Childhood friends since elementary school, Woods and Walker formed their first band, The Playing Cards, in grade 8.[3] In that form, they played at least one show in Winnipeg as an opening act for Great Lake Swimmers,[3] and were later active as supporting musicians for singer-songwriter Greg MacPherson before reforming as Cannon Bros. They released their debut EP in 2010.[4]
In 2011, the Cannon Bros released an album, Firecracker/Cloudglow.[5] The album appeared on the !earshot National Top 50 Albums chart in January 2012.[6]
They followed up with the album Dream City in 2015.[7] This album also received significant airplay on campus and community radio, and appeared on the !earshot National Top 50 Chart in December that year.[8] The band continued performing in Winnipeg in 2016.[9]