The Life of The Brooklyn Nightmare, Sleepy Hallow

What up gang. Back with the real you know what’s the deal. Brooklyn Drill has become an epidemic that had the music industry in a chokehold with the late legend Pop Smoke

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Now that he’s gone, there comes the rise of another to evolve the Brooklyn sound straight from the shadows where he haunted the opps. The Nightmare Sleepy Hallow. A savage who when he gets shot, tells the opps to shoot him again. He went from upping the heat in the streets 

to dropping heat on the beat

But it turns out industry fame may not be enough to hold back his ways from the trenches and it may have cost him his freedom. This is a deep dive into the life of The Brooklyn Nightmare Sleepy Hallow. Let’s chop it up and break it down.

Born in the Caribbean in the island of Jamaica, Tegan Joshua Anthony Chambers aka Sleepy Hallow moved to the US with his family to pursue a better life. 

The area they chose to call their new home was known for its Caribbean influence, Flatbush. 

Sleepy Hallow as a youngin had hoop dreams, but in order to play, his grades had to be A1 and Sleepy couldn’t keep get them to where they needed to be. By high school basketball was a thing of the past https://youtu.be/9fZBkh4xSec (1:23-1:38)

Ball was a wrap, but soon another passion caught Sleepy’s interest, hip hop. From an early age around 11 he was already exploring all kinds of music. Since then its like he just knew he wanted to be a rapper, but wonder if he knew he would become as big an artist as he is now. Sleepy even tho aws so young was dissecting bars and studying the craft to a T https://youtu.be/9fZBkh4xSec (2:17-2:27)

Aight so bet, he found the path he wanted to follow. But getting there would take a couple detours and nearly never happened with the lifestyle he got caught up in. Flatbush molded Sleepy as a youngin and when he linked up with another young savage, there was no stopping the duo. That kids name was Sheff G

But their brotherly friendship didn’t start on off on the right foot. Back then Sheff G was putting paws on kids in different schools. Bro was touring but with a different kind of beats. Turns out he spotted Sleepy Hallow and that was his next target to give a concussion, but Sleepy wasn’t the one. 

He stood on business when Sheff and bout 50 goons was taunting him, and that made Sheff realize that homie was on the same type of timin he was on. From then on they were like best friends ushering in a new era for the trenches of their generation https://youtu.be/EGcjVLwiXko (6:30-6:50) https://youtu.be/t5EMbbiZE_w (2:57-3:47) 

https://hiphopdx.com/news/id.59496/title.sheff-g-recalls-planning-to-jump-sleepy-hallow-but-his-ice-glare-turned-them-into-brothers

The two was a problem and they couldn’t be stopped. Sleepy Hallow fell deeper and deeper into the hands of the trenches, growing closer to becoming a thoroughbred in the streets. By age 15 he would start being affected by the legal side of things when he was hemmed up for some mary jane and spent about 3 weeks in a juvenile detention center. It’s wishful thinking to hope bro would have learned his lesson, but for a kid like Sleepy, he just became more thuggin. He went even further down the rabbit hole, becoming affiliated with the crips that he shouts out in his songs https://youtu.be/jma9h7GgQSk (1:14-1:25) Whether in the studio or the streets, Sleepy moved with a couple crips around him in the squad https://youtu.be/KEOsdKTQO7M (3:20-3:34) https://youtu.be/R9fQ1F1Vqp4 (0:15-0:35) 

Sleepy Hallow and Sheff G continued applying pressure in the streets and dropping music. The first song they worked on together and realized they clicked on the beat was their old SoundCloud track, “Nightmare” https://youtu.be/qGqpYRI7YP4 https://youtu.be/PfdgG2iB1sE  (9:26-9:48) One of their mans got a studio session and told em slide through. That’s when they released their first official track “4 Them Racks” The energy and vibe was crazy and their homie pushed them to stay focused on rap https://youtu.be/N6i8Rp12cqM (4:39-5:07) https://youtu.be/9-ROXHQk-BU Sleepy and Sheff lived the same struggles, experienced the same heat in the streets, so the vibe was just authentic and they capitalized off that telling their story on wax https://youtu.be/EGcjVLwiXko (5:44-6:06)

At that time they were on the drill wave, gritty, aggressive, coming at their opps tops, pause. You can hear the gang influence in Sleepy Hallow bars on the song “Disrespect.” It was so early in their career he was still going by an earlier alias Sleepy ZZ https://youtu.be/baIpDtZTfOY (2:29-2:54)

Around that time Sleepy and Sheff were tryna build their music career, many didn’t know they were really out there grinding. Between 2017-2018 they were down bad. Sleepy Hallow was at his lowest. They were going nowhere, just tryna make it someway somehow. Dudes were to the point they were sleeping in the car, but no matter if they were trapping or banging to make it out, they knew they wanted something bigger in life and always ended the night putting in work at the studio https://youtu.be/9fZBkh4xSec (4:50-5:11) Sleepy Hallow and Sheff G were brothers fr, through think and thin they kept it pushing not leaving neither behind

What made things worse is Sleepy Hallow wasn’t out of the streets, he was still thugging it and a wild lil dude for real. Bro was running down on opps after they mouthing off online but the opps were tucking tail and using their shawty’s as shields https://youtu.be/QxPLRhz1flw (0:04-0:15) https://youtu.be/QxPLRhz1flw (1:10-1:37) Sleepy was a humble dude but he was ready to catch a body at any given time if dudes kept actin like they bout it. His name was known for getting active https://youtu.be/QxPLRhz1flw (1:52-1:56) Sleepy Hallow didn’t care, he would proudly disrespect his rivals and stood on it, something that could go very wrong if he was to be caught lackin https://youtu.be/QxPLRhz1flw (2:06-2:13)

That’s exactly what allegedly happened in February 2017 when the opps pulled up, hopped out the whip and aired out the strap https://youtu.be/CCNXaKEFdI4 (10:15-10:40) Luckily Sleepy hallow was wounded but not murked, but a 15-yeard-old youth by the name of Rohan Levy 

was hit in the head and passed away while his friend was also hit but survived https://youtu.be/CCNXaKEFdI4 (10:41-10:51)

https://nypost.com/2023/02/01/teen-busted-upstate-in-shooting-of-boy-15-in-nyc-cops/

https://pix11.com/news/local-news/brooklyn/15-year-old-boy-dies-from-gunshot-to-the-head/

Police officers would host a conference in an indictment about 2 years later with the arrests in multiple gang members and stated that the shooters took the boi for an opp named Sleepy Hallow which leaves the question, was Sleepy Hallow actually there and got shot, or was the boy alone mistaken for Sleepy and got shot? But, looking closer at the news, check this out. It said one of the slain teen’s friends was hit in the leg but the friend was unidentified. The only information they got was that he was 18 years old. Around that time Sleepy Hallow would have been around that age 17/18, so what if the person who got shot in their leg was Sleepy Hallow but he simply told the cops they mistook his friend for Sleepy Hallow. Remember at that time Sleepy wasn’t big in the music game as yet, so the cops wouldn’t be able to pin point his face. That’s just one theory of mine, but hey, it could be.

Either way for them to specifically name Sleepy Hallow as the target says a lot cause how did they know to make that connection? https://youtu.be/CCNXaKEFdI4 (10:55-11:04) But, check this next thing out. Sleepy Hallow would confirm he was shot, later in him and Sheff G’s viral 2019 track “Flows” https://youtu.be/DYTxB_-ysns (2:22-2:25) In a Genius lyric breakdown video here’s what Sleepy Hallow had to say about the lyrics https://youtu.be/_BQEGn9rUFg (4:03-4:17) Sleepy got hit but bro was still standing ten toes down. But, something had to give because that’s no way to live. He was tryna make it out the hood not lose his life there.

Him and Sheff got to the point where they was building a buzz and caught the attention of former NFL player Junior Galette 

Opportunity was about to knock. Galette owned his record label NuLa Entertainment and signed em to the label for a period of 1 year before they left to do their own thing

By now their drill sound had placed them in the spotlight, but Sleepy Hallow and Sheff never considered themselves just drill artists but wanted to make music, good music, global music https://youtu.be/9fZBkh4xSec (5:46-5:59) Sleepy Hallow would channel a different vibe, easing off the gritty drill sound, and bringing a more melodic smooth style. He kept the authentic street experiences but it just felt like he transitioned into that international sound he always wanted to make. You can hear the trendy vibes in tracks like “Deep End” https://youtu.be/jma9h7GgQSk  “2055” https://youtu.be/y1xZ_kAhjMc  and “2 Sauce” https://youtu.be/H1LZth0FKLM

Somewhere in the mix with all the growing success, Sleepy Hallow ended up in the hospital for a surgery. No idea what it was but it didn’t seem serious because bro went on live when he woke up and was high as a kite off the anesthesia. Bro was a one man comic stand up at that point https://youtu.be/uFbSJ7RdHk8 (0:45-1:04) https://youtu.be/uFbSJ7RdHk8 (1:21-1:35) https://youtu.be/uFbSJ7RdHk8 (1:41-1:57) https://youtu.be/uFbSJ7RdHk8 (2:10-2:34) https://youtu.be/uFbSJ7RdHk8 (4:07-4:50) https://youtu.be/uFbSJ7RdHk8 (5:45-6:17) https://youtu.be/uFbSJ7RdHk8 (6:30-6:50) https://youtu.be/uFbSJ7RdHk8 (6:44-8:14) https://youtu.be/uFbSJ7RdHk8 (8:38-9:48)

Sleepy Hallow was having fun in life, finally. With Sleepy Hallow and Sheff G finding that global voice, they decided to take it to the next step and linked with Eli Frost to partner with industry giant RCA Records to launch their own record label “Winners Circle Entertainment” 

Sleepy Hallow and Sheff G were now bosses. While other rappers are getting signed, they signed themselves to their own label maximizing profits https://youtu.be/bjrdFMrMaUE (0:24-0:53) https://youtu.be/BpjNB0lXXA8 (7:33-8:25)

Sleepy Hallow nem were up and flossing, racked up, stacked up, pulling up to the lot with the team copping new benzes cash, they finally did it https://youtu.be/maVQrSB3t6I (4:06-5:00)

Still, they wasn’t done leveling up. Sleepy nem went on to buy their own student ready to trick it out with different rooms and turn it into their official recording spot while still with ambitions to take their label to the big leagues https://youtu.be/9fZBkh4xSec (8:11-8:24)

Sadly, on their way to the top, they were met with some setbacks. Sheff G got hemmed up by the law and was sentenced to 2 years after pleading guilty to criminal possession of a weapon in November 2021

https://www.complex.com/music/sheff-g-sentenced-2-years-in-prison-pleading-guilty-criminal-possession-of-weapon

Sleepy Hallow had to hold down the fort without his best friend https://youtu.be/9fZBkh4xSec (4:12-4:49)

When it rains, it pours. Next thing we know, around June 2022, not long after filming the music video for his track with Fredo Bang “No Love” 

Sleepy Hallow shared a IG story saying Free Me https://youtu.be/Mgd0lZOwJ7c https://youtu.be/JdzpNpS3q_M (1:23-1:31)

Eli Frost his Label partner posted shouting out free the guys confirming Sleepy was picked up

A video would soon surface online that may have been why he was booked. The vid shows Sleepy wilding in a restaurant area throwing chairs and everything in a brawl with his entourage and the employees https://youtu.be/rN6GWKv7m8A A tweet from what appears to be a friend of one of the people assaulted shared text messages stating what allegedly happened. According to them, Sleepy and his grew pulled up demanding to have their meals quick time because they the richest people there. The texts shared also stated cops pulled up and arrested Sleepy

Court documents would be revealed showing he was locked up on June 2th 2022 which also exposed that he was also convicted on 1^st February 2022 and being sentenced for a criminal possession of a weapon according to the document 

VladTV also confirmed the weapons charge sentence https://youtu.be/JdzpNpS3q_M (1:33-1:45) The release date was set for 13^th February 2023 which turned out to be true cause around that time Sleepy Hallow was set free https://youtu.be/BhJtgR2UPBE https://www.youtube.com/shorts/DTySfF4hoWY https://youtu.be/AJGAVh8E4_o 

Sheff G is suppose to be home soon too, so the dream team will be back together to dominate the game. To date Sleepy Hallow has a catalog of bangers through his projects “Don’t Sleep”

“Sleepy For President”

And “Black House”

“Still Sleep?” and “Still Sleep” (Deluxe)

All he has to do now is try stay out of trouble and the world is his playground. Sleepy been through things that made his heart turn cold https://youtu.be/HoDfyXWf2lg (1:09-1:17) but he thugged it out and now, his online following went from 45k on IG in 2019

To now nearing a 1 Mil in 2023

So there you have it. Thanks for kicking it with yah boy, appreciate the love and support. Catch ya’ll in the next one. Peace up and peace out.