Flying Fifty-Five (1939)

Bill Urquhart, a young wastrel disinherited by his father, tries to get a job as a jockey – just about the only thing he’s really good at. His name and position work against him, however, so he adopts an alias and prevails upon the charity of a drunken friend Charles Barrington, through whom he meets Stella Barrington - who has not only inherited her father’s racing stables but also his debts. Still incognito, he takes on the job of stable lad for Stella but little does she realise that he could be the man to finally put an end to her money worries forever.

Unfortunately the movie Flying Fifty-Five is not yet available on HBO Max.