9. Monty Capuletti (Rodney Dangerfield) in Easy Money (1983)

THE LOVABLE SQUARE WHO WINS AT THE GAME OF FUN

Monty Capuletti loves to smoke, drink, and gamble. He borders on being your typical square, but this list needs an everyman! A commoner! A guy who loves to gamble as much as he hates his mother-in-law!

Mony's best friend Nicky Cerone (Joe Pesci) has a tip, it's time to get to the racetrack. Tell me, has Aqueduct ever looked so glorious? That's because the track is actually called Hoover Downs and it was shot at Pompano Park even though they reside in Staten Island. I rather liked the track announcers updates, "Sixty seconds to post time... thirty seconds to post time... two seconds to post time... no more bets." And how about Nicky's line to that gambler that's going to co*k-block you, "What are you doing? Buying a house?"

Who hasn't been stiffed by a jockey? But whatever you do, don't stiff Nicky!

studio: Orion Pictures | Director: James Signorelli