In 2004, LA based actor Bob Rusch decided to produce and act in a play called JERRY and TOM, by Rick Cleveland. He told his two producer friends, Dan Parr and Mike Greene, about the show and they both agreed to chip in and do some Theatre for the first time. Fate intervened as Bob found out his roommate Eric Johnson was in the first ever production of the show at the University of Iowa and had long wanted to do it again. Bob then found out that another friend, Dennis Cockrum, was in an early workshop of the play.

Bob quickly cast them both, and Dennis asked his friend Dave Florek to direct. During rehearsal, Bob was trying to find a name for his new theatre company. He told Eric that he wanted every show they do to have a great moment, just like in a play they had both done in Chicago, THE BOYS OF THE PEGGY AUGUST CLUB. That show was about a bachelor party and in one scene, a bunch of high school buddies sang along with their favorite song: ”Skypilot” by the Animals. Eric suggested this for a name and SkyPilot Theatre Company was born. JERRY and TOM was a critical success. A year and a half later, Bob decided he really wanted to make SkyPilot a true ensemble Company. He began to ask a few of his friends from different walks of life to join, with the idea of keeping it small.

They then produced SEXUAL PERVERSITY IN CHICAGO by David Mamet in the spring of 2006. It was again a critical success and, this time, people came and saw it. SkyPilot ended 2006, and their "Chicago Trilogy", with HELLCAB by Will Kern. This was the company's first big audience success, with frequent sold-out houses. It was also a favorite of the critics, with the Tolucan Times calling it "a rollicking ride" and Backstage gushing that "Hellcab is a slice of heaven for the audience. You know you’re watching a good show when you don’t notice the clock. And this is one great show." 2007 started with the world premier of ROCKET MEN by Clyde Hayes, followed with REQUIEM FOR A HEAVYWEIGHT by Rod Sterling and TAKING SIDES by Ronald Harwood.