The earnest work of boyish Canadian singer/songwriter Ron Sexsmith won acclaim not from only critics but from fellow performers like Paul McCartney, Elvis Costello, and John Hiatt -- some of the same artists, ironically enough, who initially inspired Sexsmith himself to become a musician. Born in 1964 and raised in the Niagara Falls area, he started his first band at the age of 14, and within a few years earned his first regular gig at an area club. Influenced by Pete Seeger, he began making the rounds on the folk circuit, but soon decided to focus his attentions on becoming a songwriter.
After moving to the Toronto area, Sexsmith formed the Uncool and began issuing his own material in 1985 with the cassette Out of the Duff, followed a year later by There's a Way. He continued performing while maintaining a day job as a courier but did not release anything more until 1991's Grand Opera Lane, recorded by Blue Rodeo's Bob Wiseman. The collection of songs helped earn Sexsmith a songwriting contract, and eventually a recording deal with Interscope Records; teamed with producer Mitchell Froom, he released his self-titled debut in 1995. A follow-up, Other Songs, appeared two years later. In 1999, Sexsmith returned with Whereabouts, again produced by Froom. Three years later, Sexsmith inked a deal with Nettwerk and released Cobblestone Runway in October 2002.