Hard to Get

Hard to Get with Dick Powell and Olivia de Havilland.  Maggie Richards (Olivia de Havilland) is the daughter of a wealthy Park Avenue family.  In a pique she declares that she will not be accompanying the family to their summer house in Newport and takes off for a spur of the moment drive.  On a country road, she finds herself in need of gas and stops at an auto court managed by Bill Davis (Dick Powell).  She is outraged to learn that the $3.48 (fourteen gallons of gas and a quart of oil) she owes cannot just be "charged" to her father.  Bill insists that she work off her debt by cleaning the ten cabins of the motor lodge.  She does so, but not willingly, and she vows to get revenge for this humiliation.  She returns the following day full of apologies and woos Bill, setting up a dinner date. She pretends to be a maid in her Park Avenue house and learns that Bill is an aspiring architect with a business idea.  With this knowledge she sets him up for a series of humiliating business pitches to her father, Ben Richards (Charles Willinger), and his friend and competitor, John Atwater (Thurston Hall).  To everyone's surprise and despite getting the bum's rush over and over, Bill never ever EVER gives up. Until, that is, he learns that he is the target of a joke and washes his hands of the lot of them.  Then Ben Richards and Atwater cannot rest until they get a piece of Bill's business plan, and Ben must patch up Bill and Maggie's romance as well.

Dick Powell and Olivia de Havilland

Dick Powell sings "You Must Have Been a Beautiful Baby" and later dresses in blackface and does a Jolson impersonation.

Familiar faces:
Penny Singleton (from the Blondie movies) as Maggie's personal maid
Melville Cooper (Sheriff of Nottingham from The Adventures of Robin Hood) as Mr. Richards' valet
Tom Fadden* (the toll keeper from It's a Wonderful Life) as a gas station attendant
Looks like I was wrong about this one.  It was Irving Bacon.

 *IMDb doesn't even list this one!