The Break Presents – Sleepy Hallow

There’s an authenticity in being a rising rapper who grew up in New York City, a region with a rich hip-hop history. The success to get to the point of recognition feels like a dream until experience leads the way, as is the case with Flatbush, Brooklyn rapper Sleepy Hallow. A boss with his Winners Circle Entertainment team and RCA Records artist, his sound is moving far beyond his borough with two platinum records in the bag.

Sleepy came up in the BK streets with his close friend and fellow rhymer Sheff G. On the music side, Sleepy had been making his own music since he was 12, writing verses and creating remixes to songs he heard on the radio. Releasing his first song when he was 15, Sleepy relied on the support of his friends to push him forward with his music; they played his songs everywhere they went. Surprisingly, Sleepy didn’t really think he could go anywhere with rap.

He had been recording tracks with Sheff G since 2016, and most of Sleepy’s early catalog consisted of collaborations between the two. The “Flows” and “Panic” series and later on “Tip Toe,” among other songs, showcased their own Brooklyn drill sound. By 2019, his mindset changed. Sleepy dropped his debut album, Don’t Sleep, that year, and took notice of how much fans liked him on the merit of the music he made by himself. It was then he felt a rap career was viable.

On the come up in 2019, Sheff G and Sleepy also formed the indie label Winners Circle Entertainment. Artist Eli Fross and producer Great John, who handles a majority of the label’s music production, are part of the team. With their very own label and making a name within drill circles and beyond, Sleepy was becoming one of the hottest young rappers in the city.

He’s a talented rapper known for his street savvy bars and flows that can stop and turn on a dime. Sleepy’s music also showcases a vulnerable side, one in which he doesn’t shy away from expressing his innermost thoughts. Last year, the up-and-coming rhymer was the center of attention for “Deep End Freestyle” featuring Fousheé, a hit he created during the pandemic. The track finds Sleepy rapping over singer Fousheé’s 2020 song “Deep End” with his thick Brooklyn accent and BK drill energy. “Aight, I could get you wrapped up like a gift/Smoked up like a spliff/Choppa tell ’em back up, or get hit/Got my racks up, now I’m lit,” he rhymes.

The song, which hit No. 80 on the Billboard Hot 100 last year, earned him his first platinum record. “Deep End Freestyle,” with over 197 million Spotify streams, appears on his 2020 project, Sleepy Hallow Presents: Sleepy For President.

2020 was a big year for both Sleepy and the home team. Winners Circle announced they partnered with RCA Records in August of last year, which only made things even more real for Sleepy. From there, he kept the music coming, including his own tracks as well as collabs. The business-minded artist was thinking bigger than a regional sound, crafting songs that could command an audience ready to listen.

This year, Sleepy delivered the project Still Sleep?, home of his second platinum-selling song “2055.” The dreamy viral hit—with a later addition of Coi Leray—climbed to No. 50 on the Hot 100 this year, and perfectly primed him for his next step. He’s fresh off the release of the deluxe edition of Still Sleep, and has more in store.

Fully confident in his own talents and flying the Winners Circle flag—Sheff G is currently incarcerated due to a felony gun charge—Sleepy Hallow’s music is going far past the borders of Brooklyn, and his forthcoming 29-city tour will only brighten his light. No one’s sleep now.

Age: 21

Hometown: Jamaica-bred, Brooklyn-raised

I grew up listening to: “Everybody to be honest, but main people, Kendrick Lamar, Drake, Chance The Rapper, [J.] Cole.”

My style’s been compared to: In the beginning, hell yeah. They used to be like me and Sheff [G] reminds them of Bone Thugs. I’m like nah, what the fuck? Mad shit. I’m like, nah, that’s some next shit. I kept seeing people say it here or there. That’s why I remember that one. That’s crazy. I guess they say it’s because of the flow, because in the beginning, we was going crazy with the drill.”

I’m going to blow up because: “Everything I did, honestly. How far I came, there’s no point in stopping. You done did so much! You did that much, you can do better than that. That’s how I feel.”

What’s your most slept-on song, and why?: “I feel like people sleeping on me, period. That’s for them to figure out, but a specific song though? I don’t think so.”

My standout records to date have been: “‘2055’ and ‘Deep End.’ [‘2055’] has a lot of meaning to it. [‘Deep End’] is just different. In the pandemic, I don’t know what was going on with everybody. I think it was me freestyling on a sample. That shit was different for everybody. Everybody doing that same shit now though, and I inspired them!”

My standout moments to date have been: “Going platinum. That’s shit I used to see when I was younger, and I ain’t never used to understand, like what the fuck, you went platinum? When shit like that be happening, I be looking like I’m not hype, but in my head I be happy. I be proud of myself! I got the text, ‘Yo, you went platinum, boy!’ I was like aight, bet, let’s work.”

Most people don’t know: “I taught, what’s his name? Young boy, Michael Jordan? Yeah, I taught him how to ball.”

I’m going to be the next: “The first to do something great, musically. I don’t know what it is, but I’ma be first to do it.”

Follow Sleepy Hallow on SoundCloud and Instagram.

Standouts:

“Deep End Freestyle” featuring Fousheé

“2055”

“Luv Em All”

Still Sleep? (Deluxe)