Chuckyy, the 19-year-old rapper from Chicago is rapidly emerging as one of the most interesting new voices in rap. Known for his dark, minimalist approach, he expertly fuses haunting, skeletal production with intricately-delivered verses that showcase his raw lyrical prowess. Tracks like “KingTut” and “Me Vs Me” highlight his ability to craft tension and atmosphere, with his stoic delivery and razor-sharp rhyme schemes setting him apart.
Fresh off the release of his highly-anticipated mixtape I Live, I Die, I Live Again and his first-ever Billboard Hot 100 charting single, “My World”(21M+ streams), rising Chicago rap phenom Chuckyy has just unveiled the official video for “Hiccup”. The two-and-a-half-minute video captures a snapshot of the lifestyle that Chuckyy has sling-shotted himself into, bringing his authentic lyrics to life and reinforcing everything that has made him one of 2025’s most compelling new voices. At just 19 years old and only two years into his rap journey, Chuckyy has delivered one of this year’s most cohesive and ambitious bodies of work — I Live, I Die, I Live Again. The mixtape is a powerful odyssey showcasing his rapid-fire flow, sharpened penmanship, and masterful sequencing, and it was met with immediate critical acclaim from Pitchfork(7.0), The FADER, and XXL. Chuckyy‘s left-field structure and sonic ingenuity make the 11-track release feel like a true statement piece, marking a new chapter in the young prodigy’s fast-moving ascent. I Live, I Die, I Live Again arrives following a string of breakout records, including the Young Jeezy-borrowing heater “We Got Buttons”, “N***a Poetry”, which was hailed by The FADER as one of the best rap songs of March, and “FREE SMURK OFNG” which peaked at #6 Trending on YouTube. Maintaining the eerie, mystical energy that first sparked global intrigue, I Live, I Die, I Live Again expands Chuckyy’s world with newfound depth and introspection. As he pushes deeper into 2025, Chuckyy’s cult-like following, creative drive, and storytelling have made it abundantly clear –– this is only the beginning for the Chicago star.
Known for his horror-themed aesthetics and raw lyricism, Chuckyy has rapidly gained traction in the global rap landscape, amassing a fervent fanbase since his first release, “Bail Out”, in 2023. His 2024 single “Bumblebee” was lauded by Pitchfork as a “bone-chilling mood piece”, highlighting his phantomish flow –– which was quickly co-signed by Chicago powerhouse Lil Durk. Over the past year, Chuckyy has been making waves with a series of compelling releases, including Tweak Till The End and Blood Bathh Vol 1., each showcasing his versatility and fresh take on the classic drill formula. Chuckyy‘s commitment to his craft and exceptional style are positioning him amongst Hip-Hop’s most promising talents.
Drawing from Chicago’s legendary drill roots and the eerie, hypnotic sounds of Philly rap, Chuckyy is both honoring the genre’s legacy and fearlessly pushing its boundaries into uncharted territory. His ability to balance raw street narratives with a surreal sound gives his music a unique edge while blending a style of grit with innovation. As he continues to refine his artistry, Chuckyy is positioning himself as a future leader in the ever-evolving rap landscape.
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