This musical is based on four short stories by Damon Runyon. In one tale, gambler Feet Samuels sells his body to science just as he realizes that Hortense loves him and that he would rather live than die. In another story, Harriet's parrot is killed, and she has problems dealing with her loss. Then, there is a gambler, "Regret", who has bloodhounds on his trail when he becomes a murder suspect. Finally, "The Brain" is bleeding profusely, and his friends search for a way to save his life through a blood transfusion.
Sixteen-year-old Michael Dunn arrives at St. Basil's Catholic Boys School in Brooklyn circa 1965. There, he befriends all of the misfits in his class as they collide with the repressive faculty and discover the opposite sex as they come of age.
Though visibly frail and weary, President Franklin D. Roosevelt runs for a precedent-setting fourth term. He also oversees plans for the D-Day Invasion and engages in tempestuous summit meetings with his wartime allies Stalin and Churchill.