In the early 1930s, aspiring singer Bing Crosby and his Hoboken, New Jersey friends become lost in the Southwestern desert while driving their "flivver" to Hollywood. Although the wayward group ends up back in Hoboken, a determined Bing quickly returns to the road and is taken in by a friendly Indian tribe. When he croons a romantic tune for a bevvy of admiring Indian women, however, Bing is shot at by a group of jealous Indian men. Bing flees the Indians' camp, jumps into his car and crashes into a bus carrying his Hoboken friends. Bing finally arrives in Hollywood, but because of a housing shortage there, is forced to build his own home. To make ends meet, Bing becomes a washing machine salesman. Later, Bing, now a plumber, discovers that his hometown sweetheart, Betty Brooks, and her disapproving mother have left home for Hollywood. Bing follows Betty to Hollywood and spots her performing with matinee idol Reginald Duncan on a movie set. While spying on Betty, Bing accidentally is squirted with black paint and decides to pose as a black bit player in order to get close to Betty. After Reginald tries to convince Betty to forget Bing, Bing begins to sing a love song on the set, and after Betty finally recognizes him, they run off together. Both Betty's mother and a performing lion chase Bing, but Bing and Betty escape in his car, and Betty's mother ends up in a cab with the roaring lion. Later, at a Los Angeles train station, Bing, now a successful radio singer, becomes romantically interested in another young woman after he mistakes her for his sister and kisses her. Bing is immediately accosted by the girl's jealous fiancé, a middle-aged marquis, and flees with his friend Jerry when a police officer begins to chase him. Determined to reunite with the girl, who is unaware of his identity, Bing follows her to a hotel. There he mistakes a married woman for the girl and is threatened by the woman's hefty husband. To find out in which room the girl is staying, Bing and Jerry dress up as tour guides and begin knocking on every door in the hotel. After much confusion, Bing finally locates the girl, but is unable to convince her mother that he is Bing Crosby and not a tour guide. The girl, however, is attracted to Bing and sneaks out of her room and into Bing's friend George Dobbs's room. When George's jealous wife suddenly returns, George hides the girl in his closet. Bing then shows up and sings his latest hit tune, convincing the girl of his identity. The girl springs out of the closet and embraces Bing, then telephones the marquis to tell him that the engagement is off. The enraged marquis races to Bing's room, but Bing and the girl flee down the fire escape together. The misunderstood couple is then pursued by police.