The story of Red Orkestra is the story of Johnny Charmer.

Canadian singer-songwriter Johnny Charmer burst onto the Toronto music scene in early 2000, having joined Canadian indie darlings Red Autumn Fall as a guitarist and keyboardist. Shortly after the demise of the band, Johnny formed Charmer with ex-RAF singer Simeon Ross, and drummer Gail Thompson, along with Winnipeg ex-pats Steve Payne and Brad Sveistrupp. After several years playing shows across Ontario and Quebec--and even a tour in the Northwest Territories--Johnny left the stalling band to play guitar with Toronto rock ‘n' roll mainstay, and Fading Ways Records chief, Neil Leyton, and eventually to form his own band, Red Orkestra. Red Orkestra started as a side project for Johnny as an outlet for his writing and the original line-up included Leyton on bass, Devin Stoneham on drums, and Ian "Loaf" Woodward (the Pariahs) as lead guitarist. What began as a side project, however, quickly became the focus of Charmer's musical efforts.

In May of 2004, Red Orkestra released their debut album After the Wars to critical acclaim. Embracing the new technologies that were revolutionizing the music industry, Johnny chose to release his album with a Creative Commons license, to enable fans to freely copy and share his music without fear of legal repercussions. It would be the world's first internationally distributed Creative Commons CD release.

Shortly after the release of After the Wars, Johnny's band-mates returned to their own projects, thus leaving the project as a band of one. Having relocated to Waterloo, Ontario, Johnny re-staffed the band with a pool of local musicians including 3 former Candidates: guitarist Stephen Parkinson, bassist Neil McDonald, and drummer Vince Wardell; as well as George Bettencourt (bass/guitars), Rick Andrade (drums), and Paulo Moreira (bass) . Shortly after they were in the studio with producer Steve Payne recording Life with the Machines; the Red Orkestra's second full-length album. Life with the Machines was released in July 2006.

Spring 2007 saw Johnny head to Europe for his first tour on the Continent in support of Life with the Machines. Opening for Neil Leyton (at the time located in London, England), the "Hyperventilating Tour" saw Johnny play solo in 14 German cities in 17 days. On the success of that tour, Johnny returned to Europe in October 2007 (again opening for Leyton) in support of the Red Orkestra EP Enola (George Bettencourt would also make the trip this time). The 15 show tour took them through Italy, Switzerland, the Netherlands, Germany, and Sweden in a mere 18 days. The Enola EP was released in Canada in March 2008.

2009 witnessed the solidification of the Red Orkestra line-up with Stephen Parkinson on guitar/pedal steel and George Bettencourt on bass. The band went into the studio at the beginning of the year to record the pared-down All's Well in Heaven and Hell. The record was released early in 2010. Work has begun on the next full-length record.