After introducing himself to online audiences with his 2012 mixtape Headphone Hero, released under the name Witty, Connecticut rapper Witt Lowry sharpened his craft and vision. In 2013 he followed up with Kindest Regards, a full-length project on DatPiff that would become his breakout moment and solidify his reputation for heartfelt, high-velocity hip-hop. While Headphone Hero revealed a young artist experimenting with sound and narrative, Kindest Regards pushed those elements into sharper focus, cinematic production, rapid-fire flows, and confessional lyrics about ambition, heartbreak, and self-belief. The title track “Kindest Regards” quickly went viral, and along with “Rescue,” remains one of the only two songs from the project officially released on streaming platforms as standalone singles. More than a decade later, Kindest Regards is remembered as the release where Witt Lowry’s voice truly emerged. Building on the raw promise of Headphone Hero, it became both a mission statement and a launching pad, proof that independent, emotionally rap could resonate deeply without industry backing.