Wonderful Town is based on a series of short stories by Ruth McKenney.
- Rosalind Russell - Ruth Sherwood
- Edith Adams - Eileen Sherwood
- Cris Alexander - Frank Lippencott
- Jordan Bentley - Wreck
- Dort Clark - Chick Clark
- George Gaynes - Robert Baker
- Warren Galjour - Tour Guide/Associate Editor/Greenwich Villager/Policeman
- Dody Goodman - Violet/Greenwich Villager
- David Lober - First Cadet/Greenwich Villager
During the summer of 1935 in Greenwich Village, New York, a tour guide leads a group of sightseers on a tour of Christopher Street and its colorful residents.
When the tourists have departed, the witty Ruth Sherwood arrives in Greenwich Village with Eileen, her younger sister. The two have just arrived from Columbus, determined to forge a life in the big city as a writer (Ruth) and an actress (Eileen). Soon they are living in a basement apartment, recently vacated by Violet, loaned by the landlord, Mr. Appopolous. Their apartment building is shaken frequently by dynamite from the construction of a subway underneath them as well as Violet's returning customers. The sisters are soon stricken with homesickness for Ohio.
The next morning, Ruth and Eileen set out to try their hand at conquering New York, only to find defeat and humiliation. Eileen, at least, has gotten food from a food samples man, as well as Mr. Valenti, but has also met Frank Lippencott, a local Walgreens manager who has developed a crush on her. Ruth, however, is left to wonder at her sister's magnetic appeal and her own unique romantic abilities — a talent for repelling men so successful that she could write a book entitled "One Hundred Easy Ways to Lose a Man."
Eventually, Ruth talks her way into the offices of a short story magazine, where she meets Bob Baker. Bob likes Ruth, but advises her that she has little chance of success, and tells her flat out what a waste of money and time it was to come to New York, because he along with many others have done the same thing. Undaunted, Ruth leaves three stories with Bob in the hope that he will read them.
Meanwhile, Eileen has been eating all of her lunches free at Walgreens, and finds herself infatuated with Frank, and invites him over to dinner so Ruth can have free lunches when she goes to Walgreens, too. Bob arrives at the apartment, looking for Ruth, and Eileen invites him over for dinner as well. The phone rings, and it is Chick Clark, a newspaper editor, whom Eileen met in an elevator, wanting to see Eileen.
The upstairs neighbors, Wreck, an out-of-season American football player, and his live-in lover, Helen, ask the girls to hide Wreck while Helen's mother, Mrs. Ella Wade is in town, because Mrs. Wade does not yet know about Wreck. Eileen happily agrees to stow him in their apartment, much to Ruth's hesitation. Wreck describes his lucky history as a student at Trenton Tech, who got by very well only because of his ability with football.
Eileen has invited Frank Lippencott, Bob Baker, and Chick Clark, a slimy newspaper scribe whom she has met with the object of furthering Ruth's career, over for potluck supper. Unaware of each other's feelings, both women find themselves attracted to Bob. Soon, all five of them are seated around the cramped apartment trying to fill the awkward silence. Meanwhile, Helen deals with her overbearing and exaggerated mother.
Ruth and Bob talk over the quality of her stories, and he advises her to write about what she knows rather than flights of fancy. Both say several wrong things, and he finally tells her off. He soon regrets it as Ruth rushes inside in tears.
While all this is happening, anxious to be alone with Eileen, Chick Clark creates a bogus assignment for Ruth. He sends her off to the Brooklyn Navy Yard to interview a group of Brazilian navy cadets. She quickly realizes that their sole interest is to learn and dance the Conga. The sailors follow Ruth home, where the girls soon find themselves in chaotic confusion, as all the citizens of Christopher Street join the conga line in a finale. Ruth runs into Bob and gives him a piece of her mind, while Eileen is hauled off to jail for causing the riot.
In the local jail Eileen finds herself practically running the place, with Officer Lonigan and his brigade of doting Irish police officers at her beck and call. Given her name, they are convinced that she is Irish, and they serenade her and are not the least discouraged when she says she is not Irish. Ruth comes to assure her that she will bail her out as soon as she collects the money from her new job as a promoter for the Village Vortex, a local nightclub. At the club, Ruth digs the rhythm of swing. Meanwhile, Wreck is awkwardly masquerading as a wealthy art collector to meet the approval of Helen's mother, and Chick is frantically calling Eileen, trying to make things right.
Thanks to Bob, Eileen is soon released from jail, and the sisters learn that Appopolous has been so scandalized by a missing picture that he painted (that was actually stolen and sold for $2 by Helen and Wreck for Wreck to stay at the Y) as well as Eileen's arrest that he has threatened to evict them. Eileen discovers that Ruth is also attracted to Bob Baker, and the two of them wish, for a moment, that they had never left home. Eileen is then confronted by the rhythmical Speedy Valenti, owner of the Village Vortex (the night club), who makes her New York debut as a singer because her fame has reached the front page of the news. Appopolous immediately changes his tune now that one of his tenants has a paying job, and extends their lease.
Eileen soon learns that Bob Baker has quit his job as a result of a disagreement with his boss about Ruth's story on the Brazilian sailors. Eileen is thrilled that Bob quit his job and assures the unbelieving Bob that it's love that he feels for Ruth. Bob, faced with the facts, hesitantly realizes the truth that it is love.
The mood at the Vortex turns jazzy. Eileen finds herself with a case of stage fright and she convinces Ruth to join her on stage to sing. Chick arrives to make amends and presents Ruth with a press pass: His boss has read her story about the Brazilian sailors and loved it, and given Ruth a job to take on the following Monday. The Vortex is alive with singing and dancing, and Bob decides it is the perfect moment to let Ruth know how he feels. The curtain closes as Eileen and the guests at the club sing "It's Love" along with everyone in a finale in celebration of Ruth's and Bob's new found affection.
- Act I
- "Christopher Street" — Tour Guide and The Villagers
- "Ohio" — Ruth Sherwood and Eileen Sherwood
- "Conquering New York" — Ruth, Eileen, First Cadet, Violet and The Villagers
- "One Hundred Easy Ways" — Ruth
- "What a Waste" — Robert Baker and Associate Editors
- "A Little Bit in Love" — Eileen
- "Pass the Football" — Wreck and The Villagers
- "Conversation Piece" — Ruth, Eileen, Frank Lippencott, Robert and Chick Clark
- "A Quiet Girl" — Robert
- "Conga" — Ruth
- Act II
- "My Darlin' Eileen" — Eileen, Drunk and Policeman
- "Swing" — Ruth and Villagers
- "Ohio" (Reprise) — Ruth and Eileen
- "It's Love" — Robert and The Villagers
- "Wrong Note Rag" — Ruth, Eileen and The Villagers
- "It's Love" (Reprise) - Full Company