Skyzoo’s career is a story of determination, lyricism, and a deep connection to the roots of Hip Hop. Born Gregory Skyler Taylor in Crown Heights, Brooklyn, Skyzoo was raised in nearby Bedford-Stuyvesant, one of the most iconic neighborhoods in Hip Hop history. His passion for rap started at a young age, inspired by local legends like The Notorious B.I.G. and Jay-Z. By age nine, he was already writing rhymes, a practice that laid the foundation for his eventual rise in the underground scene.
In the early 2000s, Skyzoo began making a name for himself through mixtapes and independent projects, blending his intricate wordplay with beats that leaned heavily into the boom-bap tradition. His big break came when he connected with 9th Wonder and the Justus League, leading to their collaborative project, Cloud 9: The 3 Day High (2006). Produced entirely by 9th Wonder, the album was recorded in just three days, but its quality and cohesion stood out, proving Skyzoo’s ability to craft thoughtful narratives in a short amount of time. The project set the tone for the rest of his career—Skyzoo established himself as an artist who prioritized lyricism and storytelling, creating music that resonated with listeners who craved substance in their Hip Hop.
His debut solo album, The Salvation (2009), was a turning point. Released through Duck Down Records, the album featured production from heavyweights like Just Blaze, 9th Wonder, and Nottz. It was a deeply personal record, showcasing Skyzoo’s ability to weave his life experiences into rich, vivid narratives. Songs like “The Beautiful Decay” and “My Interpretation” highlighted his knack for introspection, tackling themes of ambition, struggle, and identity. The album not only established his presence in the underground but also hinted at the broader potential of his artistry.
Skyzoo continued to build on this momentum with subsequent projects like Live From The Tape Deck (2010), a collaboration with producer !llmind, and A Dream Deferred (2012), which expanded his sonic palette while diving deeper into his storytelling roots. Along the way, he collaborated with respected names like Black Thought, Talib Kweli, and Jill Scott, earning a reputation as a lyricist’s lyricist.
In 2014, Skyzoo teamed up with Torae to form the duo Barrel Brothers, resulting in an album that paid homage to New York’s rich rap history while delivering hard-hitting tracks and sharp lyricism. The chemistry between Skyzoo and Torae was evident, and the project added another layer to Skyzoo’s already diverse discography. Their partnership exemplified the collaborative spirit of Hip Hop, emphasizing lyrical prowess and mutual respect.
This commitment to growth was evident in projects like Music For My Friends (2015), which explored the intersections of childhood, friendship, and survival, and The Easy Truth (2016), a collaborative effort with Detroit producer Apollo Brown that paired Skyzoo’s reflective rhymes with gritty, soulful beats, and other strong records like In Celebration of Us (2018), All the Brilliant Things (2021), and The Mind of a Saint (2023).
One of Skyzoo’s absolute best works is his 2019 collaboration with legendary producer Pete Rock on Retropolitan. This project was a love letter to New York City, blending Skyzoo’s vivid storytelling with Pete Rock’s classic, soulful production. The album highlighted the cultural and musical heritage of their hometown, reinforcing Skyzoo’s role as a custodian of Hip Hop’s rich traditions. Skyzoo’s earlier career not only laid the groundwork for his unique sound but also established him as one of the most consistent voices in Hip Hop.
His respect for the culture and commitment to authentic storytelling shines through in every project, and Keep Me Company feels like the natural evolution of a career built on honesty, craftsmanship, and an unwavering love for the art form.
Keep Me Company feels like an intimate conversation, filled with honesty, wisdom, and moments of quiet reflection. Throughout the album, Skyzoo moves with a calm assurance, piecing together stories and observations in his signature lyrical style. The music flows effortlessly, grounded in jazz-inspired boom bap, creating a sound that feels timeless yet undeniably personal. It’s the kind of album that draws you in slowly, pulling you deeper with every listen, revealing layers that aren’t always immediately apparent.
The album opens with “Community Service,” a jazzy, thought-provoking track that feels like setting the table for what’s to come. The horns swirl over a steady beat, while Skyzoo’s voice carries a weight that makes you hang on every word. He dives into themes of unity and the unspoken connections between people, but there’s no preaching here—his words feel conversational, almost like he’s speaking directly to you. JRose’s spoken word outro ties the track together, adding another layer of warmth and depth.
From there, Keep Me Company keeps the mood rich and textured. Tracks like “Finder’s Keepers” and “Home Away From Home” lean heavily into the jazz influence, with instrumentation that feels alive, almost breathing alongside Skyzoo’s words. “Finder’s Keepers” carries a sense of determination, as Skyzoo talks about pursuing what’s his with a focus and energy that’s palpable. “Home Away From Home,” on the other hand, feels more introspective, reflecting on relationships and the kind of connections that endure even when distance gets in the way. The beats are subtle but effective, giving Skyzoo’s lyricism all the room it needs to shine.
“Drug Free School Zone” shifts gears slightly, bringing in a rawer, more stripped-back production style. Here, Skyzoo reflects on responsibility and legacy, his words painting a picture of someone trying to build something lasting in the face of constant challenges. The song has a certain quiet intensity, with each verse feeling like it’s been carefully thought through, down to the last detail. This kind of meticulousness defines much of the album—nothing feels rushed or out of place.
As the album progresses, the balance between the personal and the universal becomes more apparent. Tracks like “Prayers for the Customers” and “Courtesy Call” show Skyzoo’s ability to take everyday observations and turn them into something meaningful. “Prayers for the Customers” has an almost meditative quality, the jazz elements wrapping around Skyzoo’s words as he warns against the dangers of false alliances. Meanwhile, “Courtesy Call” brings in Chuck D for a commanding feature, as the two artists exchange wisdom about the stakes of life and the consequences of every decision. The stripped-down beat here gives the song a rawness that’s impossible to ignore.
“Record Store Day” offers a lighter, more playful moment, as Skyzoo spins a narrative about love, vinyl culture, and fleeting connections. The jazzy backdrop is the perfect accompaniment, making the track feel as cozy as flipping through records in a small shop. It’s a standout for its charm and relatability, showing Skyzoo’s range without ever straying from the album’s core themes.
Keep Me Company’s tone becomes even more introspective as it moves toward its final tracks. “Sleeping Beauty” is haunting in its simplicity, with Skyzoo reflecting on how presence can often speak louder than words. It’s a song that lingers, the kind that stays in your mind long after the music stops. Similarly, “Wins of the Father” is deeply personal, an open letter to Skyzoo’s child that explores what it means to be both proud and grateful. The production here is understated but powerful, allowing the emotion in Skyzoo’s voice to carry the weight of the song.
The album closes with “Jazz in the Projects,” an eight-minute finale that feels like both a summary and a statement. Over a lush, jazzy beat, Skyzoo reflects on growth, survival, and the unspoken battles we all fight. It’s an ambitious track, but it never feels overindulgent. Instead, it wraps the album up with a sense of quiet triumph, leaving you with the impression that Skyzoo has said everything he needed to say, exactly how he wanted to say it.
What makes Keep Me Company so compelling is its honesty. Skyzoo isn’t trying to reinvent himself or the genre; instead, he’s refining what he does best—telling stories that feel personal but resonate on a larger scale. The production, rooted in jazz and boom bap, gives the album a cohesive sound without ever feeling repetitive. Each track feels intentional, with Skyzoo’s words and the music working in harmony to create something greater than the sum of its parts.
This is the kind of album that grows with you. It doesn’t demand your attention right away; instead, it invites you to sit with it, to take your time and really listen. And when you do, you realize how much care and thought went into every aspect of it. Keep Me Company is Skyzoo at his most reflective, creating a space where vulnerability and strength exist side by side.
8.5/10
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