This film, the first of 10 to feature both Judy Garland and Mickey Rooney, is also the only one in which she is billed ahead of him. It was also the first film in which she received top billing.
MGM's top juvenile actor of 1937, Freddie Bartholomew, had been announced to play Roger Calverton, but Freddie's Aunt Cissy (who also was his adopted mother) withdrew him before production started because of a contract dispute. In later years, Judy Garland would quip that Freddie really opted out because his voice was changing.
This is the second time Sophie Tucker co-starred with Judy Garland. In Broadway Melody of 1938 (1937), Tucker had played Judy's mother.
Legendary song stylist of vaudeville, Broadway and records, Sophie Tucker was left without a number to belt in this film.
In a scene where Mickey Roonie and Judy Garland are talking about Mickey's life, Judy says to Mickey, "You don't want to wait around until someone drops a house on you!" Flashbacks from The Wizard of Oz!