Sleepy Hallow has been smiling a lot more lately.
The normally stoic Brooklyn drill rapper walks into the Complex studio with a grin on his face. He’s finished his upcoming sophomore album, Boy Meets World. This is the first time Sleepy has been able to talk about new music since he was released from prison earlier this year after serving eight months for weapons possession, and his excitement about this next chapter of his career is palpable.
Sleepy Hallow is one of the originators of the Brooklyn drill scene, working alongside his close friend Sheff G to form Winners Circle and standing at the genesis of sample drill back in 2019. Sleepy’s debut album, Still Sleep?, helped him burst onto the rap scene and set himself apart from artists like Sheff and Pop Smoke thanks to his syrupy delivery and unique beat selection, courtesy of Winners Circle labelmate and producer Great John.
“Figure out your own flow,” Sleepy says when talking about how he separated himself from similar-sounding artists in the drill scene. “That’s how I think I started to go up. I would sit in the studio and figure out my flow and perfect my craft. I’m still working on it, but I feel like I found my own lane.”
After Sheff G was arrested in 2021 for criminal possession of a weapon (he remains in jail to this day on racketeering charges), it was up to Sleepy to keep pushing Winners Circle forward and develop his own sound. Sleepy’s lane is predicated on letting his emotions soak into his tracks and making them sink into your brain with his slippery flow. Boy Meets World has much of what made the Brooklyn rapper compelling in the first place, like a smooth SWV sample on “BWV” with Fivio Foriegn, or going back and forth with fellow melodic rapper Lil Tjay on “Pain Talk.” Sleepy is also still tapped into the continued evolution of drill, despite being locked up for nearly a year.
“I named the song ‘Cash and Chow’ because they inspired the production,” Sleepy says of fellow drill rappers Cash Cobain and Chow Lee. “I’ve definitely been tapping in. I’m supposed to get some beats and do a song with them. I heard their [music] in jail. They played that shit on the radio, and I was like, ‘Na, these niggas going crazy.’”
The trials and tribulations that Sleepy Hallow has overcome in the last few years are reflected in the album’s title as well. He smiles now because he’s been able to put life in perspective and recognize what’s important to him.
“The title [means] exactly what the title says,” he explains. “It’s a reality check. It’s me understanding life, my perspective, and my understanding of it. Everything I've been through, everything upcoming, the past. It’s just a big-ass reality check.”
We talked to Sleepy Hallow about his sophomore album, Boy Meets World, why New York drill is becoming too repetitive, and a status update on Sheff G.
How was your first Rolling Loud performance back?
I was dying to do that shit because they booked me when I was locked up, but we told them I was gonna be home for it. That’s all I’ve been thinking about since I came out. They cut my shit short though—I guess their schedule was fucked up, but it was still good though.
You have a knack for linking with collaborators outside of rap, most recently Marshmello for “GBG.” What made you want to work with him on that track?
Sometimes I don't even be looking for it. Sometimes it be finding me. I’ll hear the sound, and be like, “Oh, is fire. I could turn this shit.” And after I do the song, because you got to reach out to the people who make the song, because I just be knowing the voices. I’m like, “Oh, who is this?” Then I find out who it is, like, “Oh shit. I know.” I don't know you personally, but I know of you. Marshmello was fucking with us. He locked in, I’m not even going to lie.
What genres do you like to listen to the most other than rap? I feel like your taste is all over the place.
I be listening to Ed Sheeran and shit. [“Shape of You”] is fire. Ed messes with hip-hop. I might have to sample his shit and see what’s going on. If he’s jacking me then I jack it.
Outside of Sheff G, who do you enjoy working with the most?
I don’t collab with a lot of people, but probably [Lil] Tjay. We got a lot of other shit too. We got “Pain Talk” and me, him, and Sheff [G] got a song we did a couple years ago.
I thought it was dope how you shouted out Cash Cobain and Chow Lee on a track too. What’s your relationship with them like?
I named the song “Cash and Chow” because they inspired the production. I’ve definitely been tapping in. I’m supposed to get some beats and do a song with them. I heard their [music] in jail. They played that shit on the radio, and I was like, “Na, these niggas going crazy.”
What made you go with the title Boy Meets World? Have you ever watched the show?
The title [means] exactly what the title says. It’s a reality check. It’s me understanding life, my perspective, and understanding of it. Everything I've been through, everything upcoming, the past. It’s just a big-ass reality check. I had the title for mad long; I was just iffy on it because I’ve been using shit like “Still Sleep,” “Don’t Sleep,” so I didn’t know if I wanted to keep it or switch it up.
Have you ever seen the show?
I've definitely seen the show. I seen it on accident.
How is this upcoming album going to differ from Stay Sleep?
They’re always like, “I need something like Still Sleep,” and I’m just like, “Damn, I don’t know.” But this is a lot of growth from that. I feel like I still got the same vibes as the last one, because Still Sleep is fun tracks, pain tracks, and this the same agenda I went for; I wanted to have all types of music on it.
Was there any pressure to make sure this album satisfies fans who loved Still Sleep?
Hell yeah, there’s always pressure because it’s like, once you do good you have to do better every time. That’s my goal: I’ve been trying to do better every time.
One thing they have in common is great production from Great John. Why do you and him work so well together?
Probably because we literally have just sat in a stew for a million nights, even if we're not doing anything. Just listening to beats, falling asleep to beats, waking up and using a beat. He’s more than just a beatmaker; we’re like family. The connection is different.
This is the first time you’re using a self-portrait for the cover art and not something drawn. What made you go in that creative direction, and how does the cover reflect the album?
I don’t even know. It was like a run-and-gun. Because when I listen to the music and I see the picture, it just goes.
What’s the biggest thing you want to prove with this upcoming album, especially considering fans haven't been able to hear from you in a little over a year?
That I can still go up without doing drill.
You were talking on OTR about how you wouldn’t fully categorize this new album as drill, and how you started your career in drill but now feel like you can make whatever records you want. Do you feel like younger artists use drill as a tool to get hot and then abandon it later?
It’s cool right now. I fuck with it, but it’s watered down now. It's not what it used to be. There’s too much of the same shit. Niggas get on a track and they all saying the same shit in different ways. Don’t get me wrong—some of this shit’s fire, but some of it is dirt. I just don’t think it is the same, or the way it used to be.
Lil Tjay said something similar to me. He said that it’s somewhat dying.
Exactly. It’s here because you got the younger generation still paying attention to it. But I feel like [for] the niggas who really know, it's just meh. I get that it’s music, but it got to be real and authentic. It’s like now, niggas is hearing what one person said and be too repetitive. I like when they switch it up and make it different. Figure out your own flow. That’s how I think I started to go up; I would sit in the studio and figure out my flow and perfected my craft. I’m still working on it, but I feel like I found my own lane.
I get it, but it’s like why not just come out the way you want to be? Don't come and make a drill song because that’s what’s lit. I started off with drill music, but not because I wanted to get lit off drill and then switch my shit up. I was rapping about my life, and it just sounded like drill music. It’s the same thing I’m doing now, just about my life.
How did you break away from being pigeonholed to the subgenre?
Just by staying in the studio. Experiences will always help you and going through different things, but staying in the studio and making songs that you don’t like makes you go harder. Because you know you can do better than this.
What was it like putting this album together while dealing with so many other things outside of music?
That shit was hell. There were points when I was in the studio and thought I lost it. I couldn’t make a song for weeks. I was putting shit on a beat and just didn’t like it. It was hard.
What kept you anchored and focused while you were working?
The fans. Sometimes I would go through my messages and see the shit that they say and remind myself that I can’t stop.
What do you think your and Sheff G’s biggest impact on drill and New York rap has been?
I’ve heard a lot of niggas saying we were the reason they started rapping. I don't know their names, but I've seen a couple on On the Radar. The only person I can really remember though is my son Dougie B. He’s seen me and he told me, and I appreciate that because niggas won’t tell you that.
How have Sheff’s spirits been?
He’s sturdy; he’s good. Even when something is wrong, he’ll call you laughing. He’s always in good spirits.
What does success look like to you at this point in your career?
I just want more plaques and more money—that’s it.
Do you still care about the King of New York title?
I feel like you leave that up to the people. You let the people say shit like that.
What’s next for you?
I’m trying to tour. That’s my favorite part of this shit—is doing the shows. I don’t care where it is; I just like being somewhere else other than my hometown. Especially when I got the homies with me, just going somewhere other than where we live at is mad cool.
