Sleepy Hallow has built one of the most impressive catalogs in Brooklyn drill — a genre-defining body of work that spans viral hits, collaborative anthems, and critically noted projects. As of 2026, his streaming numbers tell the story of an artist who turned underground buzz into mainstream staying power.
Here is a complete breakdown of Sleepy Hallow’s songs, albums, streaming milestones, and what they mean for his estimated $4 million net worth.
Walk Through the Article
Sleepy Hallow: Quick Profile
| Category | Details |
|---|---|
| Real Name | Tyan Walker |
| Born | September 14, 2000 |
| Origin | Brooklyn, New York (Flatbush) |
| Genre | Brooklyn Drill |
| Net Worth (2026) | $4 Million (estimated) |
| Record Label | Winners Circle Entertainment / Epic Records |
| Nationality | American |
Sleepy Hallow’s Biggest Songs
From his earliest releases to his most recent projects, these tracks have defined his career and contributed the most to his streaming income:
1. “2055” (2020)
Arguably Sleepy Hallow’s most recognized track, “2055” became a viral phenomenon on TikTok and major streaming platforms. The song’s haunting melody over drill-influenced production captured a massive audience beyond the typical drill fanbase. Its viral reach helped push his monthly listener count to new heights and remains his highest-streamed track.
2. “Deep End Freestyle” (2020)
This freestyle helped establish his credibility in the New York rap scene. The raw delivery and storytelling earned him widespread respect from both fans and peers, and the track became a staple of his live sets.
3. “Tip Toe” with Sheff G (2020)
The Sheff G collaboration “Tip Toe” showcased the chemistry between the two Brooklyn artists and became one of the most-streamed drill records from New York in 2020. The track’s crossover success helped both artists expand their fanbases beyond the tri-state area.
4. “Jiggy in Jersey” (2021)
Released as part of his growing catalog, this track demonstrated his ability to evolve his sound while staying true to his drill roots. It continued to build his streaming portfolio.
5. “Still” (2021)
Featuring introspective lyrics over melodic drill beats, “Still” resonated with fans who connected with his more emotional side — a quality that distinguishes him from many peers in the genre.
Albums & Projects
Don’t Sleep (2021) — Debut Album
Sleepy Hallow’s debut album Don’t Sleep was released through Winners Circle Entertainment and Epic Records in 2021. The project received positive reviews for its cohesive production and Sleepy Hallow’s melodic sensibility. It featured collaborators including Sheff G and other New York artists. The album charted on the Billboard 200, marking a significant milestone for a Brooklyn drill artist.
Sincerely Tyan (2023)
His second studio album represented artistic growth, with more personal subject matter and expanded production styles. The project showcased his willingness to experiment while maintaining his core drill identity.
Streaming Milestones & Earnings
As of 2026, Sleepy Hallow’s catalog has accumulated hundreds of millions of streams across Spotify, Apple Music, YouTube, and Tidal. At standard streaming royalty rates for established artists (approximately $0.003–$0.005 per stream), his catalog generates meaningful passive income monthly.
His YouTube channel, featuring official music videos and live performances, contributes additional ad revenue. “2055” alone has accumulated tens of millions of views, generating significant royalty income over its lifecycle.
Live Performance Income
Touring and live performances represent a substantial portion of Sleepy Hallow’s income. As his profile has grown, his booking fees have climbed accordingly. Artists at his level in 2026 can command anywhere from $20,000 to $75,000+ per show, depending on the venue size and event type. His live presence — known for high-energy performances that resonate with loyal fans — has made him a sought-after act across festival circuits and club shows.
Early Life and Rise From Jamaica, Queens
Born on December 20, 1999, in Jamaica, Queens, New York, Sleepy Hallow grew up immersed in the sounds that would later define his career. While Brooklyn drill as a genre takes its name from the borough where it crystallized, Sleepy Hallow’s roots in Queens gave him a slightly different perspective — one that he channeled into a melodic approach that set him apart from peers who leaned more heavily on aggressive delivery.
His early career began gaining traction around 2019 when he linked up with fellow rapper Sheff G. The two formed a creative partnership through Winners Circle Entertainment that would prove foundational for both artists. Their collaborative tracks helped establish a template for the Brooklyn drill sound that blended UK drill influences with distinctly New York energy and melodic hooks.
Before signing with RCA Records, Sleepy Hallow built his following through mixtapes like Don’t Sleep (2019) and Sleepy for President (2020). The latter contained “Deep End Freestyle,” the breakout single that caught mainstream attention and climbed to number 80 on the Billboard Hot 100 — a significant achievement for an independent drill artist at the time.
Net Worth Breakdown: Where the $4 Million Comes From
Sleepy Hallow’s estimated $4 million net worth in 2026 draws from several interconnected revenue streams. Music streaming represents the largest share, with his catalog generating hundreds of millions of plays across Spotify, Apple Music, and YouTube. His most successful single, “2055,” achieved double platinum certification and charted internationally — reaching number 13 in Australia and number 11 in New Zealand — generating substantial royalty income that continues to accumulate years after release.
His deal with RCA Records, secured after the success of “Deep End Freestyle,” provided both an advance and ongoing royalty structure typical of major-label contracts for emerging hip-hop artists. Two studio albums — Still Sleep? (2021) and Boy Meets World (2023) — along with his earlier mixtapes, form a catalog deep enough to produce consistent passive income from streaming platforms.
Live performances represent another significant income source. As Brooklyn drill expanded from a local phenomenon to a nationally recognized subgenre, demand for drill artists at festivals, club shows, and university events grew considerably. Artists at Sleepy Hallow’s level of recognition typically command appearance fees ranging from $15,000 to $50,000 per show, depending on the venue and event scale.
Collaborations and Industry Impact
Beyond his solo work, Sleepy Hallow’s collaborative output has been central to his career trajectory. His partnership with Sheff G produced some of Brooklyn drill’s most recognized tracks, and features with artists like Fousheé on “2055” helped bridge the gap between drill’s harder edges and mainstream pop sensibilities.
His influence on the genre extends beyond chart performance. Sleepy Hallow’s melodic approach to drill — layering singing and harmonies over the genre’s characteristic sliding bass patterns — helped open a lane that numerous artists have since followed. While UK drill originators like Pop Smoke (to whom Sleepy Hallow is often compared) emphasized raw intensity, Sleepy Hallow demonstrated that drill production could support genuine melody without losing its edge.
The Winners Circle Entertainment collective, co-founded with Sheff G, also represents an entrepreneurial dimension to his career. By building their own infrastructure rather than simply signing as individual artists, both rappers positioned themselves to capture a larger share of revenue from their music and the artists they develop.
Frequently Asked Questions About Sleepy Hallow
What is Sleepy Hallow’s most streamed song?
“2055” is widely considered Sleepy Hallow’s most streamed and recognized song. The track went viral on TikTok and accumulated tens of millions of streams across platforms.
How many albums does Sleepy Hallow have?
As of 2026, Sleepy Hallow has released two studio albums: Don’t Sleep (2021) and Sincerely Tyan (2023), plus numerous singles and collaborative projects.
What record label is Sleepy Hallow signed to?
Sleepy Hallow is signed to Winners Circle Entertainment in partnership with Epic Records, a deal that has given him major label distribution while maintaining artistic independence.
How much does Sleepy Hallow earn per show?
While exact figures are not publicly confirmed, artists at his level typically earn between $20,000 and $75,000 per performance depending on venue size, market, and event type.
Is Sleepy Hallow from Brooklyn?
Yes, Sleepy Hallow (real name Tyan Walker) is from the Flatbush neighborhood of Brooklyn, New York. His Brooklyn roots are central to his identity as an artist and to the Brooklyn drill genre he helped popularize.
Sleepy Hallow’s Net Worth Over Time
Sleepy Hallow’s financial growth mirrors the trajectory of Brooklyn drill itself. In 2019, when he released Don’t Sleep as a largely unknown artist, his earnings were minimal — typical of an independent rapper building a local following. The breakthrough came in 2020 with “Deep End Freestyle,” which led to the RCA Records deal and a significant jump in both income and profile.
By 2021, with “2055” achieving double platinum certification and Still Sleep? performing well commercially, his net worth likely crossed the $1 million mark. The years since have seen steady accumulation through catalog royalties, touring revenue, and his role in Winners Circle Entertainment. His estimated $4 million net worth in 2026 reflects consistent output across albums, singles, and live appearances rather than any single massive payday.
Final Take: Sleepy Hallow’s Musical Legacy in 2026
At just 25 years old, Sleepy Hallow has compiled a catalog that most artists spend a decade trying to build. His songs — particularly “2055” and his Sheff G collaborations — have defined the Brooklyn drill sound for a generation of listeners. With two studio albums, hundreds of millions of streams, and a live performance circuit that continues to grow, his $4 million net worth in 2026 reflects a career built on consistent output and undeniable talent.
The next chapter of Sleepy Hallow’s career looks promising. As Brooklyn drill continues to influence global hip-hop, he remains one of the genre’s most compelling voices.
