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. A year later, Sexsmith and his family moved to
Toronto, living in an apartment in
the Beaches neighbourhood. Sexsmith recorded and released the full-length cassette ''There's a Way'', which was produced by
Kurt Swinghammer. Between 1997 and 2001, Sexsmith released three more albums, and then
Cobblestone Runway in 2002. On June 16, 2011, Sexsmith 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" and a Canadian Indy Award. The album
Long Player Late Bloomer was shortlisted for the
Polaris Music Prize. Sexsmith's 14th full-length album,
Carousel One, was released in March 2015. In 2017, Sexsmith published his debut novel,
Deer Life, through
Dundurn Press. It was well received and
Publishers Weekly wrote that the "novel has much the same effect as his music, conveying uncertainty with fearlessness and heart." In February 2024, Sexsmith staged a retrospective concert at Toronto's
Massey Hall, his fifth performance at the venue. Sexsmith has collaborated with many artists throughout his career. In 2002, he sang a duet with
Coldplay's
Chris Martin in the song "Gold in Them Hills", which appeared as a bonus track on the album
Cobblestone Runway. He also sang on "An Elephant Insect", which appears on the 2003
Shonen Knife album,
Heavy Songs. In 2005, he released a collection of songs recorded with drummer
Don Kerr during the production of
Retriever, called
Destination Unknown. Also in 2005, Sexsmith sang on the track "Song No. 6" by Norwegian singer-songwriter
Ane Brun, which appeared on her album
A Temporary Dive and again on her
Duets album later the same year. In 2006, he performed a duet of "So Long Marianne" with
Leonard Cohen in
Yorkville, Toronto. In 2014, he wrote and sang a duet together with Dutch singer-songwriter
Marike Jager, titled "Don't you", featured on her album
The Silent Song. Sexsmith's songs have been performed and recorded by a number of well-known musicians, including Elvis Costello,
Feist,
Rod Stewart,
Emmylou Harris, and
Nick Lowe. Sexsmith co-wrote "Brandy Alexander" with Feist—versions appear on his
Exit Strategy of the Soul and on Feist's album
The Reminder. A version of Sexsmith's "Whatever It Takes" appeared on
Michael Bublé's 2009 album,
Crazy Love. In 2004, fellow Canadian singer-songwriter
k.d. lang covered Sexsmith's song "Fallen" on her album
Hymns of the 49th Parallel. In 2010, Sexsmith appeared on "Liberace", a track off the album
Vaudeville by Canadian rapper
D-Sisive. In 2012, his song "Gold in them Hills" was included on
Katie Melua's album
Secret Symphony, and "Right About Now" was covered by
Mari Wilson on the album
Cover Stories. In 2012, Sexsmith appeared on
Lowe Country: The Songs of Nick Lowe, a Nick Lowe tribute album, where he covered Lowe's 1994 song "Where's My Everything?" Sexsmith sang the lead vocals on a song from Ryan Granville-Martin's 2013 album,
Mouthparts and Wings, which features a different vocalist on each track. Sexsmith was featured on vocals on the
Mel Parsons song "Don't Wait", from her 2015 album,
Drylands. In 2023, Sexsmith appeared on the track "Granddad's Song" by Swedish singer-songwriter
Peter Morén's (
Peter Bjorn and John) project SunYears, featured on the debut album,
Come Fetch My Soul! Writing Sexsmith published a book on September 16, 2017, called
Deer Life. It has been described as a "grown up fairy tale" by Sexsmith himself. It is the artist's first effort as an author. ==Personal life==