Born in Toronto, Ontario, Healey was raised in the city's west end. He was adopted as an infant; his adoptive father was a firefighter. When he was almost one year old, Healey lost his sight due to retinoblastoma, a rare cancer of the eyes. His eyes had to be surgically removed, and he was given ocular prostheses. Healey began playing guitar when he was three, developing his unique style of playing the instrument flat on his lap. At nine years old, his musical talents were showcased in an interview on the TVOntario children's programme Cucumber. When he was 15, Healey formed the band Blue Direction, a four-piece that primarily played bar-band cover tunes and featured bassist Jeremy Littler, drummer Graydon Chapman, and schoolmate Rob Quail on second guitar. The band played at clubs in Toronto, including the Colonial Tavern.