While going to college and working in a speakeasy, Indy meets up jazz great Sidney Bechet who teaches him how to play the blues. Unfortunately, Indy also crosses paths with Al Capone and it's only with the assistance of his dorm roommate, Eliot Ness, that Indy is able to solve a vicious murder and prevent himself from ending up dead.

In New York City, Indy stretches himself thin when he stage-manages a Broadway musical, dates three beautiful women, attends high society parties, reads poetry with Greenwich Village bohemians and trades barbs with the literary wits of the Algonquin Round Table, all accompanied by composer George Gershwin.