Sleepy Hallow and Sheff G established Winners Circle Entertainment as a leading label harnessing the talent in the Brooklyn drill scene. Sheff is the more traditional of the two while Sleepy Hallow’s wide range of influences, from L’A Capone and Kendrick Lamar to classic dancehall records, has turned him into one of the most exciting rappers to come out of the East Coast in recent times. His gruff voice executes pain-riddled melodies with ease, effortlessly switching into rapid-fire triplet flows detailing his surroundings in New York. That’s a commonality he shares with his peers but it’s his ear for beats that sets him apart. His sound is a combination of the sounds of drill in Chicago, and blog era fixtures like Chance The Rapper and Kendrick Lamar. The influence of dancehall is ultimately what informs his appreciation for a good sample, as heard on songs like “Tip Toe” ft. Sheff G or “Deep End Freestyle.”

“For me, it’s always the sample,” he told HNHH on the latest episode of On The Come Up. “Like, the ‘Deep End’ sh*t. Some people say the melody or the sample sounds soothing, but the way that I came on the track, it wasn’t soothing. So, I don’t know how, but that sh*t just blended perfectly.”

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Image provided by the label. Photo credit: Kirby Esquea

The Winner’s Circle rapper is fresh off of the release of the deluxe edition of Still Sleep?laced with an additional 11 songs with appearances from Coi Leray and Skillibeng, Sleepy's pushing his own creative boundaries in an effort to refrain from being repetitive.

The release of the project also comes during Sheff G’s incarceration. Sleepy’s currently holding down the team without his partner-in-rhyme but they communicate frequently to make sure operations are up to speed. 

“It’s a lot, but I got it ‘cause our team is Gucci. I still could speak to Sheff, so if he want to do a certain thing, put something out, he could just let me know. It’s not like I got to put it on my back,” he told us. “Sh*t is heavy, it’s hard, but you can’t quit. You can’t give up. N***as came too far to be stopping. I just got to work.”

Prior to the release of Still Sleep? Deluxe, we caught up with Sleepy Hallow for the latest episode of On The Come Up where he discussed his latest album, Sheff G, and why “The Art Of Peer Pressure” is one of his favorite songs from Kendrick Lamar

WATCH: Sleepy Hallow "On the Come Up" episode

HNHH: Who is Sleepy Hollow?

Sleepy Hallow: Artist from Brooklyn. Going crazy like — he’s different. He don't like to pursue the same things a lot of artists pursue. He tries to come different, in every aspect.

What lane did you create for yourself?

I say that based on the feedback I get. People are like, “Oh, you different,” especially with my latest drops. My favorite thing that people say is, “You don’t sound like nobody.” I’m trying to create my own lane type sh*t. 

What is it about Brooklyn that has a different energy, and what do you love most about Brooklyn?

I don't know. I don’t know if it’s just ‘cause I'm from here, but I just feel like my city is more convenient for me, like everything I grew up with. It could be as simple as your corner store being right on the corner. You could just stop and go right there. I done been to other places where you gotta drive mad far to go to the store. That sh*t be wild. [Laughs] Corner store, bacon-egg-and-cheese. I need that. 

What was it like growing up in your neighborhood? What was the trek like, going to school every day? What would someone see? 

I was living out here. My high school, I went to Queens because my crib had burned down in Brooklyn, so I moved to Queens for like a year. I was going to high school out there. Me going to school out there, I didn’t really f*ck with nobody out there, so I used to have to get on a train, come back to Brooklyn, chill with the homies, then go back to the crib. For a whole year, it was just back and forth. I only went to high school going into the 10th grade. I ain’t go no more.

What was happening when you decided to drop out?

Other people probably wouldn't think the same, but I feel like I had better stuff to do than being at school and sh*t, so I could make a life for myself—in the streets or wherever—just not at school. 

What was the music like for you growing up in Flatbush? Who were the local rappers you were checking out and that you had seen on the block that ended up making it big? 

We used to be in the 9, in the 90s, and that's like East Side. We used to see Rowdy Rebel and them. They really got lit, but other than that, I don’t really think nobody else. That was really it, though.

Were you a good student? 

School-wise, I couldn't really function in a classroom, like writing and sh*t? I could write. I could make some sh*t sound good. Art, I used to like to draw and sh*t. Other than that, that sh*t was -- it was just trouble. The only award I probably won in school is Most Improved, and I don’t think that’s too good, ‘cause that just means you ain’t as bad as you was before. [Laughs] N***, you alright now. [Laughs] You improved. 

"School-wise, I couldn't really function in a classroom, like writing and sh*t? I could write. I could make some sh*t sound good. Art, I used to like to draw and sh*t."

I mean, but that’s progress, right?

Yeah, I had shown some kind of progress, but it was a point I had got left back. Teachers told me, “Yo, you do your thing. Like, middle of the year, we’ll put you in the next grade,” so that used to make n*** like, “Damn, I ain’t tryna be left back. Let me try and straighten up.” But then, it got to the middle of the year, and you not in the next grade. I don’t even think I did good enough to be put in the next grade, so it was just like “Aw, f*ck it.” 

Can you tell me a little bit about art? Do you still draw in your spare time?

Oh yeah, like if I got free time and sh*t, or I’m bored, or mad shit on out my mind, [I’ll] just draw some sh*t. 

Is that ever something you'd pursue further?

Hell yeah, like when I’m some old n***a retired? N***as gonna be buying my own paintings. [Laughs] I gotta learn how to paint, though. I can draw a lil’. I can look at something and draw it, another drawing— I could try. I’m alright, though. I don’t think I’m horrible. At one point, I wanted to just draw and sh*t with people, but that sh*t ain’t work out. 

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Johnny Nunez/WireImage/Getty Images

I wanted to ask you about the music growing up in your house. We talked about the guys on the block, and you said Rowdy, but what were your parents playing in the crib?

Sunday, I just remember you’d just hear… I don’t even know. I really remember my brother playing music. He used to play mad Jamaican music, like everything that was hot. Everything that was lit from our generation. Back then, that’s like Young Money. Young Money was lit for us. Kanye, too. I’m still young, so probably, like Drake was -- I wanna say gettin’ OD but probably like that time. Like, Young Money time, that’s when I was really looking at music. That’s probably when I decided I wanted to do music around that time when all that sh*t was poppin’.

Were you born in Brooklyn? 

Nah, Jamaica. 

At what age did you move to Brooklyn? 

When I was five. I came out here when I was five. I don't really remember too much from Jamaica. I just remember weird sh*t. 

Can you elaborate a little bit about that?

I remember the principal. If you get in trouble in places like that, the principal, they can beat you and sh*t. I just remember him telling me to put my hand out. Me and my cousin, I think. Something like that. I remember that belt— sh*t was thick, wide. Then I remember being in the crib, making these paper boats, and making them run down the side of the crib. That’s the only two things I really remember. 

What was your brother listening to?

I just remember hearing everything. Soon as I hear old tunes now, I’m like, “I remember hearing that back then.” Most songs, I’ll hear it now, and really think, “Yo, I heard this back then.” I wouldn't really know specifically. All the mainstream shit when I was like 12, 13, I was listening to all that— all the mainstream, and then whatever else. A little bit of underground. I could say underground like when Chance the Rapper first came out. I was listening to his sh*t, too. Aside from the drill, gangsta rap and sh*t, I was looking at the other n***as who were artists, making real music and sh*t. I always looked at that sh*t like, “Bro, that sh*t fire.” Nobody specific, but they talking about girls, this, personal sh*t— your life, but it’s still lit. I was like, “Yeah, I want to do that type of sh*t.” Like, my way, obviously. 

When I first came out, it was straight drill. So, it’s like, ‘how this n***a going from this, to making this sh*t.’ But they like this sh*t. The new sh*t I do too, they like it. I’m even getting more— I’d say I got more further with the sh*t I do now than doing the drill. The fact that this is something I been wanting to do, make real artist music, I f*ck with it. I’ll always do drill, of course. 

Are you seeing your fan base expand beyond your usual audience? 

It’s definitely more global. Even my old fans, they’re like, “Yo, the new sh*t fire.” They’ll probably say they want some drill, but they’ll never discredit the new shit. They'll probably say, ‘add a drill song,’ but they'll never discredit the new sh*t. 

I read the artists that influenced you the most are Biggie, J. Cole, 50 Cent, and Kendrick.

Hmm… Yeah, I can live with that. 

Biggie makes sense to me ‘cause you’re from Brooklyn.

Kendrick? Everybody when I tell ‘em that, they look at me weird. For me, I don’t know. A lot of his sh*t just stuck with me. I could relate, especially when he came with that whole m.A.A.d City sh*t. That was my sh*t. Not even gonna front. It’s more me relating to sh*t. 

"Kendrick? Everybody when I tell ‘em that, they look at me weird. For me, I don’t know. A lot of his sh*t just stuck with me. I could relate, especially when he came with that whole m.A.A.d City sh*t. That was my sh*t. Not even gonna front. It’s more me relating to sh*t."

What's your favorite song off the album and why?

Oh man… was it even on the album? I think “Peer Pressure” or something like that?

The Art of Peer Pressure?

Yeah. Was that on m.A.A.d City? Yeah. That sh*t, n*** don’t talk about but that sh*t is real. I’ll say more on the street, that sh*t is really peer pressure. That sh*t is there. Some people be going through that sh*t and don’t even know. They be thinking they acting a certain way— that’s not true. That don’t even be them. It be their crowd. That sh*t stuck with me OD. That made me think, “Damn, I’m on this?”

Did that song make you a little bit more aware of those type of situations?

By the time I really -- I understood all that shit. I wasn’t even gonna let myself get in that situation, so before I even do something, I’m gonna talk to myself. I already know what could happen, I know what can’t happen, so if I don’t wanna do it, I’m not even gonna do it. Defeat the possible peer pressure that could even come with that. 

Talk to me about the J Cole influence.

That was another thing. That's me steering away from the gangster sh*t. When J. Cole probably dropped, [“Work Out”], I probably even -- when I started rapping, I used to just listen to mad songs and try to write remixes. I probably did that sh*t ‘cause that sh*t was different to me. He talking ‘bout some sh*t. That ain’t even on drill, drill, but it still fire to me. So, that’s wavy. Drill will forever be here but I like doing that other shit. 

"When J. Cole probably dropped, [“Work Out”], I probably even -- when I started rapping, I used to just listen to mad songs and try to write remixes. I probably did that sh*t ‘cause that sh*t was different to me. He talking ‘bout some sh*t. That ain’t even on drill, drill, but it still fire to me. So, that’s wavy. Drill will forever be here but I like doing that other shit."

Just on the drill side, who was influencing you on that?

That was my life. I was just talking about my life. We used to listen to drill rappers, too, though. Of course— especially Chief Keef, L’A Capone, all them. That sh*t was traditional for us. This is where we come from, why not? 

It’s like they’re over here, Chicago, wherever. They talkin’ the same sh*t we talkin’ about. It’s like we’re living the same lives. We’re in two different places going through the same sh*t, so of course, some of the same stuff is going to be said ‘cause some of the same stuff is happening. It’s just all about how you present that sh*t in the music, in the drill. 

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Johnny Nunez/WireImage/Getty Images

Did you ever have a first job and what was it?

Nah. Never. My mom—I was probably 14— she tried to get me in Summer Youth. Mad people in there. I’m sitting in there. I sat there for like 10 minutes. I’m like, “Nah, I’m out.” I just dipped, went to the crib. That’s when I was living in Queens, too. So, I got on a train, went to Brooklyn. F*ck that. Tried, though, but never. 

The closest thing to a job... I think it was summertime. One of my teachers used to tell me to pull up, help him. He used to give me bread for that sh*t. That was probably my closest thing to a job. He wasn’t really a teacher, teacher. He was just in the school and sh*t. He was mad cool, though. I was like, “Bet.” That’s the only thing though. That’s the closest thing to a job.

Talk to me about your ear for beats, especially on the new project. It feels like you're experimenting a little bit more.

That sh*t be different. But in the beginning, we used to go on Youtube, take a beat, and just rap. The beat is already structured, you can't edit the beat, you can probably do drops and sh*t. But now, we got our own producer, so we could talk and say, “Yo, you know this sound? Make this sound go like this,” or whatever. You’re kind of co-producing the beats, too. For me, it’s always the sample. The sample was always fire to me from when I was young. I used to hear that shit. I ain’t know what they called it, but I used to hear something like, “Yo, that sh*t fire.” I’m a rapper now, so I started doing it in my own ways. Like the “Deep End” sh*t. Some people say the melody or the sample sounds soothing, but the way that I came on the track, it wasn’t soothing. So, I don’t know how, but that sh*t just blended perfectly.

Even the way you were describing listening to old Dancehall or reggae tracks, do you think that influence from back then seeps in when you're picking out beats and samples?

I’m definitely seeing that, too. I feel like everything I heard, all of the music I heard -- I was just a music machine. I don’t hear it in my head, but I feel like it’s somewhere in there. The beats, all that sh*t is just in there, lingering. Maybe, little pieces of it but all them little pieces just connect and do what it do. 

Are you considering your approach to the track when you're thinking of the sample in your head?

Nah. Honestly, nah. My thought be like, “I don't want to sound how I sound on my last song.” Or let’s say I did “Deep End Freestyle,” I use the melody, drums, whatever. If I’m trying to do the same thing and trying to do the freestyle, I’m usin’ the melody and drums, I have to be like ‘I cannot sound the same.’ The whole flow just gotta be different. That’s one thing fans hate too: they don’t want to keep hearing the same flow. [I’m trying to master] switching up the flow every song and having it sound good— because you can switch up the flow and that sh*t be ass.

We’ve all watched your evolution sonically over the past three years. In terms of expanding your sound and on the topic of Still Sleep? Deluxe, was that a concerted effort to expand your sound from the start of your career? 

To be honest, my plan was to go crazy every time, but obviously, it ain’t gon’ be that every time. That’s just the plan: go crazy and come different, every time. Every album, every song should be better than the last song I recorded. If it’s not like that, I’m not gonna like it. I’m not even gonna use that sh*t. If I feel like I’m backtracking, or if I do a fire song, then we come in the booth, two weeks later, a month later, it don’t matter. I’ll make a song, and I’m still stuck on the last song I made. I don’t really wanna use that because it can’t compete with the other song. But sometimes, it’s debatin’ ‘cause it’s like if I make a drill track, and then I make some smooth sh*t, then I’ll just drop both because it’s two different genres and sh*t. 

Break down the deluxe to me a little more. 

Like I just said, it got a lot of switched flow, it got all of that. For the fans, it’s a couple of songs that I previewed and saw that they really want, so I made sure I put those two songs on there. Probably like 8, 9 new songs — a couple of remixes. 

We already know “2055” got a remix. “2 Sauce” got a remix. You know “Mi No Sabe” got a remix. That might be it.

Talk to me about the Coi Leray remix. Out of everybody in the world, why Coi Leray?

When her sh*t first dropped, that went crazy. I was f*cking with it. I put a couple of my mans onto that sh*t, people around me. That sh*t, it was alright. I f*ck with that sh*t. When the remix came out, I ain’t really know who to use. She came up in the conversation, I’m like, “Yeah.” I heard it, I’m like, “Yeah, fire.” I felt like she would’ve walked on that sh*t. That’s really how it happened.

After doing the drill stuff and then seeing the success that this different take on drill, what’s your reaction to that? 

When you first tryna switch it up, you get this feeling like, “Yo, it’s possible that when I drop this sh*t, n*** gon’ be like, ‘What the f*ck is this n** doing?’, Like what are you talking about? Where is the other sh*t at?” But I dropped it, and it was just like, 'Yo. He’s going crazy.' Once you’re thinking about something so much, you’re thinking about happening in a certain way so much, and when you do it, it’s the whole opposite like, Yo, what the f*ck was I thinking? I had to be bugging. That sh*t just pushes you more. If you’re in your shell, [and] you don’t know how to really transition, that’ll motivate you to transition even more. So I did it, and it went crazy— n***as was f*cking with it, so why not? You don’t know what that sh*t could bring. Open up more doors, all that. 

Do the numbers matter to you?

I mean, yeah, ‘cause that’s the more people that are tuned into you. That’s the more people that see you. That’s new fans. Who doesn’t want new fans? Any rapper wants the whole world to be fans if they had a way to make the whole world fans of them. The numbers do matter. That’s what counts, that’s what makes the money. That’s everything.

It felt like on your first two projects, you were keeping a lot of the collaborations within your circle, but nowadays it seems like you're expanding outwards, even on the deluxe. 

That’s because I really wanted to apply pressure on my own before I really start doing features with people. Where I’m from -- with the handouts and shit -- n***as will be like, “Yo, I did this. I made this for you personally. I did this for you.” N***as ain’t trying to hear none of that. So I would rather do sh*t by myself. Then, when I get to a certain point where people are f*cking with me just off the rip, like, ‘Yo, son nice. He did that,’ they’re gonna f*ck with me. My management really pushed me and sh*t to do features and all that sh*t. I don’t really meet people. I don’t really like people like that. I only like organic sh*t, though. That shit be a hassle with features and sh*t. I like everything organic. I don’t really like all the extra shit.

You don't really seem like the type that's playing the industry game, so to speak. 

Yeah. Whatever the industry game is, I don’t want no part. I done seen a lot of weird sh*t, too. We be tryna stay away. Stay with the circle.

How did "Panic" turn into a series?

After the first one, we just called it “Panic” because n***as was panicking -- not us, but n** was panicking. So we just said, “Yo, Panic.” After we did another one, we did another song, we just had a little back and forth on it, so that would be me and Sheff, doing the back-and-forth, that was like a panic. Anytime that would happen in a song, I would always want to be like, “Yo, this could be like ‘Panic’.” But we made that decision together, to put that sh*t. After that, if we bug out on a track— a drill track— we bug out, it’s just like, “Nah. You’re going too crazy. It’s panic.” It’s just panic. If it was a song where there was a hook, verse, hook, verse, then it was just a regular song, but anything back to back, we made it Panic record.

How would you describe the evolution of Brooklyn drill from the early days of you starting off with UK drill beats to the sound you’ve developed recently?

You don’t really do it the same. This sh*t’s different. We’re making the beat to ourselves now, so we have the ability to structure the whole track the way we want it. Before the beat was already made, you don’t know it but it limits you from saying certain stuff ‘cause the beat is already made, so you just got to rap to fit the beat. Us making the beat ourselves is what made us more open to saying different stuff ‘cause you’re making the beat with bro. All I do is tell bro, “Yo, whatever it is. I don’t know what it’s called, but you could do this right here?” I structured it myself. I feel like we made the record way better that way. too.

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Eli Fross, Sheff G, and Sleepy Hallow attend the Sheff G "The Unluccy Luccy Kid" release party - Johnny Nunez/WireImage/Getty Images

How’s Sheff been these days? [Ed. note: this interview was conducted prior to Sheff G's sentencing]

 

He good. Free Sheff, too. He good, though. He chillin’

Have you talked to him recently?

I talk to him everyday. Almost everyday. 

Is there anything that he would want you to tell the fans on his behalf? 

Free him. Me and bro, we love the support. When this sh*t started, sometimes, we would go through comments and sh*t, and that’s what kept us rapping— the good comments. We’re like, “We got to keep going, bro.” ‘Cause of them. ‘Cause of y’all, the fans. So, y’all got to keep supporting my boy. He gon’ be steady dropping heat, too, so it ain’t like he too far. 

"Free [Sheff G]. Me and bro, we love the support. When this sh*t started, sometimes, we would go through comments and sh*t, and that’s what kept us rapping— the good comments. We’re like, “We got to keep going, bro.” ‘Cause of them. ‘Cause of y’all, the fans."

How have the past few months felt for you having to hustle and keep the name alive on your own?

It’s a lot, but I got it ‘cause our team is Gucci. I still could speak to Sheff, so if he want to do a certain thing, put something out, he could just let me know. It’s not like I got to put it on my back. I still got a few sources that are gonna get me right. 

Sh*t is heavy, it’s hard, but you can’t quit. You can’t give up. N***as came too far to be stopping. I just got to work. 

I'm not sure if you've ever responded to this, but there was an interview where Sheff explained that the first time you guys met he was with a crew of people who were going to confront you. He said that you practically stared them down and from there, you guys were cool. Can you share your perspective on that day?

In the beginning, we did have problems. I was on my own, I was really by myself. I wasn't really a part of that, so if I had a problem with them, they was like, “Yo…” Like, they seen that I was on timing. And when we finally met, it was just cool from there. We was on the same time, been through the same shit, going through the same sh*t, so we were Gucci. And we knew some of the same people, so they were just like, “Yo, there’s no point in that sh*t. Y’all n***as, just be cool.” We were just like, F*ck it. We’re cool. We’re brothers.

Final question, what do you got going on? What can fans expect from you after the deluxe drops?

Heat. New heat. I’mma be experimenting a lot, so expect the flow to be crazy. All types of sh*t. A couple features, probably. And I’m going on tour— probably the end of October. 29 cities, the Still Sleep? tour. It’s lit.