Sing You Sinners

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.