During the late 1800s, Chauncey Olcott, a tugboat operator with show business aspirations, talks his way into a dinner party for star Lillian Russell. After he sings, Lillian speaks approvingly of his voice, and with that to bolster him, Chauncey Stells his mother, Mrs. Brennan, that he intends to leave home to pursue a singing career. Mrs. Brennan gives Chauncey a watch that belonged to his father, and asks him not to use his father's name until he can honor it with success. Chauncey pawns the watch to buy a banjo and, using the stage name Jack Chancellor, travels around the country singing by the roadside. One day, he trades his carriage and some money to a singing waiter for the lease on a bar in the country. Later, he stops a runaway horse carrying beautiful Rose Donovan and immediately falls in love with her. Chauncey's plans are stymied when he learns the real owner of the bar is Nick Popolis, who demotes Chauncey to janitor, and to make matters worse, Rose is engaged to a man named Terry O'Rourke. Vowing to love Rose from afar, Chauncey joins a minstrel show. Rose brings Popolis, Terry and her father John to New York to hear Chauncey sing in the minstrel show. There, Terry discovers Chauncey's feelings for Rose and sends some of his friends to beat up the singer. After Chauncey wins the fight with the help of his friends, Rose suggests that he meet her and her father at church the next day, but before he gets there, Chauncey is arrested on a warrant sworn out by Terry's friends. Several days later, Duke Muldoon, another member of the minstrel show, pays Chauncey's bail, but by this time, he has lost his job. Searching for a new job, Chauncey again encounters Lillian Russell, and she hires him to sing in her show. Publicity rumors of a romance between Lillian and Chauncey so disturb Rose that she travels to New York to discover the truth. Although Chauncey tries to explain, Rose misunderstands, and hurt, returns home. When Lillian's show closes, Popolis, who manages the Irish singer William Scanlon, hires Chauncey to sing in the show. For the first time, Chauncey performs using his own name. On St. Patrick's Day, Scanlon is unable to sing, and Chauncey takes his place. Although the crowd is furious at first, Chauncey's voice enchants them, and Scanlon dubs Chauncey his successor by giving him a watch he received from the Prince of Wales. Chauncey's mother is so moved by his singing that she apologizes for not being more supportive. Because Donovan, an alderman, only saw Chauncey perform in minstrel makeup and under a pseudonym, he does not recognize him and asks him to sing at a political rally. Chauncey agrees, then asks Rose to elope with him. Duke is delegated to bring Donovan to Greenwich, Connecticut after the ceremony. At first Donovan is furious, but when Chauncey promises to marry Rose again in church, Donovan gives the couple his blessing.