Despite Legal Setbacks, Sheff G and Sleepy Hallow Are Still Smiling

Sheff G and Sleepy Hallow are constantly looking on the bright side, even when their current circumstances may seem bleak.

In late March, the two New York drill rap pioneers visited the Complex office for a rare joint interview. Just two days later, Sheff G pleaded guilty to attempted murder and conspiracy charges, resulting in a five-year prison sentence.

However, despite his impending fate—and presumably knowing what was to come in the days ahead—Sheff’s energy remained jovial. He was still smiling and optimistic about the future as we talked. He spoke passionately about cooking up a long-awaited collab tape with Sleepy and about the possibility of having another child in the future.

The two were also full of banter, which makes a lot of sense considering they’ve been best friends since middle school. The irony, however, is that their introduction came because they were supposed to fight each other. "That's why you can't listen to other people. You’ve got to see what's going on for yourself, because we came to jump him," Sheff G tells Complex, laughing. "We got mad cool after that," Sleepy Hallow adds. "I ended up fighting somebody else on a different occasion, and then when I met him, we were already cool."

Now, they have directly impacted the current decade of New York rap. Sheff G helped pioneer the original Brooklyn drill sound, creating street classics like One and Only, while Sleepy Hallow effectively reinvented the scene and laid the blueprint for its current, sample-heavy version. This shift was driven in part by producer Great John and Sleepy’s album Still Sleep. The two projects are approaching their five-year anniversaries, and when reflecting on the impact of their music, both Sleepy and Sheff agree that it showcased the depth of their artistry."

“[Still Sleep and One and Only] showed people our growth in the music world period,” Sheff said. “Aside from just the drill music because of all the melodic sound and shit that we put together.”

Sheff G's current legal situation underscores the disruptive impact legal troubles have had on both rappers' careers. After a breakout year in 2020, Sheff G was sentenced to two years in prison on gun possession charges. Meanwhile, as Sleepy Hallow was solidifying his place in the melodic drill wave with tracks like "Deep End," he faced a series of legal issues, including multiple stints in prison between 2022 and 2023. In May 2023, both he and Sheff G were indicted on gang conspiracy charges.

Legal troubles have been such a significant part of their narrative that last summer—when the two made national news after appearing at a Donald Trump rally in the Bronx—some assumed it was a craven attempt to eventually secure a pardon. (Both Lil Wayne and Kodak Black received pardons from Trump after publicly appearing with him.) However, according to the rappers, the meetup was a spur-of-the-moment decision. They also seemed unfazed by some of the criticism they received, saying, “Everyone is entitled to their own opinion,” in reference to the backlash.

Outside of music and politics, Sleepy Hallow is venturing into a new digital frontier by debuting new music with a Fortnite performance in the game. “We’ve got a collab in the works, and I’ll be doing an in-game concert with gameplay and everything. I’m going to stream that too," Sleepy said. "I’ll perform ‘Anxiety,’ ‘2055,’ and some unreleased tracks.”

We caught up with Sheff G and Sleepy Hallow to discuss defining a generation of New York rap, their appearance at a Trump rally in the Bronx last year, the making of "Anxiety"—which is having a moment again thanks to Doechii—and more.

This interview has been edited and condensed for clarity.

Is it true that you two met because you were supposed to fight each other?

Sheff G: That’s a fact.

Sleepy Hallow: Even when we got close, it was through mutual friends. So us not liking each other was also through mutual friends. But once we finally met, it was just like, “Nigga we mad cool.”

SG: That's why you can't listen to other people. You got to see what's going on for yourself, because we came to jump him.

SH:  But it just wasn't that. We got mad cool after that. I ended up fighting somebody else on a different occasion, and then when I met him, we were already cool. This was in middle school..

How would you both describe the energy of New York rap right now?

SH: I feel like New York always had eyes on it. Even when we wasn't rapping. It was always eyes on New York just because the name alone, and what they expect of people coming from New York.

SG: But I feel like it’s at a good point right now, because all the artists, everybody fuck with each other heavy. Niggas be in spots together, the clubs together, everybody going crazy. There's no funny vibes. Everybody pulling up. You know how usually niggas be scared to come to each other's sections. Everybody will act like they're the biggest, there's none of that. Everybody pulling up on each other.

SH: Besides the little side shit that be going on, you know how drill rap get, but facts. Everybody be chilling, linked up. I feel like everybody is [now] noticing that getting money and getting away is the goal. Crashing out is not the goal.

I feel like a lot of that has to do with growing up too.

SG: It's the belief, though. I could tell you right now, “Yo, I'm making a million dollars.” But unless you actually see somebody doing it or see the process of doing it, you're never going to fully believe it. It's just going to always be a story in the end. So now that everybody can see each other really doing it, I was like, “Bet, it's possible.” It's really something I could achieve. So now everybody's relaxing and really focusing up on their goals. Like, “Damn, I really could move my mom out the hood. This nigga Sleepy did it. Sheff did it, and they came from nothing.” So now they know for a fact, it's really a way you could do it. If we did it, everybody can do that shit.

Sleepy, next year will also be the five-year anniversary of what I think is one of the most important New York rap albums of this decade, Still Sleep. What do you think is the legacy of that project?

SH: That's when I started to find my sound. That's when we started making music and knowing our ability in the music world for real. That's when we really started saying that with [Great] John and shit. 

SG: [Still Sleep and One and Only] showed people our growth in the music world period. Aside from just the drill music because of all the melodic sound and shit that we put together. 

SH: Yeah, that's when we started to try and mix the 808s with the melodic sounds and shit. 

What do you remember about working on those projects during COVID times?

SH: That's what fake made it hard because that shit started going up and you couldn't even go outside. [But] we treated that shit like it was regular. We was bringing the function to us. Everybody who wasn't scared to come outside? Bet, link up we outside. Maybe being inside helped because it made people listen to everything.

How did “Anxiety” come together? How did you find the Doechii sample?

SH: I was scrolling. I seen her freestyle it first and then my man sent it to me and I was like bro, I was just listening to this shit. I listened to the whole freestyle. I'm like, “Yo, this shit is so fire.” I couldn't take the whole freestyle, so I took the hook. I already had a song called anxiety because I love speaking about that topic. I sent it to John, he did the beat, and we just went crazy. Shoutout to Doechii.

What do you think of the state of drill in 2025?

SG: I feel like the fact that you still mentioning it, means it's still here, but you know it’s about how you feel. I keep telling people that drill is not a particular sound. It's how the music makes you feel. Why you think we have sexy drill now and all that. It's about if it make your adrenaline rush.

SH: The beats too. The beats and the instruments that's being used. I feel like people often hear a certain instrument, and know that's drill. So it's like it drill made its own name and own sound and shit. 

SG: I don't think drill will ever go away. Especially people that like to work out in the gym. Those be the main people [who listen to it]. You don't got to use what I'm saying and try to go do that. Just use it to your own way, because when you go to a show and you see the crowd, the crowd is college students. It's a different type of crowd. They take your words and they use it how they use it.

Did y’all ever think that drill could take it this far?

SH: No, not really. Especially when there's people saying you got to change your sound. They were all wrong. People are going to love you for whatever you doing. 

When is the Sheff G and Sleepy Hallow joint tape coming?

SH: We’ve been working on that every day. It's going to be us together. I know that shit is highly anticipated so we got to make it exactly what they been asking for. 

Walk me through how you ended up at that Trump rally in the Bronx last summer?

SH: I don’t know, bro. I got a text, a call, and I just went, “Bro. People think we actually speak?” We didn't even speak for real. [Sheff] was just like, “Yo, come on stage.” I'm like, “What? Come on stage and do what?” I heard [Trump] say my name and I was like, “No way this is about to happen.” Coming from where I’m  coming from, it's like me with the president? 

SG: Tell him the truth, man. Listen, Secret Service picked us up. They like, “Yo, we need y'all man.” Brought us to spot, y'all see what's going on. CNN, everybody sees the vibes, it's quiet. We world wide now.

Were either of you surprised with the reaction that moment got?

SH: Nah, it was just funny because there are people who dead hate us because we did that. 

SG: I respect everybody’s thoughts. Everybody entitled to your own thoughts. That's going down in history regardless. We were with the President.

What’s next for y’all?

SH: We just trying to get all of this music out, and do it the right way. Ain’t trying to be held up by nobody.

SG: And other than the music, I want to have another kid. Shoutout to my daughter.