The Gambler (1974)

Charismatic professor and errant gambler James Caan owes his bookie tens of thousands of dollars. The film follows him as he scrambles to get the cash, amidst the disapproval of his girlfriend Lauren Hutton and his family, all while still searching for the thrill of the next big win. Caan works well in the role, but the writing really ups the stakes. I kept waiting for the moment of no return disaster for Caan, but that’s not how gambling works. There are both incredible highs and terrible lows and you don’t know which it’ll be until the card flips or the dice settle, which keeps the gambler craving that unknowable result.