Show & Prove: Sleepy Hallow
Words: Kemet High
Editor’s Note: This story originally appeared in the Spring 2022 issue of XXL Magazine, on stands now.

There’s a war on drill music going on. New York City’s new mayor Eric Adams publicly wagged his finger at the hip-hop subgenre, DJs have cut the violent records from their sets and NYPD’s hip-hop police—a task force dedicated to dealing with rappers—has been working overtime to fight what they think are potential dangers related to the music. But, one of the subgenres most notable flag-bearers, Brooklyn’s Sleepy Hallow isn’t tripping: “I ain’t worried. I make all types of music."

Over the last few years, mainstream rappers like Kanye West, Drake, Nicki Minaj and Migos have all hopped on the wave. “That’s how you know it’s lit,” Sleepy Hallow says. Yet the MC has surfed on a wave of his own. He’s expanded in the genre with a melody-driven approach that pairs nicely with his husky tone and usual lyrics about hitting more stains than a jug of Tide laundry detergent. The result has been songs like “Deep End Freestyle,” “Molly” and “2055,” which combined, have over 600 million Spotify streams, among a myriad others that have added weight to his name.

Sleepy Hallow, born Tegan Joshua Anthony Chambers, came up as the son of two Jamaican parents in the Caribbean town of Mandeville. At the age of 5, Sleepy’s mother moved him, his sisters and his brother 1,600 miles to the gully neighborhood of East Flatbush in Brooklyn for “a better life.” Outside of playing basketball and football, a young Sleepy used hip-hop to escape his street surroundings. “It was really certain beats I heard that were just like, Nah, that’s fire,” he says. “[I would] put headphones on and go somewhere else-type shit.” He salutes rappers like Drake and Kendrick Lamar, plus R&B switch-hitters T-Pain and Chris Brown for having an impact on him.

At 14, Sleepy started putting his own pen to the pad and decided to try his hand at rapping.
“I ain’t even used to rap to nobody, nothing,” he tells. “I used to write my shit and rap to myself.” Sleepy recorded his first track, “Nightmare,” at age 17 in a childhood friend’s living room studio with Sheff G—a rival-turned-friend and now frequent collaborator. Sleepy then uploaded his debut record to SoundCloud.

The ghostly track was equipped with bars about sending bullets through the bubble coats of his enemies. “Ruger waist-deep, run up on ’em, we gon’ send heat/Call it Elm Street, no Freddy Krueger, but you can’t sleep,” Sleepy spat over a staticky drill beat.

With a positive response online, Sleepy’s recordings started to hit different after that track and the aspiring hip-hop star saw money signs. He chin-checked his shyness, formally adopted the name Sleepy Hallow—the title he went by in the streets—and started hitting the studio regularly with the bros. “You can’t be scared to rap, nigga, if you wanna be a rapper,” he told himself.

Tracks like 2017’s “Panic” with Sheff G and Double G were released and began heating up in the Big Apple, putting Sleepy in the mix of Brooklyn’s then-brewing drill scene. But in 2018, Sheff and Sleepy caught fire with “Flows,” a track accurately named for the wavy flair they brought forth in an otherwise rigid subgenre. “Niggas would say that our shit was different from everybody else’s shit,” Sleepy recounts. “That was motivation.”

Sleepy and Sheff’s friends and soon-to-be business partners, Jeremy “Jerm” Soto and Karel “White” Jorge took note of that and introduced them to New Jersey-bred producer Great John in 2018. John ran point on crafting an unprecedented sound that separated the artists from the rest of the drill scene. “Dudes came in the studio and I’m like, These niggas is rough, boy,” Great John says. “You could just see their aura. Sleepy was really quiet. Sheff was always wildin’.”

The trio eventually cracked the formula and laid down the piano-ruling “Automatic,” sparking a long, fruitful relationship that would change their lives. “The sound wasn’t as intricate as the other drill that I was hearing,” Great John adds about finding their sauce. “But it created enough space for the vocal and it would still bang. Then we just took it from there and started going different places with the sound.”

In 2019, a 19-year-old Sleepy unloaded his debut “come-up tape” Still Sleep?, produced entirely by Great John. That same year, Sleepy, Sheff, Jerm and White founded record label Winners Circle, also home to now rising rhymer Eli Fross. “We just wanted our own label,” Sleepy explains. “We figured that was the best way to go about it.” They partnered with RCA Records the following year after Winners Circle’s former Empire distribution deal.

Now with the backing of a major label, Sleepy’s music continues to stick like cold grits. 2020’s Sleepy Hallow Presents: Sleepy For President housed “Deep End Freestyle” featuring Fousheé, a platinum-selling record with the same eeriness of his song “Tip Toe.” “Deep End Freestyle” now has upwards of 200 million Spotify streams. The project also includes “Molly,” a track Sleepy maintains is his best collab with Sheff.

Sleepy’s debut album, Still Sleep?, came out in 2021 and was led by the introspective “2055.” The platinum track, with Coi Leray on the official remix, has gained over 300 million spins on Spotify. “That shit takes you somewhere else,” Sleepy says. “I had a feeling it was going to be what it was.”

Now in his best form, Sleepy is cooking up his sophomore album, slated for release this fall. “New flows, new vibes, all types of shit,” he explains. Great John will be on the beat, among other producers.

Sleepy and Sheff, one of Brooklyn’s finest pairings, also have a collab in the tuck that was being readied until Sheff received a two-year prison bid last November. “It’s still coming though,” Sleepy affirms. “We got some shit in the vault.”

With plenty of ammo in the chamber, Sleepy is poised to continue etching his name into New York City’s golden rap lineage in the same standout fashion of his predecessors. In the meantime, you can catch him in the air where the stars lay.

Sky’s the limit.

Read the cover story with Playboi Carti and check out the other interviews in the magazine with Fivio Foreign, Latto, DaBaby, Wiz Khalifa and Juicy J, Joey Bada$$Denzel Curry, Hit-Boy, Big K.R.I.T.RZA, Saba, Morray, Kali, Sleepy Hallow, Nardo WickATL Jacob, SSGKobe, Pink Sweat$, Saucy Santana, Jason Lee, Angie Randisi and Colby Turner in the new issue of XXL magazine, which is on newsstands now and in XXL's online shop.

See Playboi Carti's XXL Magazine Spring 2022 Cover Story Exclusive Photos

More From XXL