He has toured with Feist, Final Fantasy, Scott Thompson and has been a guest performer with Wilco, The Wallflowers, Edie Brickell. He was a member of Blue Rodeo from that band's inception, departing the band after their 1992 album Lost Together. He was also a member of The Hidden Cameras and Slutarded.
His first solo album was Bob Wiseman Sings Wrench Tuttle: In Her Dream in 1989. "Wrench Tuttle", the credited songwriter, was in fact simply a pseudonym for Wiseman himself. This record yielded the video "We Got Time", which was a minor hit on Much Music.
His best-known songs include "Have a Nice Day" (from 1993's City of Wood), a harsh attack on controversial Canadian lawyer and Western Canada Concept founder Doug Christie, who often defends racist and neo-Nazi clients, and "What the Astronaut Noticed and Then Suggested" (from 1991's Presented By Lake Michigan Soda), an existential zydeco ditty which was later used as the theme song to the CBC Television series Material World.
Wiseman has also produced recordings for Ron Sexsmith, Bruce McCulloch, The Lollipop People, Katie Crown, Kyp Harness, Bourbon Tabernacle Choir, Eugene Chadbourne, Bob Snider, Edie Brickell, Andrew Cash, Sam Larkin, and The Lowest of the Low.
Since 2000 he has made super 8 films and videos which he accompanies live on accordion, guitar or piano.
Bob Wiseman is a brother to Ron Wiseman, a Jewish Jazz/Reggae singer/songwriter.