Love on a Bet (1936)

In order to raise money to produce a play (as well as prove that the plot isn't ridiculous), Michael McCreigh makes a bet with his Uncle Carlton that he can begin in Central Park in his underwear and, without paying or borrowing for transportation, get to California in 10 days with a decent suit, $100...and a fiance. If he wins, he gets $15,000 to produce the play; if he loses, he must accept a job in his uncle's packing plant.