7 Deepest Truths You Learn When You Listen To Sleepy Hallow's "A N X I E T Y" (Feat. Doechii)

The search query "listen to sleepy hallow anxiety" is more than just a request for a track—it’s a gateway into one of the most raw, introspective, and commercially successful songs in the current hip-hop landscape. As of today, December 18, 2025, the track "A N X I E T Y" remains a standout single from Sleepy Hallow’s 2023 album, Boy Meets World, resonating deeply with millions due to its unflinching look at mental health struggles and the complex pressures of fame. This article dives into the song's unique history, its profound lyrical content, and the creative collaboration that made it a viral phenomenon, offering a fresh analysis for both new listeners and dedicated fans.

The track, which features the dynamic talent of Doechii, transcends the typical Brooklyn Drill sound Sleepy Hallow is known for, offering a vulnerable, melodic exploration of the internal "demons" that plague the human mind. Its powerful message and unconventional path to mainstream success—rooted in a viral sample—make it a crucial listen for understanding modern rap's evolving relationship with emotional transparency.

Sleepy Hallow: Biography and Profile

Tegan Joshua Anthony Chambers, known professionally as Sleepy Hallow, is a Jamaican-American rapper and singer-songwriter who has become a leading figure in the melodic side of the Brooklyn Drill scene.

• The Untouchable Privacy 7 Secrets Of Rachel Mcadams And Jamie Lindens Life Beyond The Red Carpet E820e

• Full Name: Tegan Joshua Anthony Chambers
• Stage Name: Sleepy Hallow
• Date of Birth: December 20, 1999
• Place of Birth: Jamaica
• Hometown/Upbringing: Flatbush, Brooklyn, New York City
• Genre: Hip Hop, Drill, Melodic Rap
• Associated Acts: Sheff G, Great John (Producer)
• Breakthrough Hit: "2055" (2021)
• Notable Albums: Sleepy For President (2020), Still Sleep? (2021), Boy Meets World (2023)

After emigrating from Jamaica, Chambers settled in Flatbush, where he began his musical journey, often collaborating with his childhood friend and fellow rapper, Sheff G, and the influential producer Great John.

The Unconventional History of "A N X I E T Y": A TikTok Origin Story

The journey of "A N X I E T Y" is one of the most fascinating examples of how social media can reshape the music industry. The song's core sound and structure are built on a unique sample, creating a piece of musical "lore" that adds significant depth for listeners.

1. The Doechii Sample: A Viral Foundation

The track is not a traditional collaboration but a brilliant use of a sample. The song features a key vocal snippet from rapper and singer Doechii’s original, unreleased track, also titled "Anxiety." Doechii had originally freestyled the song in her Coven Music Sessions back in 2019.

• Shania Twains Bold Statement Why The Star Chose Nude Photoshoots At 57 Qf9cg

Sleepy Hallow and his production team, led by Great John, recognized the power of Doechii's raw, emotional hook and sampled it for his track. This creative sampling led to Sleepy Hallow's version "blowing up," particularly on platforms like TikTok.

2. The "Lore" That Forced an Official Release

The viral success of Sleepy Hallow's track created a massive demand for the original Doechii vocal. Before the collaboration became official, many listeners were unaware of the sample's origin. Doechii herself had to break down the "lore" of the song for fans, explaining that Sleepy Hallow's track was a sample that had gained so much traction it essentially forced the original version to be officially released for streaming. This unique, circular path highlights a new dynamic in music creation and consumption.

The official release of Sleepy Hallow's "A N X I E T Y" featuring Doechii came on September 15, 2023, as part of the Boy Meets World album, solidifying its place as a commercial and critical success.

• The Unseen Story Jessica Simpsons Battle For Privacy And Body Image In A Digital Age Mlvqa

Diving Deep Into the Lyrics: 5 Themes of Mental Struggle

For those who "listen to sleepy hallow anxiety," the immediate takeaway is the rapper's willingness to be profoundly vulnerable. Unlike much of the boastful or narrative-driven hip-hop, this track serves as a direct, lyrical journal entry detailing his internal battles. Sleepy Hallow opened up about the track's meaning on Genius Verified, confirming its personal nature.

3. Wrestling with Relentless Demons

The central theme of the song is the struggle against internal "demons"—a metaphor for his relentless mental health issues. Sleepy Hallow describes feeling "lost in this maze," indicating a sense of entrapment and confusion that is characteristic of severe anxiety. The lyrics paint a picture of a man wrestling with his mind, a fight that never truly ends.

4. The Pressure of Success and Fame

While the song is about anxiety, it's specifically about the anxiety that comes with a high-stakes career. Sleepy Hallow is a major artist in the Brooklyn Drill scene, and his success brings intense pressure. The lyrics subtly touch on the paranoia and stress that accompany fame, where every decision is scrutinized and the stakes are constantly rising. This context adds a layer of topical authority to the track, connecting the personal to the professional.

5. Isolation and Inability to Trust

A common thread in the track is a feeling of isolation. Anxiety often pushes people away, making trust difficult. The song explores the paranoia that comes with success—the fear of who is genuine and who is only around for the money or fame. This sense of being guarded and unable to fully relax or trust anyone is a critical component of his mental maze.

6. The Melodic Contrast: Drill Meets Introspection

Produced by the prolific Great John, the beat itself is a masterclass in modern melodic rap. It retains a subtle rhythmic intensity, hinting at the drill origins, but is softened by a melodic, almost haunting backdrop. This musical contrast perfectly mirrors the lyrical content: the external world (the beat) is calm, but the internal world (the lyrics) is chaotic and intense. This production choice is why the song resonates beyond the typical drill fanbase.

7. A New Benchmark for Emotional Transparency in Hip-Hop

"A N X I E T Y" is not just a great song; it's a cultural marker. Along with his other introspective hit, "2055," this track solidifies Sleepy Hallow's role as an artist willing to normalize conversations about mental health in a genre often criticized for prioritizing toughness and bravado. By laying his mental struggles bare, he provides a powerful form of validation and connection for his listeners, turning a personal battle into a shared experience. This emotional transparency is a key reason why the track continues to gain new listeners and maintain its popularity across streaming platforms.

For anyone looking to understand the evolution of the Brooklyn sound or seeking a deeply personal, melodic track that speaks to the modern condition, "A N X I E T Y" is essential listening. The track’s unique backstory with Doechii, combined with Sleepy Hallow’s raw delivery, makes it a timeless piece of contemporary hip-hop.