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Frank Costello
Played by Jack Nicholson in The Departed (2006)   

An Irish gangster in a Boston neighborhood, Frank Costello does not take the threats of the crime world seriously, taking it one day at a time with his wise-ass remarks. Frank invests in a young Collin Sullivan and eventually hires him as his mole in the force, the very reason why he’s more comfortable now than he’s ever been. At 70 years old, he is also quite the ladies’ man.

Senior Swag Line: “I don't wanna be a product of my environment. I want my environment to be a product of me.”



Jimmy Conway
Played by Robert De Niro in Goodfellas (1990)

Based on real-life gangster Jimmy Burke, Conway is the prototype mobster: short-tempered, cocky, sleek-haired, and a thick accent. Jimmy is best buds with fellow mobster Tommy DeVito and new recruit Henry Hill, and together makes more money than they’ve ever had their whole lives. This Irishman is also untouchable – he’s the only guy in the movie who didn’t get “whacked”.

Senior Swag Line: “I'm not mad, I'm proud of you. You took your first pinch like a man and you learn two great things in your life. Look at me, never rat on your friends and always keep your mouth shut.”