The Day the Bookies Wept is a 1939 American comedy film directed by Leslie Goodwins and written by Bert Granet and George Jeske.

The film stars Joe Penner, Betty Grable, Richard Lane, Tom Kennedy and Thurston Hall.

[1][2][3] Pooling their resources, New York City taxi drivers–who are tired of losing money at the racetrack–designate Ernie Ambrose to go to Kentucky and buy them a racehorse.

[4] Ernie leaves behind his sweetheart Ina and spends all their money on a horse, relying on advice from a fake "colonel" by buying a nag called Hiccup.

At long odds, she bets $2,000 on the drunken horse to win, which it does, bankrupting bookies all over town.