The Skyway is Falling is a two-act comedy about four bungling criminals who set out to rob Chicago’s landmark toll plaza on the Indiana border. Dutch, Sport, Hoss, and Chief have chosen a life of crime out of necessity; that is to say, there is little else they can do successfully, and as the play demonstrates, their collective skill as thieves is at best questionable. Skyway turns the crime noir genre on its side, mixing the "hard-boiled" with slapstick reminiscent of Abbot and Costello and the Three Stooges. In addition to its hard-edged dialogue and comic performances, Skyway has a heart. Each of the central characters is in dire need of a particular human quality to become fully realized. Hoss, Sport, and Dutch must acquire the virtues of courage, intellect, and compassion respectively, while their boss, the elusive Chief, pulls strings behind the scenes to gain their support, as well as conceal his dubious motives for executing this gutsy and dangerous heist.