It is Chicago in the 1930s, and the closing night of Oscar Jaffee's latest theatrical disaster, a play about Joan of Arc. Producer/director Oscar, has failed to pay his cast for the last two weeks and they are not a very happy crew. Oscar escapes the angry company, leaving a message for his press agent, Owen O'Malley, and business manager, Oliver Webb, to meet him tomorrow on the Twentieth Century, a luxury liner bound for New York.
On the train, Oscar tells his two aides that, in spite of four consecutive failures, he is not ready to be throw in the towel. Oscar then explains to Owen and Oliver the reason for the trip and for his insistence on obtaining Drawing Room A: none other than Lily Garland will be boarding the train at Englewood and taking up occupancy in Drawing Room B. Lily, once lowly accompanist Mildred Plotka from the Bronx, had been discovered by Oscar four years ago. He had transformed her into a star of the theatre, and becoming lovers in the process. But the temperaments of the pair made the relationship volatile and ultimately impossible. Lily left Oscar and the theatre behind and became a movie star who wins Oscars - without the surname of Jaffee. Oscar is hoping to lure Lily back to him and sign her to a contract. In a flashback, we see how Oscar made nobody Mildred Plotka into star Lily Garland.
Oscar is approached by the conductor, who is also just happens to be a playwright, then Lily boards the train. She bids an excessively dramatic farewell to the dashing Bruce Granit, her current co-star and lover. He has seized on Lily as his meal ticket. Lily is dismayed when Bruce reappears, having decided not to leave her alone on the trip after all. Oliver and Owen present themselves to Lily and tell her that Oscar needs her desperately. Lily's response: she'd rather die than go back to Oscar. In another flashback, we see Lily and Oscar in happier times, when they were everything to each other.
In the observation car, we meet another passenger, Mrs. Letitia Primrose. Mrs. Primrose, the founder and president of Primrose Restoria Pills, claims to be a pious doer of good works. In reality she is an insane religious fanatic, recently escaped from an asylum and also a passer of phoney cheques. In addition, she is the one responsible for putting up stickers all over the train that read, "Repent for the time is at hand." Alone, Mrs. Primrose sings out her credo.
Inspired by the stickers, Oscar decides to tempt Lily back with the promise to star her in The Passion of Mary Magdalen. In their separate suites, Oscar and Bruce, former and current flame of Lily, admit to themselves their need for Lily. Each resolves to keep Lily to himself.
Oscar finally confronts Lily in person. She describes the wonders of her new life as a Hollywood goddess, while Oscar accuses her of selling out to the world of celluloid. Meanwhile, Oliver encounters Mrs. Primrose who, as part of her religious mission, offers to provide the financing for Oscar's Magdalen play. If Lily has given Oscar the brush off, his fortunes seem to be rising
Four porters appear in front of the curtain to offer their philosophy of life. Mrs. Primrose presents Oscar with a cheque for $200,000 who shows the cheque to Lily and tells her his plan; Lily is carried away by the idea of playing the woman who "has kept the whole world weeping for centuries." As Lily ponders signing Oscar's contract, she and the other five principal characters voice their sentiments. Lily weakens when Mrs. Primrose offers to finance a Magdalen movie in addition to the stage play. But Oliver, Owen, Oscar and Lily soon are horrified to learn the truth about Mrs. Primrose. Oscar sees his dreams slipping down the drain, while Lily is furious that Oscar has made a fool of her. Max Jacobs, a successful Broadway producer (who was once Oscar's office boy), arrives. Max also has a play for Lily, a vehicle written by Somerset Maugham, but Lily is drawn to the role of Mary Magdalen. Alone, Lily ponders her options, finally deciding to accept Max's offer.
Oscar has decided to end it all and distributes his worldly possessions to the loyal Owen and Oliver. Mrs. Primrose attempts to take a gun from Oscar's hand, and it goes off. Oscar emerges unscathed but decides to take advantage of the situation. Pretending to be near death, Oscar asks to see Lily once more and, as his "last request," asks her to sign his contract. Lily signs, but, when Oscar reveals that he is very much alive, Lily reveals that she signed the contract as one "Peter Rabbit." Clearly made for each other, Lily and Oscar embrace.
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