Sing, You Sinners [1938] (DVD)

Sing, You Sinners is a 1930s comedy starring Bing Crosby as a young gambler whose impulsiveness threatens to land his family in trouble.  Also starring  Fred MacMurray, Donald OConnor and Elizabeth Patterson

The three Beebe brothers are talented singers looking to make their way in the world.

Responsible Dave (Fred MacMurray) wants to work in his garage and marry Martha; but his reckless older brother Joe (Bing Crosby) thinks the only way to success is through gambling, much to his loving mothers despair. Young Mike, in the meantime, idolizes Joe and wants to grow up to be just like him.
Joe moves to California to seek his fortune, promising to send for the family when he makes good. He pins all his hopes on the racehorse hes acquired. But its a bigger gamble than his family realizes