Tegan Joshua Anthony Chambers, better known by his stage name Sleepy Hallow, has become a prominent figure in the hip-hop world, particularly within the Brooklyn drill scene. As of 2025, Sleepy Hallow’s net worth is a topic of great interest among fans and industry observers, reflecting his rapid rise from the streets of Flatbush, Brooklyn, to mainstream success. Estimates of Sleepy Hallow’s net worth in 2025 vary, with figures ranging from $2 million to $7 million, depending on the source.
Early Life and Beginnings in Music
Born on December 20, 1999, in Jamaica, Tegan Chambers immigrated to the Flatbush neighborhood of Brooklyn, New York, as a young child. Growing up in a vibrant but challenging environment, he was exposed to the realities of inner-city life, which later influenced his music. Chambers adopted the moniker “Sleepy Hallow,” a nod to his street name and a playful reference to Washington Irving’s The Legend of Sleepy Hollow. The “Hallow” spelling, with an “A,” adds a Halloween-inspired flair, reflecting his unique persona in the rap game.
Sleepy Hallow began rapping at the age of 12, honing his craft alongside underground artists in Brooklyn. He dropped out of school in the ninth grade, choosing to pursue music full-time. His early years were marked by a fateful encounter with fellow rapper Sheff G, who would become a frequent collaborator and close friend. The two initially met under tense circumstances, preparing to fight, but bonded over mutual respect, laying the foundation for their musical partnership.
Breakthrough in the Music Industry
Sleepy Hallow’s entry into the professional music scene came in 2017 when he and Sheff G signed with Nula Entertainment, a label owned by former NFL player Junior Galette. Their first major hit, the 2018 single “Flows,” featuring Sheff G, went viral, introducing Sleepy Hallow to a broader audience. In 2019, he released his debut mixtape, Don’t Sleep, under Winners Circle Entertainment, a label he co-founded with Sheff G after leaving Nula Entertainment. The mixtape showcased his signature melodic flow and introspective lyrics, cementing his place in the Brooklyn drill movement.
The year 2020 marked a turning point for Sleepy Hallow’s net worth in 2025. His single “Deep End Freestyle,” featuring Fousheé, became a massive hit, earning platinum certification from the Recording Industry Association of America (RIAA) and peaking at number 80 on the Billboard Hot 100. With over 85 million streams and international popularity on platforms like TikTok, the track significantly boosted his earnings through streaming royalties and social media exposure. That same year, Winners Circle Entertainment partnered with RCA Records, providing Sleepy Hallow with a larger platform to showcase his talent.
In 2021, Sleepy Hallow released his debut studio album, Still Sleep?, which included the hit single “2055.” The song peaked at number 51 on the Billboard Hot 100 and was certified double platinum in 2022, further contributing to his growing wealth. Tracks like “Die Young” (featuring 347aidan) and “2 Mins of Pain” continued to showcase his versatility, blending hard-hitting beats with emotional storytelling. His 2023 album, Boy Meets World, featured collaborations with artists like Marshmello and Doechii, reinforcing his ability to evolve as an artist while maintaining his drill roots.
Estimating Sleepy Hallow’s Net Worth in 2025
As of 2025, Sleepy Hallow’s net worth is estimated to range between $2 million and $7 million, with variations across sources. For instance, Net Worth Spot estimates his net worth at around $4 million, while CAknowledge suggests a higher figure of $7 million. These discrepancies arise due to differing methodologies and the inclusion of various income streams. Let’s break down the key contributors to Sleepy Hallow’s net worth in 2025.
1. Music Sales and Streaming Royalties
Sleepy Hallow’s primary source of income comes from his music career, including album sales, streaming royalties, and digital downloads. Hits like “Deep End Freestyle” and “2055” have amassed millions of streams on platforms like Spotify, Apple Music, and YouTube, generating significant revenue. For example, his YouTube channel, with over 1.5 million subscribers and 1.2 billion video views as倦System: views as of 2025, earns approximately $1.21 per 1,000 views, contributing to a monthly income of around $14,000–$15,200.
2. Live Performances and Tours
Live performances are a major revenue stream for Sleepy Hallow. His high-energy concerts and festival appearances, such as Rolling Loud and Hot 97’s Summer Jam, attract large audiences, generating income through ticket sales and merchandise. Fans have praised his engaging stage presence and interaction with crowds, which enhances his marketability as a live performer. His 2025 tour with Sheff G, Winners Circle In Your City Tour, includes stops in cities like Cleveland, Los Angeles, and Tucson, further boosting his earnings.
3. YouTube and Social Media
Sleepy Hallow’s YouTube channel is a significant income source, with monetized videos earning $3–$7 per 1,000 views. With over 1.2 billion total views and 124 uploaded videos, his channel generates substantial ad revenue. Additionally, his social media presence on platforms like Instagram (781K followers) and Twitter (34K followers) allows him to earn money through brand promotions and sponsored content.
4. Merchandise and Brand Ventures
As part of Winners Circle Entertainment, Sleepy Hallow sells branded merchandise through the label’s official website, including clothing and accessories. These sales contribute to his overall net worth, though specific figures are not publicly available.
Challenges and Controversies
Despite his success, Sleepy Hallow has faced significant challenges that could impact his net worth. In May 2023, he was charged in a 140-count indictment alongside 32 alleged gang members, including Sheff G, for gang-related conspiracy charges linked to multiple shootings. While he was released after serving a seven-month sentence for illegal weapons possession, these legal issues may have incurred substantial legal fees and temporarily halted his music production. However, his release of Boy Meets World in September 2023 and subsequent singles in 2024 demonstrate his resilience and ability to continue building his career.
Additionally, Sleepy Hallow’s public support for Donald Trump’s 2024 presidential campaign, including attending a rally in the Bronx, sparked controversy among some fans. While this may have affected his public image, his loyal fanbase continues to support his music, mitigating potential financial losses.
Personal Life and Lifestyle
Sleepy Hallow keeps his personal life relatively private, but he is known to be a father to a daughter named Melina with his partner Dreaa Banks. His social media posts occasionally feature his daughter, reflecting a personal side that resonates with fans. Despite his wealth, Sleepy Hallow maintains a relatively modest lifestyle compared to some rappers, focusing on his music and family. His net worth allows him to afford luxury items, but specific details about his car collection or home are scarce.
The Future of Sleepy Hallow’s Net Worth in 2025 and Beyond
Looking ahead, Sleepy Hallow’s net worth in 2025 is expected to grow as he continues to release new music and expand his brand. His recent singles, such as “Yes Freestyle” with Sheff G and “MARGARET,” released in early 2025, indicate a steady output of content that keeps him relevant in the competitive hip-hop industry. Collaborations with high-profile artists and producers, such as Marshmello, and his ability to adapt his sound to broader audiences suggest a promising financial trajectory.
Moreover, his partnership with RCA Records and Winners Circle Entertainment provides a strong foundation for future projects. The label’s focus on Brooklyn drill and its growing influence in the industry could lead to more lucrative deals and opportunities. If Sleepy Hallow continues to avoid legal entanglements and maintain his creative momentum, his net worth could approach or exceed the higher estimates in the coming years.
Why Sleepy Hallow’s Net Worth Matters
Sleepy Hallow’s net worth in 2025 is more than just a number; it represents the culmination of his talent, hustle, and resilience in the face of adversity. From his humble beginnings in Flatbush to becoming a platinum-certified artist, his journey reflects the potential for success in the modern music industry. His ability to generate income through multiple streams—music sales, streaming, live performances, YouTube, and merchandise—demonstrates a savvy approach to building wealth.
For fans and aspiring artists, Sleepy Hallow’s story is a testament to the power of authenticity and perseverance. His music, characterized by hard-hitting beats and introspective lyrics, resonates with a generation navigating similar challenges. As he continues to push the boundaries of Brooklyn drill and expand his influence, Sleepy Hallow’s net worth in 2025 serves as a benchmark for his achievements and a glimpse into his future potential.
Conclusion
Sleepy Hallow’s net worth in 2025, estimated between $2 million and $7 million, reflects his meteoric rise in the hip-hop world. From his breakout singles “Flows” and “Deep End Freestyle” to his chart-topping hit “2055,” he has built a lucrative career through music sales, streaming royalties, live performances, and YouTube revenue. Despite facing legal challenges and controversies, Sleepy Hallow remains a resilient and innovative artist, continuously evolving his sound and brand. As he embarks on new projects and tours in 2025, his net worth is poised to grow, solidifying his status as a leading figure in the Brooklyn drill scene and a rising star in global hip-hop.
