Robertson was born in Scarborough, Ontario. He is the youngest of five children, with two sisters, Lynn and Bonnie, and two brothers, Bill and Doug; He claims to have been named on a bet. His mother, Wilma, was a secretary for Imperial Oil, and his father, Earl, worked both as a shipping foreman for Honeywell, and as an egg grader. He believes that his conception was an "accident" because he is several years younger than his siblings, who were all born about one year apart. He credits this situation with allowing him to have the experience of being both in a big family, and an only child—once his siblings moved out of their home.\n', '

Robertson began working part-time when he was 13 years old. He has bragged about being named employee of the month at his local Wendy\'s in July 1985 (he considers this his life\'s greatest accomplishment). He also answered phones at a CAA office. Robertson appeared in the music video for "All We Are" by Kim Mitchell from Mitchell\'s 1985 album Akimbo Alogo.\n', '

Robertson was brought up in a home where country music was played almost exclusively; he is still fond of it today. He sang harmonies with his family and learned how to play guitar, which his father also played. Once he began playing guitar for other people, around grade five, he knew he wanted to be a performer. He was in several bands during his school days including a band that covered a collection of rock artists, such as Rush and Kim Mitchell.\n', '

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