Sleepy Hallow doesn’t shy away from illustrating the uglier sides of life in his music. He knows his fans feel empowered by seeing other people go through the same struggles as them, and he’s motivated by their responses to his songs.

“In my comments, people tell me how much I helped them through shit, and I’m always so surprised because I’m dealing with my own shit, too,” the Brooklyn-by-way-of-Jamaica rapper explains. “But there will be certain things I say where people will say it was a motivation for them. That is always motivation for me to open up more and let them know that I’m going through shit, too. Everybody’s got something going on.”

Sleepy first emerged in the New York City rap scene while working with his close friend and Winner’s Circle labelmate Sheff G. Both Brooklyn rappers took charge as leaders of the drill movement, but chiseled their own lane with a fresh approach to the sound. Sleepy turned heads with his popular mixtape Don’t Sleep in 2019, before dropping his debut studio album Still Sleep? in 2021, and establishing himself as one of the first New York drill artists to go viral by utilizing samples in his songs. 

Sample drill has become a popular sound in boroughs like the Bronx, but Sleepy Hallow’s songs like “Deep End Freestyle,” “2055,” and “Basketball Dreams” were making waves on TikTok before most of the current sample drill artists found mainstream appeal. Sleepy is quick to point out he puts his own spin on the sound: While most artists sample classic R&B songs to leverage a sense of nostalgia, he prefers obscure tracks that he finds randomly. And he harmonizes with the sample in a uniquely syrupy way, floating over melodic beats from go-to producer Great John. 

His latest single “Die Young” borrows from alternative artist 347aidan’s track “Memories!” which Sleepy came across while casually scrolling through social media. Then they connected through their management, and “Die Young” was born. “I don’t wanna die young, so I stay with a stick,” Sleepy raps, interloping the hook of “Memories!” that caught his attention in the first place. The song will arrive on his forthcoming project, which Sleepy says will incorporate vibes that appeal to the different demographics of his fanbase.

Not everything has been easy during Sleepy’s rise to success, though. Shortly after the release of Still Sleep?, Sheff G was sent to prison for two years after pleading guilty to criminal possession of a firearm. This left Sleepy without his right-hand man, but he says he had been learning to be self-sufficient as an artist in the years prior. “We always used to go [to the studio] together, so [Sheff] was growing as an artist and I was growing as an artist,” Sleepy says, explaining what it was like growing under Winner’s Circle. “Basically, we learned to be able to stand on our own as individual artists.”

Currently, Sleepy faces legal issues of his own. While details remain unclear, his Instagram page has hinted that he’s currently in jail by posting messages like “free me” in recent days. When reached for comment, his label provided the following statement to Complex: “Sleepy Hallow is currently incarcerated. Sleepy and the Winners Circle Entertainment team appreciate the support they have received from collaborators and fans during this time.”

In mid-June, we spoke with Sleepy about being an originator of the sample drill wave, a status update on Sheff G, and what fans can expect from his upcoming album.