Sleepy Hallow has dropped a new single that references and borrows from a familiar R&B hit from the mid-90s.

On Wednesday (February 14), the 24-year-old Brooklyn rapper dropped “Cupid’s Guidance” with an accompanying music video. The vibrant and upbeat joint samples the 112‘s “Cupid,” originally released as part of their self-titled debut album in 1996.



She shot her shot on the ‘Gram/ I can’t be fuckin’ on fans/ Told a baddie ‘hit me’ when she land,” the 2022 HipHopDX Rising Star spits on the song’s chorus.

About his long-term vision for blending pop and drill, the Flatbush native said: “Years from now when they talk about legends, I want to be one of the top names they bring up.”

Watch the music video below:

HHDX YouTube Video Player - Play ButtonYoutube Video - Sleepy Hallow Gets ‘Cupid’s Guidance’ On New 112-Sampling Single

In addition to the new track, Sleepy Hallow is also gearing up to head out on the road for his Boy Meets World Tour, which is set to kick off next month.

Beginning in Hartford, CT on March 22, he’ll also take in shows in Cleveland, New York, Denver, Los Angeles and more, with the trek ending in Phoenix on April 16.

See the full list of dates below — get your tickets here.



MARCH 2024

22 – Hartford, CT – The Webster
23 – Providence, RI – The Strand
24- Worcester, MA – The Palladium
28 – Cleveland, OH- House of Blues
29 – Sayreville, NJ- Starland Ballroom
30 – New York, NY – The Palladium

APRIL 2024

4 – Fort Wayne, IN – Pierre’s
5 – Joliet, IL – The Forge
7 – Denver, CO – Cervantes Other Side
10 – Seattle, WA – Madam Lou’s
11 – Portland, OR – Peter’s Room at Roseland
15 – Los Angeles, CA – Echoplex
16 – Phoenix, AZ – Nile Theater

Eli Fross & Sleepy Hallow Hold It Down For Sheff G With 'Steppas Freestyle' Video
Eli Fross & Sleepy Hallow Hold It Down For Sheff G With 'Steppas Freestyle' Video

Sleepy Hallow is flourishing in the Hip Hop space right now, but he’s had to overcome some hurdles to get here including some legal issues.

Last summer, he was arrested with fellow drill rapper and collaborator Sheff G on conspiracy charges as part of a sprawling 140-count indictment targeting multiple NYC gangs.

According to the New York Post, 32 members from 8 Trey Crips and 9 Ways were charged with murder, illegal possession of weapons, kidnapping, assault and conspiracy. The criminal acts in question allegedly took place from 2019 to 2023.



The District Attorney’s Office stated that those indicted were linked to 27 acts of violence over a four-year span, during which they allegedly used about 37 firearms — 19 had since been recovered by law enforcement at the time of the arrests.