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He was a working-class, down-to-earth troubadour and arguably the most patriotic songwriter that Canada has ever produced. Tom Connors experienced a difficult childhood, marked by poverty, homelessness, hunger, and the challenges of the child welfare system. In his early years, he and his mother begged on the streets of New Brunswick, and when she was jailed, young Tom was incarcerated with her.

Eventually, he was placed in an orphanage and foster care before being adopted by the Aylward family in Skinners Pond, Prince Edward Island. The country music of Wilf Carter and Hank Snow had a profound influence on him and his music. He left his adopted home at age 15 and hitchhiked across Canada, working various jobs for 13 years and occasionally spending a night in jail for vagrancy.

This period, during which he saw much of the country and experienced the seamy side of life, informed his musical persona as a sincere, grassroots songwriter. He was also heard locally on CKGB radio. Lacking amplification at the Maple Leaf and other bars where he performed in Ontario, Connors pounded the floor with his booted foot to establish the rhythm of his songs partly sung and partly recited above the noise of the crowd.

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To avoid damaging the stages, he would place a sheet of plywood under his boot. Connors sang with a piercing edge that reflected the grittiness of life on the road and his hard-won life experience. In , he moved to Toronto and began recording for Dominion.