Sexsmith was seventeen when he started playing at a bar, the Lion's Tavern, in his hometown. He would gain a reputation as "The One-Man Jukebox" for his aptitude for playing requests. However, four to five years of this led him to play original songs and more obscure music his audience did not favour. He decided to start writing songs after the birth of his first child, Christopher, 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 5 songs written and performed by Sexsmith; side two featured Claudio.
A year later, Sexsmith and his family moved to Toronto, living in an apartment on Woodbine Avenue in The Beaches neighbourhood. Still in 1986, Sexsmith recorded and released the full-length cassette There’s a Way, which was produced by Kurt Swinghammer. Meanwhile, he worked as a courier, and befriended Bob Wiseman whom he met at an open stage. They became friends, and Wiseman agreed to produce and arrange Sexsmith's next release in between his tours with the band Blue Rodeo. Because of Wiseman's busy schedule, work on the album stretched out over several years, overlapping the birth of Sexsmith's second child, Evelyne, in 1989.
Grand Opera Lane finally appeared in 1991, after every Canadian label who Wiseman took it to rejected it. As a result, the album was released independently. Grand Opera Lane was credited to "Ron Sexsmith and the Uncool", utilizing Ron's backing band of Don Kerr and Steve Charles, and also featuring Wiseman regulars Sarah McElcheran (horn arrangements) and Kim Ratcliffe on electric guitar. Eventually on the strength of this album, and the attention garnered by the song "Speaking with the Angel", Sexsmith earned a contract which led to his self-titled album in 1995. The album received wider attention when it was praised by Elvis Costello, for whom Sexsmith later opened.
Between 1997 and 2001, Sexsmith released three more albums before the acclaimed Cobblestone Runway in 2002. Retriever, his next album, is a more pop-oriented album and is dedicated to Elliott Smith and Johnny Cash. In 2004, he performed at the RuhrTriennale in the concert series Century of Song hosted by Grammy Award-winner Bill Frisell. On 1 May 2001, Sexsmith performed "Just My Heart Talkin'" on the BBC's Later... with Jools Holland musical showcase, alongside R.E.M., Orbital, India.Arie, and Clearlake. Holland backed him on piano. It was his second appearance on the show. He continued to grow in popularity, and began to have some radio success, particularly on Canadian adult oriented radio. In 2002, Sexsmith recorded a cover version of "This Is Where I Belong", the title track for a tribute album called This Is Where I Belong - The Songs of Ray Davies and the Kinks, and including contributions from Damon Albarn, Bebel Gilberto and Queens of the Stone Age, among others. About this recording, Ray Davies later wrote, "he has a great voice". On 16 June 2011 Ron and his band performed the Kinks' song "Misfits" with Ray Davies at the Meltdown Festival in London, England. The same year, he won a songwriter of the year Juno Award for "Whatever it Takes". Sexsmith's most recent album is Forever Endeavour, released February 2013.
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