Rum Rebellion began in 2005 as a group of friends who got together to play Irish traditionals and sea shanties for fun. They started playing at Portland Saturday Market and busking outside of bigger shows, mostly so they could get enough money to get into the show and buy some beer. After a bit they decided to start playing punk shows so they added bass and drums. A few big shows with Broken Bones, The Tossers, and the Real McKenzies helped quickly establish them in the Portland music scene. The release of "Cruisin' for a Boozin'" in November 2006 led to their first tour shortly thereafter.