Samson joined bassist John P. Sutton and drummer Jason Tait of Red Fisher, another band from Winnipeg's punk scene,[1] and created The Weakerthans as a vehicle for a more melodic and introspective brand of songwriting than their previous projects.

Another was a line from Ralph Chaplin's union anthem "Solidarity Forever": "What force on earth is weaker than the feeble strength of one?"

[2] The band's debut album, Fallow, was released in 1997 on G7 Welcoming Committee Records, and garnered positive reviews from Canadian music critics.

The album was met with positive reviews[4] from Canadian and international critics for its ambitious combination of punk, rock, folk, country and sonnets.

It also became the band's best-selling record to date, and in September appeared on the !earshot National Top 50 Chart as a result of significant airplay on Canadian radio.

[6] In the same poll, Samson wrote the capsule review for another top ten finisher, The Lowest of the Low's Shakespeare My Butt, which he cited as a major influence on his own music.

[9] In a subsequent interview with Canwest News Service, Samson clarified that the band would be taking some downtime over the summer of 2009 before deciding when to start working on their next album.

[11] At the same time, they also announced that they were recording material with Jim Bryson for his album The Falcon Lake Incident, which was released on October 19, 2010.

[15] The Gimlet Media podcast Heavyweight, launched in 2016, brought fresh attention to the band by selecting "Sun In An Empty Room" from the album Reunion Tour as the show's theme and closing music.