Before his debut album Kindest Regards in 2013 and before his name change, Witt Lowry was recording as Witty and building a grassroot following online. In 2012, he dropped Headphone Hero, a self-released mixtape on DatPiff that gave fans their first sustained look at his blend of high-speed flows, earnest lyrics, and melodic production. Headphone Hero plays like a manifesto of a young artist determined to stand out in an oversaturated scene. With themes of perseverance, self-belief, and creative independence, the project laid the groundwork for the deeply personal style Witt would later refine on Kindest Regards. Though never officially released to streaming platforms, Headphone Hero remains a cult favorite among longtime listeners who discovered him in the mixtape era. The project stands as an early testament to Witt Lowry’s relentless work ethic and connection with fans, a snapshot of an artist in the making, heard first through headphones long before mainstream recognition.