Wolfe Brothers Entertainment, originally conceived the idea of a pilot to be called Rags To Rick. Principle shooting started June 2013 in Aurora Ontario Canada at the corporate office of Rick Smiciklas. The show was influenced by personal events in his life. In the first episode he opened his 100th chicken wing franchised restaurant only to tell his franchisees that he would be playing himself in a fictitious mockumentary. Childhood friends Lars, Billy, Franco and Mild Ricky played themselves. None of them had any acting experience. No writers, directors were ever commissioned. After financing difficulties in Nov 2013 the show could no longer be financed by the Wolfe Brothers, they sold the footage to a new entity called Passion Play Media who became the rights holder who rebranded the show to Wingmen. Roy Wolfe stayed on as a consultant however relapsed into drugs and was replaced by his brother Mitch who was eventually cast to play himself as the executive producer. Originally created as a TV show, the show had to be recut to a digital format before it could air on Amazon prime. To date over 8 million dollars has been spent on this 8 hour 30 episode Pilot.