Sleepy Hallow finished out 2020 on a high note fittingly alongside his Flatbush compatriot Sheff G. The dynamite Brooklyn duo put the turbulent year in perspective while narrating their grimy come-ups alongside Hot 97’s DJ Drewski on the single “2020 Vision.”

With all eyes on the Brooklyn drill scene as the en vogue sound dominating Hip Hop that everyone wants a piece of, it’s time for Sleepy to make the quantum leap and snatch a seat at the table in 2021, making him a prime candidate for the HipHopDX Rising Stars 2021 class!

Hometown: Brooklyn, NY

Notable Co-Signs: Fivio Foreign, Lil Tjay, Benny The Butcher

Notable Projects To Date:Sleepy For President (2020)

Accolades To Date: “Deep End Freestyle” became certified gold in August 2020 and peaked on the Hot 100 at No. 80; 4.4 million monthly Spotify listeners; Signed to RCA in 2020 alongside Sheff G

[This post has been updated. The following was originally published on February 4, 2021] Read updates below.

Musical Style

Sleepy keeps his menacing drill rhymes short but still packs an exhilarating punch. The 21-year-old plays it close to the vest with his coy interviews and his hat tilted to the side, often letting his music do most of the talking for him, unlike a lot of his college-aged Hip Hop compatriots.

With a keen ear for production, Sleepy understands song-building and what sounds best complement his rugged flow, which is often brought out of him when working alongside Winners Circle producer Great John. For example, give his ominous Sheff G collab “Tip Toe” a listen. The frightening sample that would be best suited for a horror movie was actually Sleepy’s idea.

“He just walked in with this crazy idea,” Winners Circle manager Jeremy “Jerm” Soto recalled of Sleepy picking out the eerie sample in an interview with Complex. “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.”

Rising Star Power

Since the death of Pop Smoke, the drill throne has been for the taking and it’s only a matter of time before one of the noted Brooklyn rappers in the same lane asserts themselves in the mainstream’s spotlight.

Instead of jumping into a quick major label deal, Sleepy, who became a father for the first time last year, stayed independent joining Winners Circle Entertainment alongside Sheff G in 2019. He patiently built the necessary buzz around the city with Sleepy For President’s arrival before his team entered negotiations with RCA Records. WCE struck a partnership deal in August 2020 with RCA for Sleepy to go major and he’ll now have the label machine at his back for future releases.

“Winners Circle is not just a clique, they’re a movement,” RCA president Mark Pitts said in a statement coinciding with the deal. “Hip Hop is continuously evolving, and they are ushering in the next wave of the culture. To paraphrase the great [Notorious B.I.G.], that Brooklyn bullshit. They on it!”

A lot can be learned about an artist when they face adversity, and with his Brooklyn upbringing, a certain fearlessness has already been instilled in Sleepy. Long before the days of becoming best friends with Sheff G, Sheff was actually supposed to jump him one day, but Sleepy’s willingness to not back down let Sheff know he was built differently.

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“It was like 50 of us, and he’s by himself walking around the block, and we start screaming at him,” Sheff told HipHopDX. “He dead ass stopped and turned around. So I was like, ‘Yo, wait. I like him. I think this kid on some different shit.’ After that, we ended up always seeing him, so that’s how we first got cool and shit. I know he was on the same type of time as me because if he wasn’t, he would have ran from us that day.”

HipHopDX will continue to watch Sleepy’s moves closely as he heads into his major-label debut. Congratulations to Brooklyn’s own Sleepy Hallow for being a 2021 Rising Star!

Sleepy Hallow is one of 10 up-and-coming rappers named to HipHopDX’s 2021 Rising Stars! For more info on Sleepy Hallow and the rest of the talented Hip Hop bunch, read about them here.


  • Drops “2 Sauce” music video on YouTube
  • Drops official “2055” music video on Youtube currently at 3.7 million views
  • Dropped ‘Still Sleep?’ [June 2]
  • Drops 2-in-1 music video for “Chicken” and “Mi No Sabe”
  • Rap caviar adds “2055” to “Just Added” playlist
  • Sleepy Hallow is recruited to Kendrick Lamar-headline festival Day N Vegas
  • Announced Summer Jam 2021 Festival performance
  • “Deep End (Freestyle)” goes platinum!
  • Performs Rolling Loud Miami


  • Promising album release and then delaying album release