Born in Vancouver, Craig moved to Toronto at the age of 3. Before he ever picked up a guitar, he sang in high school cover bands. In 2007, along with Erik Alcock, Craig formed the band We Are The Take, recording their would-be debut album with Grammy-award winning producer David Bottrill. The band eventually split at the end of 2010, allowing Craig to shift his focus to his own material.

Craig's journey into a solo career has most recently led to signing with veteran music manager Chris Smith of 21 Music. His work has been featured on national and international campaigns such as McDonald's, Tim Horton's and Muller Yogurt. Craig has also appeared in several movies and TV shows such as Scott Pilgrim vs. The World, Being Erica, Lost Girl and Degrassi: The Next Generation. He alternates between playing guitar, piano and the harmonica at his shows but also plays bass and trumpet.