In 1993, while still a member of Propagandhi, Samson released a fifteen-track solo album on cassette tape, entitled Slips and Tangles.

Following the critical success of The Weakerthans, Samson's side of the split was re-released online by G7 Welcoming Committee as a digital EP in 2006.

In 2006, he and his wife Christine Fellows recorded The Old House, an album intended as a Christmas gift for friends and family.

Both Samson and Fellows also participated in writing and performing music for Clive Holden's multimedia project Trains of Winnipeg.

[6] He appears on Michael Feuerstack's 2014 album Singer Songer, contributing vocals to the song "Friday Night Guard".

[7] In 2015, Samson, Fellows, Ashley Au and Jason Tait collaborated on the music for For the Turnstiles, a dance performance by Winnipeg's Contemporary Dancers troupe inspired by Neil Young's 1974 album On the Beach.

In 2018, Samson recorded a version of Fellows' "Saturday Night at Utopia Parkway" for a split single with American musician Kevin Devine.

In 2006, Samson championed Miriam Toews' novel A Complicated Kindness in the Canadian Broadcasting Corporation's annual Canada Reads, and the novel went on to win the competition.