Sylvia Bruce, Marion Davies, an infatuated schoolteacher, follows Bill Williams, Bing Crosby, a popular crooner, to Hollywood where he is to make a picture. On board the train she secures a job as maid to Bill's French fiancée and leading lady, Lili Yvonne, Fifi D'Orsay, and meets the film's director, Conroy, Ned Sparks, and promoter, Baker, Stuart Erwin. On arrival in Hollywood she is befriended by Jill, Patsy Kelly, and the two share rooms in the busy studio town.
At the Independent Art Studio, where the film is being made, Lili's temperament and lack of talent cause Conroy considerable concern. After a moment that turns sour when Sylvia, disguised as a fan, pretends to ask for another star’s autograph and a blackfaced insult is tossed, Lili refuses to continue unless Sylvia is removed. She is persuaded to stay, and production continues with her performing “Cinderella's Fella,” but Conroy remains dissatisfied and an angry Lili walks out. Sylvia then impersonates Lili’s rendition of the song and ends with a parody of Lili's tantrums. When Lili returns, there is a brawl in which Lili suffers a black eye. Baker, who has heard about Sylvia, intervenes by firing Lili and offering Sylvia the part.
Baker asks Sylvia to accompany him to a party but withdraws when Bill shows his own interest in her. Bill takes Sylvia to dinner and to the party, but a quarrel erupts and she accuses him of insincerity. Bill deserts the film and goes with Lili to Tijuana, where he drinks heavily and receives a telephone call from the studio with the ultimatum that if he does not return they will hire a replacement. Lili advises him to let them do so and suggests that they fly together to New York and on to Paris. Sylvia finds him and pleads for him to return to the studio but she returns without him.
In Hollywood there is difficulty with the replacement, and eventually Bill reappears at the studio to rejoin Sylvia in the film’s closing sequence to sing Our Big Love Scene.
The film is rich with musical numbers and behind-the-scenes moments. The opening moment features Crosby singing Beautiful Girl before his departure for Hollywood, as technicians work to record it. A grand production number on the train follows, with him and a chorus singing Going Hollywood, and he even offers a snippet of Just an Echo in the Valley. Crosby’s voice is heard again performing Our Big Love Scene on the radio when Jill is showing Sylvia her apartment. A dream-sequence production number, We’ll Make Hay While the Sun Shines, appears with Crosby, Davies, a chorus, and dancers, enhanced by thunderstorm effects. An impersonation act by The Radio Rogues is filmed at the studio and includes imitations of Kate Smith (When The Moon Comes Over The Mountain). The sequence also features impressions of Russ Columbo with You Call It Madness But I Call It Love, Morton Downey with Remember Me?, and Rudy Vallee with My Dime Is Your Dime. Crosby closes the party with After Sundown.
Throughout the film, archive footage appears from other era icons, including Robert Montgomery and Wallace Beery, as well as Norma Shearer and Marie Dressler, weaving a nostalgic thread of Hollywood’s golden age into the main story of Sylvia, Bill, and their tangled romance and ambitions.
