Easy to Make Money (1919)

Jimmy Slocum, whose wealthy father continually pays his speeding fines and loses bets to him, wins a $1,000 bet with his father that Katherine Fowler, whom his father wants him to marry, does not love him. Jimmy then wins a $25,000 bet that he can keep from being arrested more than once in the coming year by getting a 12-month jail sentence for fighting in a bar, then sassing the judge.