Strike Up the Band (1940)

Teenage drummer Jimmy Connors (Mickey Rooney) dreams of winning the contest for school bands hosted by popular band leader Paul Whiteman (himself). In order to enter, Jimmy and his pals, including charming vocalist Mary Holden (Judy Garland), must accumulate $200 for the train ride to Chicago, where the contest will be held. Jimmy and his friends decide to put on an epic student play to raise the funds they need, but a sudden illness threatens to cost the band their chance.