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 Follie di Broadway 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.
Former "Our Gang" cast member, Eugene Jackson, plays the stable boy Just Garland questions. He appeared as "Pineapple" in the popular film series. In addition to a long career as a character actor, he was an accomplished dancer who also instructed aspiring future dancers in his later years.