Sexsmith was seventeen when he started playing at a bar, the Lion's Tavern, in his hometown. He gained a reputation as "The One-Man Jukebox" for his aptitude in playing requests. However, he gradually began to include original songs and more obscure music, which his audience did not favour. He decided to start writing songs after the birth of his first child in 1985. That same year, still living in St. Catharines, he collaborated on recording and releasing a cassette, "Out of the Duff", with a singer-songwriter friend named Claudio. Side one of the cassette contained five songs written and performed by Sexsmith; side two featured Claudio.