‘It’s Way More Than Drill’: Inside Sheff G and Sleepy Hallow’s Winners Circle

Sheff G and Sleepy Hallow, two of the brightest talents of Brooklyn's drill scene, have teamed up with RCA Records for their Winners Circle crew.

Sheff G and Sleepy Hallow

Image via Winners Circle

Sheff G and Sleepy Hallow

In 2019, Brooklyn drill was the sound that was set to take over the world. The style, a hybrid of U.K.-style beats and Brooklyn street talk, first gained widespread notice in 2017 with a pair of songs: 22Gz’s “Suburban” and Sheff G’s powerful reply, “No Suburban.” Those tracks were key to introducing a young English producer to the world: AXL Beats, who helmed both songs and went on from there to bring his signature sound to an array of artists (including Pop Smoke and Drake). 

In 2020, Sheff G has moved far beyond “No Suburban.” The Flatbush rapper has expanded his musical reach beyond drill, and now he’s preparing to grow his industry reach as well. Sheff G’s label and crew Winners Circle—Sheff, rappers Sleepy Hallow and Eli Fross, producer Great John, and management team Jeremy “Jerm” Soto and Karel “White” Jorge—have teamed up with RCA Records. The name, they tell Complex, came to them while watching SportsCenter (Soto explains, “I think they were featuring the horse races, and someone said, ‘Off to the winner's circle.’ We thought it made sense.”)

“We just felt like RCA was the best place for us,” Soto notes. He points out the fact that RCA didn’t have “that many urban acts in-house” was an advantage, because the Winners Circle crew wouldn’t have to compete for time, attention, or resources. “And we felt like they saw our vision the clearest,” he continues. “It was a perfect fit for us.”

But, everyone involved emphasizes, don’t think of Winners Circle as a drill label. “We are artists,” Fross emphasizes. “Winners Circle is well beyond the drill sound,” agrees Soto.

“A lot of the content is still drill, because they've all lived rough lives as young men,” Soto continues. “But if you listen to the backdrop that they create with Great John, it’s new sounds outside of drill. They’re creating their own sound right now.”

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The opening salvo in the Winners Circle/RCA partnership was the video for Sheff and Sleepy’s “Tip Toe,” which takes Tiny Tim’s novelty version of “Tiptoe Through the Tulips” and gives it an Insidious-inspired horror movie twist.  The impetus for the spooky sample came from Sleepy.

“He just walked in with this crazy idea,” Soto remembers. “We’re all looking at him funny—like, ‘What is this?’ He's like, ‘No, watch.’ John made the beat real quick. Then [Sleepy] went in there and freestyled off the top of his head, and history was made.”

Quick-working Great John provides the sonic backdrop for Winners Circle.

“All of our artists got to work with John,” Sleepy Hallow explains. “Even the future ones.”

The crew is coy when describing exactly what makes the producer’s work stand out—they don’t want to give away the “recipe,” Soto explains. But it’s more than just the beats. Great John records and engineers all the crew’s music as well. He’s the key element to making it “drill, but not drill,” as Soto describes the sound.

And the key element to this new partnership with RCA, according to the Winner’s Circle crew, is the people involved. They admit that they haven’t gotten any good DJ Clue-era stories from RCA A&R Skane Dolla, but he has given the crew guidance throughout the process. And they can rely on music biz lifers like label CEO Peter Edge and RCA president Mark Pitts. 

“They’ve all been around and been part of history,” Soto says. “And they’ve all created their own history. Now they’re trying to help us carve our own little piece of history as well.”

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The newest piece of history they’re hoping to carve out is for Eli Fross. Winners Circle has big plans for him—most immediately, several videos leading up to the release of a project, to be titled Caesar. Interestingly, the record is not named after the Roman emperor. Instead, it’s titled after the leader in the Planet of the Apes franchise.

“Caesar, he was different from every other gorilla,” Fross explains. “He could speak English a little bit. When you see gorillas, you see them as a pack. Everybody looks at them like violent creatures. So basically, I was showing how a hood dude growing up out the slums could change.”

Fross, a self-described “GOAT,” has big plans and outsized confidence in his talent. He insists his artistry extends beyond rapping. And his Winners Circle crew seconds the notion. Collectively, they view themselves not just as a business entity, but as family. Their goal, they say, is to continue breaking ground.

For Sheff, that means continuing to go far beyond “No Suburban.” Looking back on the past few years, he locates his 2018 duet with Sleepy Hallow called “Flows” as a key turning point. The song, about “elevating your life,” was a change for the pair. “We don’t usually make songs like that,” Sleepy admitted to Genius.

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“‘Flows’ was one of the songs that showed everybody that we could step out of just being drill artists,” Sheff explains. The successful experimentation of “Flows,” he says, led to other successes like the sequel “Flows, Pt. 2”; and a pair of tunes by Sleepy with Sheff on the assist, “Breaking Bad” and “Molly.”

And now, with Winners Circle having RCA (“a perfect fit,” Soto says) on its side, the tight-knit crew believes that anything is possible. They plan to sign artists, keep growing the ones already on board, and in general expand beyond the scene that originally brought them to prominence. 

“It’s way more than drill,” Sleepy emphasizes. 

Soto agrees. 

“Sheff and Sleepy and Eli, they’ve flirted with new sounds outside of drill. They’re creating their own sound. I think that’s what's best about what they’re doing.”

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