ComedySportz St. Louis was launched as a branch of the Kansas City ComedySportz (the most successful ComedySportz location outside of the home theater in Milwaukee) in 1997. It was helmed on the business side by Clancy Hathaway, owner and manager of the Kansas City CSz. The artistic/performance side was managed by Eric Karwisch, a recent transplant to St. Louis, and long-time performer with the Indianapolis CSz. The original ensemble pulled in many member from groups existing in St. Louis at the time, including the Madding Crowd (Al Keith Richardson, Jammer Bicks, Adam Peck, Michele Jackson), Brand X, and City Improv (Adam Peck, Michele Jackson, Spencer Farris). The Ensemble was homeless for the first several months, practicing at a local technical college, performing at private events, and competing "against" the Kansas City team at remote shows in the Eastern half of Missouri. The opportunity to move in to the old Laugh Tracks/Catch a Rising Star location in historic Union Station developed, but Eric and Clancy were reluctant to try to run the show and bar businesses in a new location. One of the performers, Mike "Painter" Buchanan, agreed to open and run the bar as Sportzmanz Park. ComedySportz, St. Louis opened in Union Station in the fall of 1998. In late 1999, after a shake-up of ComedySportz on the national level, several cities broke away from the national corporate structure. Kansas City, St. Louis, and Green Bay, continued business as usual, but under a new name: ComedyCity.
Buchanan reportedly had difficulty keeping the bar operating at a profit, and had developed artistic differences with the ComedySportz/ComedyCity leadership. He also had the lease to the theater space. In early 2000, he took steps to remove ComedySportz/ComedyCity from the space, and reopened under the CITY Improv. name (the group and school he had belonged to prior to ComedySportz) with several former ComedySportz/ComedyCity performers, including Adam Peck, Michele Jackson, Chris "Pooper," Miguel, Dave and others.