The Day the Bookies Wept (1939)

The taxi drivers of the Colonel Cab Company are tired of losing money at the racetrack. When Ramsey Firpo sees the winnings taken home by one of the horse owners, he convinces the other drivers to chip in some money to buy a horse of their own. Firpo taps fellow driver Ernest Ambrose, his sister Ina's goofy boyfriend, to go to Kentucky to buy the horse and, based on Ambrose's success with pigeons, to become the horse's trainer. Despite Ina's warnings to stay away from horse racing, Ambrose goes to Kentucky and meets Colonel March (a con man) and Patsy (his accomplice, posing as his daughter "Gwendolyn"). Colonel March buys Hiccup, a broken-down nag with an alcohol problem, for twenty bucks and makes sure Ambrose pays five hundred dollars for him the next day at the auction. Firpo and the cab drivers are excited to see Hiccup in action (chasing a beer truck down the streets of New York), but Hiccup's performance on the racetrack is disappointing. That is, until Ina overhears Colonel March mention that Hiccup is unbeatable once he's had a few drinks.