The creators actually had a radio show called 'We Is Radio' in college at UT Austin and got kicked off the air, thus sparking their idea for 'The Wingmen.'
Before making the show, the creators hosted an "alter-ego party" as their casting audition. Actors came to the party and had to create and stay in character while improvising for the duration of the evening. Both Marshall Rimmer and Michael Champion were cast at the party.
The creators/cast members create a loose outline of each episode, though mostly all of the dialogue and character interaction is improvised.
Jordan Crowder's character was originally supposed to be played by Seth Rogen. When Rogen turned down the role, the next obvious choice was to cast another curly-haired Canadian Jew.