Mister Cory (1957)

Cory, an ambitious Chicago slum kid with a knack for gambling, gets a busboy job at a posh Wisconsin resort...where his real purpose is to gamble with the staff and guests and romance rich young ladies. Setbacks follow, but Cory eventually rises to a high position in the world of professional gambling. But he just can't forget the glamorous Vollard sisters. And now he has even farther to fall...