Sleepy Hallow Lyrics – Singles & Featured

English 674 January 1, 2017

Sleepy Hallow, a prominent figure in Brooklyn drill music, emerged from the streets of Flatbush, Brooklyn, after immigrating from Jamaica as a child. His journey into rap began at the age of 12, leading him to adopt the moniker "Sleepy Hallow" as his street name. Despite dropping out of school in ninth grade, his talent and demeanor caught the attention of fellow artist Sheff G during a potential altercation, which ultimately turned into a collaborative partnership.

During 2017 to 2018, Sleepy Hallow, along with Sheff G and DizzyGotBands, found themselves signed to former NFL player Junior Galette's record label, Nula Entertainment. However, it was in 2019 when Sleepy Hallow stepped into the limelight with the release of his debut mixtape, "Don't Sleep." This marked the beginning of his ascent in the rap scene.

The following year, Sleepy Hallow dropped his second mixtape, "Sleepy for President," featuring the breakout hit "Deep End Freestyle" with Fousheé. The track not only peaked at number 80 on the US Billboard Hot 100 but also garnered over 85 million streams, earning a gold certification from the RIAA in August 2020.

As his career progressed, Sleepy Hallow joined forces with Winners Circle Entertainment, which later formed a partnership with RCA Records in August 2020. Together with Sheff G, they released the hit single "Tip Toe," solidifying their presence in the industry.

In June 2021, Sleepy Hallow unveiled his debut studio album, "Still Sleep?," featuring the chart-topping single "2055." The album showcased his versatility and creative vision, earning critical acclaim and commercial success.

Despite facing legal challenges in 2023, including a 140-count indictment, Sleepy Hallow returned to the music scene with resilience. He released his second studio album, "Boy Meets World," on September 15, 2023, featuring collaborations with artists like Marshmello and Doechii.

Continuing his momentum into 2024, Sleepy Hallow dropped the single "Cupid's Guidance" on February 13, further solidifying his position as a force to be reckoned with in the rap world. Below you can find a to z all track details, with lyrics and videos.

Sleepy Hallow (Singles) album Cover

Sleepy Hallow (Singles) album cover

Cast & Crew

  • Artist/Band
  • Years Active
  • January 1, 2017 - Present
  • Producer(s)
  • Sleepy Hallow
  • Writer(s)
  • Sleepy Hallow