Sleepy Hallow Is a New York Drill Rap Innovator

Brooklyn drill rapper Sleepy Hallow speaks about being an innovator in New York's sample drill scene, gives an update on Sheff G, and talks about his new music.

Sleepy Hallow press photo by Kirby Esquea

Photo by Kirby Esquea

Sleepy Hallow press photo by Kirby Esquea

Sleepy Hallow doesn’t shy away from illustrating the uglier sides of life in his music. He knows his fans feel empowered by seeing other people go through the same struggles as them, and he’s motivated by their responses to his songs.

“In my comments, people tell me how much I helped them through shit, and I’m always so surprised because I’m dealing with my own shit, too,” the Brooklyn-by-way-of-Jamaica rapper explains. “But there will be certain things I say where people will say it was a motivation for them. That is always motivation for me to open up more and let them know that I’m going through shit, too. Everybody’s got something going on.”

Sleepy first emerged in the New York City rap scene while working with his close friend and Winner’s Circle labelmate Sheff G. Both Brooklyn rappers took charge as leaders of the drill movement, but chiseled their own lane with a fresh approach to the sound. Sleepy turned heads with his popular mixtape Don’t Sleep in 2019, before dropping his debut studio album Still Sleep? in 2021, and establishing himself as one of the first New York drill artists to go viral by utilizing samples in his songs. 

Sample drill has become a popular sound in boroughs like the Bronx, but Sleepy Hallow’s songs like “Deep End Freestyle,” “2055,” and “Basketball Dreams” were making waves on TikTok before most of the current sample drill artists found mainstream appeal. Sleepy is quick to point out he puts his own spin on the sound: While most artists sample classic R&B songs to leverage a sense of nostalgia, he prefers obscure tracks that he finds randomly. And he harmonizes with the sample in a uniquely syrupy way, floating over melodic beats from go-to producer Great John. 

His latest single “Die Young” borrows from alternative artist 347aidan’s track “Memories!” which Sleepy came across while casually scrolling through social media. Then they connected through their management, and “Die Young” was born. “I don’t wanna die young, so I stay with a stick,” Sleepy raps, interloping the hook of “Memories!” that caught his attention in the first place. The song will arrive on his forthcoming project, which Sleepy says will incorporate vibes that appeal to the different demographics of his fanbase.

Not everything has been easy during Sleepy’s rise to success, though. Shortly after the release of Still Sleep?, Sheff G was sent to prison for two years after pleading guilty to criminal possession of a firearm. This left Sleepy without his right-hand man, but he says he had been learning to be self-sufficient as an artist in the years prior. “We always used to go [to the studio] together, so [Sheff] was growing as an artist and I was growing as an artist,” Sleepy says, explaining what it was like growing under Winner’s Circle. “Basically, we learned to be able to stand on our own as individual artists.”

Currently, Sleepy faces legal issues of his own. While details remain unclear, his Instagram page has hinted that he’s currently in jail by posting messages like “free me” in recent days. When reached for comment, his label provided the following statement to Complex: “Sleepy Hallow is currently incarcerated. Sleepy and the Winners Circle Entertainment team appreciate the support they have received from collaborators and fans during this time.”

In mid-June, we spoke with Sleepy about being an originator of the sample drill wave, a status update on Sheff G, and what fans can expect from his upcoming album.

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You’re one of the originators of sample drill in New York, and you were one of the first artists to go viral with it. How does it feel to see how much the scene has grown now? 

I was really the first one. It’s fire to see everybody express themselves on the beats. I respect it and like it a lot. When I do it, I do it differently, so I never feel like anybody is copying me or anything. I do it my own way.

Are there any Bronx sample drill rappers that you enjoy listening to right now? I saw you reposted Kay Flock’s “Shake It (Remix)” recently.

I fuck with Kay Flock and Dougie [B]. I fuck with them all, but I fuck with them more because I’ve been face-to-face with them and they’ve told me they listened to my shit before, so we were cool on that end. That don’t happen with a lot of niggas that I’ve been around. We don’t tell each other that we’ve listened to each other’s shit or fuck with it before knowing each other, so that was tough. That’s not really a thing in New York. Niggas won’t give nobody else their flowers once you blow up. Niggas aren’t going to be like, “Yo, I fuck with this shit heavy.” Even if niggas do listen to your shit, they ain’t going to be like, “Yo, I fuck with you.” It’s a New York thing.

What type of music were you surrounded by growing up, and how did that influence the samples you like to rap over?

I was surrounded by everything. My oldest sister used to listen to white people music, and I’m Jamaican so I know mad reggae. I know a lot of weird songs, but I don’t even know the names of them. I’ll hear a white ass song, though, and be like, “Oh shit, I dead know some of this shit.” I grew up on mad different shit. I choose samples based on how I’m feeling at the moment. How I’m feeling at the moment also determines which way we’re going to lean, too.

How were you feeling when you made “Die Young” and sampled 347aidan’s song “Memories!”

My feelings changed to fit that song. I was scrolling through something and watching mad funny videos, and “Memories!” was the song behind one of them. Then I listened to the regular song and was like, “Nah, this shit fire,” and decided to sample it. As I was sampling it, we just linked and got mad cool and shot the video together. It was really just the line where he said, “I don’t want to die young,” and I thought that shit was fire. I really wanted to base the song around that line, that’s why I kept repeating it so they understand.

Sleepy Hallow press photo by Kirby Esquea

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How is Sheff G? And how has your relationship been since he’s been in prison?

We’ve been chopping it up. I was talking to him right before I got on the phone with you. We talk all the time, and he’s been gucci. I’ve just been trying to keep his head up, because there’s certain shit he’s missing. I send him videos and shit, but he’s doing good, though. He’s always in good spirits. He can make a joke out of anything. 

You and Eli Fross have been holding it down for Winners Circle while he’s been away. What has been the most important lesson you’ve learned over these last two years since you really blew up?

I’ve learned that the people really fuck with Sleepy, because after I did my first song by myself, Sheff used to motivate me all the time and tell me I was the GOAT, so I just kept at it. When we made the label, we both opened up on different labels. Sometimes I would be in the studio by myself and sometimes he would be, and we never used to do that. We always used to go together, so he was growing as an artist and I was growing as an artist. Basically, we learned to be able to stand on our own as individual artists. 

What’s one critical piece of advice or lesson you learned that you would tell your younger self two or three years ago?

I would tell myself not to be afraid to thug shit out. I feel like I had my head on properly the whole time, though. Yeah, I made mistakes, but I feel like certain mistakes are what opens your eyes to certain things. I would probably just give myself more business tips, if anything. 

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