Whether revealing the dark underbelly of the casino lifestyle, or tales of strategic card counting, the best casino movies of all time are all imbibed with the. Casino is a American epic crime drama film directed by Martin Scorsese and starring . Guys Choice , Guy Movie Hall of Fame, Casino, Won Based on : Casino; by Nicholas Pileggi. The are a few of the best casino and gambling movies. I chose for #5 21 (), # 4 The Cincinnati Kid (. They make their way around the city in order to find their friend before his wedding. Kirsten Dunst plays a young woman Liddawho is searching for her father James Caan. George ClooneyBrad PittMatt DamonMichael Mantell. Kenny Rogers as The Gambler, Part III: Jeanne MoreauClaude MannPaul GuersHenri Nassiet.