Technically from 1937 but not released in the US until 1938, this movie stars Vivien Leigh and Rex Harrison. In a small town in Scotland, Vivien Leigh is the daughter of the Provost (basically the mayor) who has higher political aspirations.  Rex Harrison is an English newspaper reporter recently arrived to work at the local paper. Given an assignment to conduct a softball interview of the Provost, he instead publishes a rebuke of the Provost's treatment of a working-class woman who refused to pay her dog license fee.  All hell breaks loose. Rex Harrison is just as entertainingly smug here as he is with his Henry Higgins.

It just shows to go you that I can still be surprised. I had never even heard of this movie that stars Bing Crosby, Fred MacMurray, and a 12-year-old Donald O'Connor. So far this is the only 1938 movie I've run across with even one of these three actors. This is a musical and not only does Fred MacMurray sing, he sings in drag to a Hoagy Carmichael tune.

Three brothers live with their mother but only staid David (Fred MacMurray) has a job to support them all. David wants to marry his sweetheart but won't propose until layabout Joe (Bing Crosby) gets a job so that Joe can support the family when David moves out. Joe doesn't want a steady job but instead hopes to get rich by "swapping" things. Joe eventually moves to California where a lucky series of racetrack bet swaps gives him a sizable stake, which he eventually converts to ownership of a racehorse. Everyone's fortune depends on the outcome of a single race. After much Sturm und Drang he eventually comes out on top, but then (reluctantly) agrees to a steady gig of nightclub singing with his brothers for future income.