Riding High (1950 film)

Riding High 1950 is a black and white musical racetrack film featuring Bing Crosby and directed by Frank Capra in which the songs were actually sung as the movie was being filmed instead of the customary lipsynching to previous recordings. The movie is a remake of an earlier Capra film called Broadway Bill 1934. While the film is generally a light musical comedy, it has an unexpected tragic turn in its story.

Doing poorly at work, Dan and his groom Whitey Clarence Muse leave town to enter Bill in the Imperial Derby, but first must find money for the entry fee. He and old pal Professor Pettigrew Raymond Walburn each try to con the other out of a few bucks, then end up singing the Yale school song to get out of a restaurant tab they cant pay.Maggies younger sister Alice Coleen Gray is secretly in love with Dan, so she offers him some money, pawning her belongings. Whitey is beaten up trying to win some in a craps game, and Broadway Bill is carted away because Dan doesnt pay his feed bill. Dan is jailed, too. ........

Source: Wikipedia