This appears to be a promotional hand out for a show at Jimmie Mad House Of Fun.  Sorry there is an unfortunate racist joke on the back, but this was emblematic of the times.  

From my limited internet research this may have belonged to Ira Orville "Jimmie" Husskisson (1882-1951).  Ira was a vaudeville actor. He operated the Valley Park Hotel after retiring from the stage. The lounge and the Hotel became a gathering spot for Meramec River resort owners.