NXT UP: TOBi
TOBi - Courtesy of Jay/3rd.visions
Oluwatobi Feyisara Ajibolade, better known as TOBi, has carved out a distinctive place in contemporary music by blending hip-hop, soul, introspective lyricism and unapologetic vulnerability into a sound that feels both timeless and deeply personal. Born in 1993 in Lagos, Nigeria, TOBi moved to Canada with his family at a young age, eventually settling in Brampton, Ontario, a multicultural suburb of Toronto that would become a key backdrop for his artistic formation.
From early beginnings writing lyrics and poetry, TOBi’s musical journey began with a deep engagement with storytelling and self-reflection. As a youth in Brampton, he participated in battle rap competitions and church choir, sharpening his lyrical skills and vocal presence while navigating questions of identity shaped by immigration, culture and belonging. His early creative impulses were further shaped by a university education in biology and psychology at Wilfrid Laurier University, where music remained his emotional outlet even as he pursued academic studies.
In 2015, TOBi independently released his EP FYI, marking the start of a professional trajectory that would soon intersect with major labels. He signed with RCA Records and Same Plate Entertainment, leading to his label debut Still in May 2019, a deeply vulnerable project exploring themes of self-reflection, the immigrant experience, masculinity and emotional growth. Critics praised the album for its lyrical honesty and genre-fluid approach, and fans responded to TOBi’s ability to articulate inner life with nuance and depth.
TOBi’s follow-ups continued to expand both his sound and his reach. In October 2020, he released Elements Vol. 1, a project characterized by its exploratory sonic palette and evolving introspection, blending rap with soul, melody and thoughtful poetic technique. The project was shortlisted for the Polaris Music Prize and earned him significant critical acclaim, underlining his rising influence in the Canadian music scene.
In 2023, TOBi dropped PANIC, a socially conscious and emotionally resonant album that went on to sweep major categories at the 2024 Juno Awards, including Rap Album of the Year and Rap Single of the Year for Someone I Knew. His ability to fuse lyrical depth with engaging musicality earned praise from major outlets like Billboard, Rolling Stone, i-D, COLORS and Pitchfork, many highlighting his seamless transitions between rap, R&B and soul influences.
In 2025, TOBi continued his creative evolution with Elements Vol. 2, a mixtape that embraces a more liberated, mood-driven approach. Rather than confining itself to a strict narrative, this follow-up reflects his desire to provide music that resonates emotionally with a wide range of life experiences, from introspection and restlessness to celebration and calm, inviting listeners to “sit back and enjoy the highs and lows of life.”
On his most recent collaborative album The Perfect Blue with producer Real Bad Man, TOBi delivers standout tracks that merge his introspective flow with textured, moody production. The project, released in November 2025, features the lead single When I’m Home, a soulful, atmospheric cut that highlights TOBi’s skill at blending rap and singing over elegant, groove-driven soundscapes.
Other notable songs from the album include emotionally resonant pieces like Falling and Over The Moon, which continue the album’s reflective and cinematic vibe. The Perfect Blue showcases TOBi’s evolution beyond traditional rap frameworks, embracing a more expansive, genre-fluid approach that reflects both his roots and creative growth.
Across his career, TOBi’s artistry has been marked by a commitment to emotional sincerity, cultural nuance and communal connection. His work often bridges personal introspection with broader social reflections, addressing issues like identity, vulnerability and the human experience in ways that feel both urgent and universal. Beyond music, he’s also a co-founder of UNPACK Community, an initiative focused on mental wellness within creative spaces, reinforcing his role not just as an artist but as a voice for deeper reflection and shared growth.
As he continues to build on his evolving catalog, from Still to PANIC and beyond, TOBi stands out as a uniquely thoughtful presence in contemporary music, one whose blend of soulful sound, lyrical clarity and emotional honesty points toward a lasting impact on hip-hop, R&B and beyond. His career is a testament to the power of music as a medium for vulnerability, connection and cultural dialogue, a longtime journey still unfolding in meaningful ways.