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Family films: The most entertaining gangster movies
Paramount Pictures

Family films: The most entertaining gangster movies

The gangster film is a subcategory of crime film. Although, they aren’t all serious necessarily, as gangster comedies do exist. Call them mobsters or what have you, but they are decidedly gangsters. While such criminal enterprises aren’t exactly fun in life, there are many entertaining gangster movies out there. These are some of those films.

 
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“The Godfather” (1972)

“The Godfather” (1972)
Paramount

“The Godfather” is the pinnacle of cinema to many. It’s considered one of the best films ever made. Francis Ford Coppola’s movie won Best Picture, among other Oscars. However, it’s not entirely high-minded, and there is some action and exciting stuff in the mix to make “The Godfather” even more entertaining.

 
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“The Godfather Part II” (1974)

“The Godfather Part II” (1974)
Paramount

We don’t have any other sequels on this list, but we had to include “The Godfather Part II.” After all, like the original, it won Best Picture. Some consider the sequel even better than the first movie. As such, we had to have it on the list.

 
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“Goodfellas” (1990)

“Goodfellas” (1990)
Warner Bros.

Martin Scorsese’s “Goodfellas” is, in turn, exciting, tense, funny, scary, you name it. The movie really runs the gamut. Next to Coppolla’s first two “Godfather” movies, there is no gangster movie held in more esteem than “Goodfellas.”

 
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“My Blue Heaven” (1990)

“My Blue Heaven” (1990)
Warner Bros.

“Goodfellas” is based on the life of Henry Hill. Nicholas Pileggi wrote the book “Wiseguy,” the basis of “Goodfellas,” by extensively interviewing Hill. Pileggi and Nora Ephron were married then, and she turned Hill’s stories into the screenplay for “My Blue Heaven,” a comedic take on a gangster in witness protection.

 
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“Analyze This” (1999)

“Analyze This” (1999)
Warner Bros.

This is already the third film with Robert De Niro in it on this list. Hey, the guy is a legend in this particular genre. “Analyze This” is a comedic take on mobsters, though. He and Billy Crystal were a duo that were fun enough the film got a sequel.

 
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“Carlito’s Way” (1993)

“Carlito’s Way” (1993)
Universal

Carlito’s Way” is largely based on the novel “After Hours,” but Scorsese had already used that title for a film. So, Brian De Palma’s movie takes some details, and the title, of an earlier book about the same character. “Carlito’s Way” stars Al Pacino as a criminal trying to go straight, which is proving difficult.

 
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“Casino” (1995)

“Casino” (1995)
Universal

So many of the usual names are involved here. Martin Scorsese and Robert De Niro, for example. This pseudo-follow-up to “Goodfellas” is a little overstuffed and a smidge too long, but it is still a really good film that would be the best gangster movie made by most directors.

 
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“Get Shorty” (1995)

“Get Shorty” (1995)
MGM

Elmore Leonard stories have some interesting criminal characters in them. Chili Palmer, for example, a loan shark who goes from Miami to Los Angeles to collect for his boss, but is so enamored by Hollywood he decides he wants to quit his gig and produce a movie. Of course, it’s not as simple as all that.

 
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“Johnny Dangerously” (1984)

“Johnny Dangerously” (1984)
20th Century Fox

There have been a few spoof movies making light of gangster movies. “Mafia!” doesn’t exactly work, as one example, but “Johnny Dangerously” mostly does. A lot of that is because Michael Keaton stars, and he showed why he was soon to become a massive movie star.

 
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“Snatch” (2000)

“Snatch” (2000)
Columbia

It’s time to go across the pond. Guy Ritchie loves himself a British gangster movie. “Snatch” was something of a sequel to his breakthrough film “Lock, Stock and Two Smoking Barrels,” but “Snatch” is a little more polished and thus a bit better.

 
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“Layer Cake” (2004)

“Layer Cake” (2004)
Columbia

J.J. Connelly wrote the screenplay for “Layer Cake” based off his own book. The unnamed protagonist deals cocaine in London, but he does it in a professional way that makes him stand out from some other criminals in his world. The film stars Daniel Craig, and reportedly it played a big role in his getting the part of James Bond.

 
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“Scarface” (1983)

“Scarface” (1983)
Universal

Before “Carlito’s Way,” De Palma and Pacino worked together on “Scarface.” It’s violent and over the top, and also Pacino is playing a Cuban immigrant for some reason. The film isn’t “good,” but it is entertaining and has become a favorite of many.

 
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“Some Like It Hot” (1959)

“Some Like It Hot” (1959)
United Artists

“Some Like It Hot” is included on some lists of the best gangster films, and it is an iconic comedy (that’s still funny at that) so we figured we’d include it as well. There is some sense to that. While the main characters are musicians not gangsters, the inciting incident is them seeing the Valentine’s Day Massacre took place. For the rest of the movie, Jack Lemmon and Tony Curtis are trying to outrun the mob.

 
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“Key Largo” (1948)

“Key Largo” (1948)
Warner Bros.

Let’s go old school, even older than “Some Like It Hot.” “Key Largo” is one of the films that Humphrey Bogart and Lauren Bacall made together. A group of people are stuck at a resort in Florida with a hurricane approaching, and things get complicated when it turns out one of the guests is Johnny Rocco, a vicious criminal on the run.

 
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“Heat” (1995)

“Heat” (1995)
Warner Bros.

Michael Mann likes to make movies about the professional aspects of being a criminal. “Heat” is the most-loved of those movies and is also more entertaining than, say, “Thief” or “Public Enemies.” Plus, it was the first time De Niro and Pacino shared the screen together, which made it an epic event.

 
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“Super Fly” (1972)

“Super Fly” (1972)
Warner Bros.

The Blaxploitation genre was rife with films about gangsters and mobsters, and “Super Fly” is near the top of that list. Bolstered by an infectious soundtrack, “Super Fly” is, yet again, about a big-time cocaine dealer who wants to go straight. Hey, “Super Fly” was out well before “Carlito’s Way” or “Layer Cake,” to be fair.

 
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“The Untouchables” (1987)

“The Untouchables” (1987)
Paramount

We think of Scorsese and Coppola when it comes to gangster films, but this is another De Palma movie. Maybe he belongs in the mix as well. “The Untouchables” focuses on Eliot Ness’ crew who were cracking down on rum runners during prohibition, specifically on Al Capone. Sean Connery won an Oscar for the film.

 
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“Bonnie and Clyde” (1967)

“Bonnie and Clyde” (1967)
Warner Bros.

Many point to “Bonnie and Clyde” as a turning point for American film. The movie, indebted in part to European cinema, was evocative and also unexpectedly violent for the era. “Bonnie and Clyde” is, as you likely surmised, about the infamous bank-robbing duo.

 
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“The Public Enemy” (1931)

“The Public Enemy” (1931)
Warner Bros.

In the pre-Code days of Hollywood, gangster films were abundant. “The Public Enemy” is arguably the best of the bunch. James Cagney and Jean Harlow, two icons of the era, costar. Cagney plays Tommy Powers, and the film chronicles his rise in the Irish mob.

 
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“The Departed” (2006)

“The Departed” (2006)
Warner Bros.

Another Scorsese film to end the list. For years, Scorsese couldn’t get a win for Best Director or Best Picture. Then, finally, it happened with “The Departed.” Now, maybe it was a bit of a career-achievement win, but Scorsese deserved that anyway. Plus, while it may not be on the level of “Goodfellas,” “The Departed” is quite good and pretty pulpy from an entertainment perspective.

Chris Morgan is a sports and pop culture writer and the author of the books The Comic Galaxy of Mystery Science Theater 3000 and The Ash Heap of History. You can follow him on Twitter @ChrisXMorgan.

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