Synopsis

Act One

In 1946, the town of Fair Oaks, Indiana. wakes to greet a new day. It is one of those beautiful summer days, with a magnificently clear blue sky. A solitary figure appears. As he heads for his task, he stops to enjoy the quiet and relish the moment. He begins to sing, and as the town awakens others join him . The song is a hymn to the charms of their time, which they are unaware will soon become a bygone era. (Memories Of  Home)

As Gertie Applebaum works in her kitchen, her son, Jimmy - an energetic and resourceful

young man, readies for work. Before he can rush off, his girlfriend Mary arrives and stops

him at the door. After Jimmy leaves, Gertie and Mary reminisce about how Mary and

Jimmy became a couple. During this, Mary confides in Gertie (When We Were Young).

At the grocer,  Jimmy's boss Vic, reveals his affection for their town, and for Jimmy.

Vic asks Jimmy to become his partner. Jimmy must now confess his ambition to leave

Fair Oaks and seek his fortune elsewhere (I've Got Plans). This causes a stir among the

townsfolk. (Traveling Music). Suddenly Mary arrives. Immediately the crowd disperses,

and Jimmy - who has not yet shared his plans with Mary - is forced to confess everything

to her right then. Jimmy then departs, and Mary is left alone to contemplate her feelings

(When There Is Love).

Days later, Jimmy is packed and about to leave. But he is conflicted about his ambitions, his feelings for Mary, and his own doubts. His mother encourages him to follow his heart, wherever it may lead. Jimmy is beginning to realize the depth of his love for Mary, but remains resolved to leave Fair Oaks (Jimmy's Goodbye).

                                                As Jimmy arrives in Chicago, he is introduced to the many charms of this

                                                vibrant city (Welcome To The Second City). Inside the office his office, Nick D’Angelo                                  and his henchmen are planning some small con when Jimmy interrupts. 

                                                Although Evie Starling, Nick's girlfriend tries to dissuade him, Nick and his

                                                cronies trick Jimmy into joining ther organization (The Thrill Of It All). Upon    

                                                doing  so, Nick, Jimmy and the other gangsters leave.  Evie's girlfriends, both    

                                                hookers as she was once herself, arrive and they discuss the pros and cons of

                                                being a gangster's moll versus streetwalking (Working Girl). Meanwhile, the

                                                gangsters  take Jimmy to see their tailor to get him properly outfitted for his

                                                new role as part of the "association of investment counselors." (Clothes Make

                                                The Man) Jimmy decides to call Mary about his good fortune, but she refuses

                                                to take his call.

Later that evening, Nick takes his gang to dinner. Nick intends this as opportunity to demonstrate how refined a gentleman he is.  But they meet a snooty waiter who lectures the group on proper manners and class distinctions. (We Don't Do That Here!)  After dinner the gangsters return to Nick's office for gambling, unbeknownst to Jimmy, as Nick tells him it's the bi-monthly meeting of the association of investment counselors. While Jimmy acts as an unwilling lookout, Sgt Flannigan notices the unusual activity. Soon a police raid ensures, and the gangsters are captured as the curtain falls. (The Raid).

Act 2

Shortly after being arraigned, Evie posts bail for everyone but Jimmy, who remains in jail alone. Back in Fair Oaks, Mary and Gertie wonder why men are so fickle and can't settle down (Men!). During this, Jimmy calls his mother for assistance. Before he can explain his situation Gertie puts Mary on the phone, but Mary hangs up before Jimmy can solicit his mother's help. Jimmy then reflects on his relationship with Mary, as does she (When Did It Start?).

Meanwhile, outside the police station, Nick and his gangsters conspire

to incriminate Jimmy. Evie convinces Nick to allow her a chance to convince

Jimmy to put-in with the gangsters. Nick, sensing that Evie likes Jimmy,

warns her if it doesn't work then she must help convict Jimmy. Evie then visits

Jimmy in his jail cell, and attempts to seduce him. When Jimmy refuses, Evie is

incensed, and promises to get him back in the upcoming court hearing. When

finally brought to court, Jimmy is unable to contradict the evidence presented

against him. Nick sensing victory, instructs Evie to testify. Instead, she ends

up incriminating Nick and exonerating Jimmy. (Evie's Testimony)

                                          Outside the courtroom, Jimmy and Evie say their goodbyes. He has decided to

                                          return home.  She, in turn, shares her plans to leave as well.

                                          Arriving home, Jimmy is given a hero's welcome for capturing the gangsters.

                                          During this, Mary arrives. In spite of her love for Jimmy, she remains reticent

                                          about reconciliation. Jimmy speaks candidly about his experience, and the

                                          lessons he has learned. By finally admitting to her and to himself that he really

                                          loves her and his hometown, he is able to win her heart back. (Finale).