A musical movie star, who is past his prime, tries to make a comeback on Broadway with a couple of writers, a dramatic director, and a beautiful ballerina.
Tony Hunter (Fred Astaire) has not made a picture for three years and arrives on a train in New York. He sees Ava Gardner and sings “By Myself.” His friends Lester Marton (Oscar Levant) and Lily Marton (Nanette Fabray) greet him with supporting signs. The couple takes a taxi, and Tony in the 42nd Street arcade sings “A Shine on Your Shoes” and dances.
Jeff Cordova (Jack Buchanan) plays the tragic Oedipus on stage. Afterward he tells Tony, Lester, and Lily that he will direct a musical. Lily describes the story as a writer who is tempted by the devil. Jeff sees it as Faust and sings “That’s Entertainment” with the other three. Jeff asks Paul Byrd (James Mitchell) to do the choreography so that he can get the dancer Gabrielle Gerard (Cyd Charisse). She performs in a ballet, and Tony wonders if she is too tall. Paul assures Gabrielle that Tony wants her. She and Tony meet on the stairs and quarrel. Jeff brings Gabrielle and Tony in to meet the investors.
At rehearsal Jeff tells the cast that they will work. Jeff takes Tony aside and tells him to be more assertive. Jeff changes the beginning, and frustrated Tony gets angry, makes a speech, and walks out. Lester makes Lily scream. Gabrielle calls on angry Tony and cries. Tony says they are the ones who matter. He takes her on a carriage ride at night to a park, where they dance.
The show has three days to get ready, and there is too much scenery. Tony and Gabrielle rehearse amid smoke. On opening night out of town Jeff gives the cast a pep talk, but the show lays an egg. Only Tony is at the catered party, but he finds the cast in a room drinking beer. Lester plays piano, and Tony sings “I Love Louisa.” Lester and Tony decide to put on a show, and Jeff says that Tony can do it. Paul tells Gabrielle that he is out, but she won’t leave with him.
The show goes on the road. Gabrielle sings “New Sun in the Sky.” Tony and Jeff sing and dance. Lily sings “Louisiana Hayride.” On the train Tony sees Gabrielle writing to Paul. Lester questions Tony, who admits he loves Gabrielle. Tony, Lily, and Jeff as babies sings “Triplets.”
The show opens in New York. Tony narrates and dances in “Girl Hunt,” a stylized murder story. Hal Benton (Robert Gist) brings a message to Tony in his dressing room and then leaves. Tony sings “By Myself.” On stage Gabrielle and the company thank Tony. He kisses her. They all sing “That’s Entertainment.”
This musical reflects the career situation of Astaire, the writers Betty Comden and Adolph Green, and the producer Jose Ferrer. Hollywood prefers easy entertainment to the more challenging classics such as Oedipus and Faust, which are satirized as being ponderous.