Back in June, the 21-year-old released Still Sleep?, his third album and first under the RCA partnership. With songs like “Basketball Dreams (Intro), “Scrub,” and “Tip Toe” featuring his right hand Sheff G, combining drill beats with softer melodies through sampling has become his forte. This knack even led to TikTok virality after he flipped Fousheé’s “Deep End” for his “Deep End Freestyle,” which earned him his first Billboard Hot 100 hit and is the first track on 2020’s Sleepy for President.
“That’s something I been wanted to try since I was young and I first started writing,” Sleepy says. “Samples just sounded fire to me, especially the old ones. Like when you take an old song and give it a new [sound], like how they structure the beats now.”
Billboard spoke with September’s R&B/Hip-Hop Rookie of the Month about his childhood in Brooklyn, partnering with RCA, his friendship with Sheff G and how his hit “2055” is a song for his generation.
Tell me about your upbringing in Brooklyn.
It was lit! I used to want to play basketball, but it just didn’t work out. I dropped out in ninth grade and it was just music after that.
Do you still live there?
Nah, not no more. I live in New Jersey [now].
How did you get your stage name?
That was just my nickname regularly. Where I’m from, if you want to be a rapper, you just gonna keep the same name as your street name. Probably add something else to it a little bit.
So “Sleepy Hallow” was always your street name?
Yeah, that was my street name and I made it my rap name too.
How does your friendship with Sheff G affect your creative process?
We come from the same thing, the same situation, we did a lot together. So us rapping together, we not rapping about false things. It’s easy to relate and work with each other.
Do y'all bounce ideas off each other, record together a lot, etc?
Yeah. Or I’ll have an idea and it’ll be the same or similar to his.
Do you two get compared to each other often? If so, how do you feel about that?
I don’t really care, we both good. You can compare all you want. But some people don’t even know [our voices]. Some people be thinking his songs is mine and my songs is his.
I know in other interviews you two have mentioned a possible collab tape? What's the status of that?
We still working on it, but unfortunately Sheff ain’t here right now so I don’t know.
Winners Circle joined forces with RCA last year. What was the transition like going from independent to signing with a bigger label?
I still see everything the same. I still gotta put in that same work.
Your creative freedom stayed the same also?
Why do you think “2055” is a fan-favorite?
I feel like everybody can relate to it. The song is based on the future. But it’s you stepping out of your regular life, everything you dealing with and you just chillin’. Don’t gotta deal with your problems, it’s just lit. I feel like a lot, especially my generation, they going through a lot. They can really relate to it.
How'd you get Coi Leray on the remix?
I did it through my label. I felt like it could use a remix with a bigger artist. I don’t really know why I went female, but I f--k with it. It’s fire.
I was surprised to hear you sampled Pink Sweat$ on “Basketball Dreams (Intro).”
Yeah, that’s actually my second sample [of him]. My first album, [on] “Bestie” I sampled him too.
Are you a big R&B fan?
I ain’t gonna front, lowkey I am. I f--k with them lil jams -- but like, I wouldn’t say I could name you a whole bunch of R&B records. At one point I was going to make… like, you see how some of my beats [have] hard drums but the melodies be soft?
Yeah, I noticed that.
Right. It’s like R&B melodies and s--t, but the drums is hip-hop. Drill-type drums.
What's next for you?
I’m working on a deluxe right now, then a new album. I’m about to go on tour soon. Let ‘em know I’m headlining!