These Are The Most Legendary Gangsters In Cinematic History

You might not like what they do, but you know you’ve got to love a good quality mafia boss when he makes an extraordinary performance on the big screen. They might be violent, scary, and downright cruel, but we all have a soft spot in our hearts for the Italian-American classic mobster and everything that he (or she) is. These are, hands-down, the most epic, interesting, and legendary mafia bosses who came alive on the big screen. Even though some of these characters are from decades ago, they are still alive in the hearts of the millions of fans of this genre and the movies we all know and love.  

1. Don Vito Corleone (Marlon Brando) – The Godfather

Of course we had to start with the father of movie-mobsters himself, Don Vito Carleone, played by the unmatched Marlon Brando. This character really encompasses what makes these mafia bosses such intricate (and dare we say, loveable?) characters. Although he is willing to maim, disfigure, and murder anyone who makes problems for his business or his family, he also cares deeply for his family which makes him hard to hate. 

2. Tony Soprano (James Gandolfini) – The Sopranos

With six full seasons of the Sopranos, it was easy for us to get to know the main character and boss of the “family”, Tony Soprano. We watched his children grow up, his therapy sessions and his relationships develop and change. Tony is a modern ‘90s man living in New Jersey, so it’s easy for us to relate to him, despite the unspeakable (and particularly bloody) punishments he’s dolled out over the years. Also, his love of animals and babies really makes us feel for the guy.

3. Tony Montana (Al Pacino) – Scarface

“Say hello to my little friend” is the iconic line that everyone remembers from Scarface, which was, of course, followed by a machine gun blasting rounds across the room. Tony Montana, played by Al Pacino, makes a pretty terrifying drug lord gangster. His love for money (and cocaine, of course) trump all, and he makes it very clear that he will get rid of anyone who gets in his way. It’s easy to hate this character, but you have to admire his passion. 

4. Tommy DeVito (Joe Pesci) – GoodFellas

It seems like whenever Joe Pesci plays in one of his many successful mobster roles, his character is completely ruthless and short-tempered. And it’s no different with his portrayal of Tommy in Goodfellas. Tommy is super aggressive, extremely violent, and totally ruthless when it comes to hurting or killing others. Like a true psychopath, Tommy doesn’t even bat an eyelash when there are fingers to crush or heads to smash in.

5. Al Capone (Robert De Niro) – The Untouchables

For Italian-American history fans, Al Capone was a real gangster during the 1920s and is still known as one of the most notorious mobsters in history to this day. In the movie The Untouchables, Robert De Niro takes on this legendary character as does an excellent job of telling his story. He gives a thrilling performance and gives us an authentic look at the life of Capone during Prohibition, as he took over a whole city and had it in the palm of his hand. 

6. Nicky Santoro (Joe Pesci) – Casino

Although he’s not the main character, Joe Pesci’s character Nicky Santoro is definitely the most gangster in this movie. As is his forte, Nicky is an angry, violent man with a short temper. He is enlisted as the guy who makes sure everyone is cooperating (if you know what we’re getting at), but his violent tendencies become even too much for the man who hired him (his best friend, Sam). In this movie, you can see Nicky do everything from stabbing someone in the throat to exploding someone’s head in a clamp. 

7. Frank Costello (Jack Nicholson) – The Departed

Frank Costello is an unforgettable character who is nothing short of a total psychopath. This is one of Jack Nicholson’s best performances, as he plays an Irish-American gangster boss who grooms one of his people to become a rat for the Massachusetts police department. Costello is violent, crazy, and completely unpredictable. He demonstrates this sentiment most with the line: “One of us had to die. With me, it tends to be the other guy.”

8. David “Noodles” Aaronson (Robert De Niro) – Once Upon A Time In America

This movie starts when Jewish ex-gangster, Noodles, is already an old man who returns to New York. However, it shows us flashbacks of his story as a gangster and career criminal during the 1920s and 1930s. As he had grown up in a Jewish slum and lived a tough life, it’s no surprise that Noodles became a hardened criminal who wasn’t afraid to hurt or even kill whoever got in the way of his money. 

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