his career.
With friend and collaborator Sheff G, Sleepy has been making music and some big hits that got him recognized.
Right now, no one seems to be sure where Sleepy’s at, and he may be incarcerated. Wherever he is, we’re going to have to wait and see how his career will continue in the future.
Until next time, let the music play.
