Sexsmith has collaborated with many artists. 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". Sexsmith 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, the song "Don't you", featured on her album "The Silent Song".