Most Gangster Movie Ever: Field of 64

A note from the Selection Committee: In order to avoid any personal bias that may have influenced the seeding of these films, I devised a very sophisticated and complex formula using both the  Tomatometer of Rottentomatoes.com, which represents the critics’ consensus, and the website’s general audience score, with more weight being given to the latter because it’s all about the fans. 

Concerning the selection of the sixty-four movies, that was the result of a combination of personal knowledge and a little research.  There are always snubs during the March Madness selection process and I’m sure this one will be no different. 

To fill the 64 slots with competent flicks, I stretched the traditional understanding of a gangster movie to include those that may be less mob or gangster-centric but still contain traditional elements of those films such as hitmen, narcotics, criminal activity by close-knit groups, etc.

 

There were only two deal-breakers for the selected tourney participants: 1) No westerns and  2) No film that predates 1972.  Though there are many notable gangs and gangsters in the Old West cinema, westerns are a completely different genre and feel like a totally different kind of “gangster,” with all due respect Mr. Holliday.  There are no movies on this list release before 1972 because it’s when The Godfather whit the cinematic scene, which changed the game for this type of film.  And while there are plenty of worthy movie mobsters that proceeded the classic flick, most people don’t care about them.

No need to fret though.  There are plenty of gangster flicks left to fill our bracket.  And here they are…..

(In alphabetical order)

25^th Hour (2003) It’s Spike Lee and Edward Norton.  The late, great Philip Seymour Hoffman, Barry Pepper and Rosario Dawson.  It’s an F-you rant that’s one of the best scenes in the tournament.      

                                                

Above the Rim (1994) A story about G’s under the guise of a basketball flick.  Make no mistake, Birdie and his crew make this movie as gangster as any.  All naysayers will be subject to carzy hard, scar your tail bunks! 

       

American Gangster (2007) Famed film critic Devin Faraci said of American Gangster that it would someday be remembered in the same light by its generation as Goodfellas is remembered by its own.  Frank Lucas and family are prepared to “blot” out the rest of the competition to prove Faraci right.  

         

American History X (1998) Not your traditional gangster film but gang-related nonetheless.  Is it Edward Norton’s best performance?  It’s definitely his most gangster.  

            

Amores Perros (2001) The Mexican film intertwining three intriguing tales of dogfighting, a horrific car crash, and gangster sicarios.

Animal Kingdom (2010) Australia’s answer to Goodfellas, complete with its own terrifying, Pesci-esque character Uncle Pope.  Yes, it’s that legit.

           

Belly (1998) No other movie in this tournament has a bigger discrepancy between critics’ and movie-goers’ opinions (13% to 88%, respectively).  With a middle finger to the man and a faithful following behind it, Belly enters the field of 64.  

           

Black Mass (2015) Johnny Depp embodies the chilling spirit of Boston’s most notorious gangster, Whitey Bulger.  

Blow (2001) To win any tournament you need a little luck.  Maybe in this particular tourney we can call it “being connected” as opposed to being lucky.  Having said that, small-timer George Jung is connected all the way to the top of the Columbian drug cartel and one Pablo Escobar.    

          

Boondock Saints (1999) Before Norman Reedus  was Daryl Dixon and knocking off zombies on The Walking Dead, he was Murphy Macmanus head-hunting mafia gangsters in Boondock Saints. 

         

Boyz N the Hood (1991) A classic in its own right, the boyz from South Central L.A. will have no problem going toe-to-toe with mob legends.

A Bronx Tale (1993) Chazz Palminteri has never been more gangster with iconic lines like, “I did this to you!” and “Now yous can’t leave.” 

Carlito’s Way (1993) Carlito Brigante is a legend in el barrio and an even bigger legend on the silver screen.  Props for putting Puerto Rico on the gangster grid.

Casino (1995) Don’t insult this film by calling it “Goodfellas 2”, or you may get buried alive in the desert after being beaten within an inch of your life with aluminum baseball bats.    

      

                                                       

City of God (2003) Lil’ Ze is one of the most ruthless gangsters you’ll ever see on film.  The movie is one of the best you’ll ever see in your life.

Clockers (1995) Spike Lee gets another nod in the tournament with Clockers, an underappreciated film about a young drug dealer navigating the projects of Brooklyn.  

      

Collateral (2004) Tom Cruise as a grey-haired hitman running roughshod all over L.A.?  And I get wolves too?  Yes, please.                                                 

Colors (1998) A look at Crips and Bloods relations in 1980’s Los Angeles, in which Don Cheadle plays a soulless, ruthless Crip leader named “Rocket.” 

 Dead Presidents (1995) Normally you’d think that having one of the best soundtracks ever wouldn’t help a film’s street cred. But with names like Isaac Hayes, Barry White, Aretha Franklin, and Al Green, this gangster compilation is an exception to the rule.  Plus, that armored truck hit alone is worth a spot in the tourney. 

            

The Departed (2006) Perhaps the most re-watchable gangster flick in the tourney, The Departed is one of those rare instant classics. 

               

Donnie Brasco (1997) Nothing fugazy about this flick.  It’s as real as any mob movie in the tourney.  No, I mean it’s literally based on a true story. 

        

Drive (2011) Imagine a movie so gangster it only needs a pretty boy turned “about-that-life” boy Ryan Gosling and a few lines of dialogue.  It’s “all about that action, boss.” 

      

Eastern Promises (2007) You know you’re a “G” when you get into a knife fight to the death butt-naked in a Russian sauna. 

Gangs of New York (2002) About as old school as it gets when it comes to gangs in this country.  The Dead Rabbits were about that life before the 20^th century, and Bill the Butcher probably wrote the book on how to be a “G.”  

        

The Godfather (1972) The quintessential mob movie, the standard and a heavy favorite.  But is it more name than substance?  Is it time for a new boss? 

The Godfather II (1974) Arguably better than the original, and the original is one of the greatest films ever made.

The Godfather III (1990) The red-headed stepchild of the iconic trilogy is more gangster than suckers give it credit for.  It’s still Corleone.  

Gomorrah (2008) Writer Roberto Saviano received death threats from the Neapolitan mafia for exposing their activities in the novel and movie and is now permanently under police protection.  Gangster.   

  

   

Goodfellas (1990) Scorsese’s take on the New York mob did what no other gangster flick before it could do: hold a candle to The Godfathers. 

   

Gotti (1996) HBO’s production depicting the rise of the most beloved mafia boss in America’s history is spot-on and a must for mob film lover.    

                   

Heat (1995) Heat may lay claim to the best shootout scene in the tourney.  Now that’s saying something!

A History of Violence (2005) This overlooked, thought-provoking gangster movie is violent enough to hold its own against any of the top dogs in the syndicate.

Ichi the Killer (2001) Bizarre, disturbing, Japanese, and gangster as all get-out.  Ichi is one “G” you’ll never forget. 

   

Infernal Affairs (2002) If it weren’t for Infernal Affairs, there’d be no Departed.  It’s also widely considered to be better than its predecessor.  

King of New York (1990) Christopher Walken is the most lovable type of gangster, a Robin Hood mentality allows this fresh-out-of-prison drug lord to lay waste to his competition and distribute the spoils to those less fortunate.  Aw.

Lawless (2005) The only entry in the field of 64 that stars Shia LaBeouf.  That’s gangster enough.  

       

Layer Cake (2005) The G’s across the pond are making a splash in this year’s field.  Here it’s Daniel Craig and Tom Hardy, a more than formidable gangster combination.

        

Leon: The Professional (1994) Leon is maybe the best hitman in a tournament full of some of the greatest to ever do it.  A true professional “G.”  

Lock, Stock and Two Smoking Barrels (1999) Don’t get it twisted: London’s East End is home to some of the game’s most notorious gangsters.  At least they can make you laugh while they break your fingers one by one.

El Mariachi (1993) The little-known prequel to Desperado.  Don’t think it has a chance?  This movie was made for $10,000; it can do anything.   

           

Mean Streets (1973) De Niro’s Johnny Boy in Means Streets is not unlike O-Dog in Menace II Society.  Unbalanced and unpredictable always make for the scariest gangsters.         

      

Menace II Society (1993) Quotable lines abound in this Boyz N the Hood-companion piece that may be a colder, grittier, and more accurate depiction of life in South Central Los Angeles. 

      

  

Miller’s Crossing (1990) The Coen brothers try their hand at the mob film genre and the end result is one underrated gem of a movie about made men. 

    

Mystic River (2003) The mob movie experience makes its way to Boston again where Sean Penn is cold and calculated and cares nothing about childhood friendships when it comes to revenge.       

       

New Jack City (1991) Nino Brown is as bad as they come.  And he and his crew will have no problem taking other would-be gangsters flicks out in broad daylight.  “Rock-a-bye, baby.”

No Country for Old Men (2007) Anton Chigurh is like that really special player for that unknown team that makes a splash once the nation sees him on the big stage.  That’s not to say that no has ever seen No Country, but in terms of a “gangster film,” it’s not really what you’d consider a household name.  I present to you the Steph Curry and Davidson of this year’s big dance.  

          

Oldboy (2005) Oldboy will knock you on your wire-tapped, rat-smelling arse, then pull out your teeth one by one until you acknowledge it as one of the most gangster movies ever!   

               

Once Upon a Time in America (1984) Underappreciated to say the least.  It’s De Niro and James Woods in the story of a Jewish gangster in Prohibition-era New York, and it’s worthy of a mention among the greats.   

 

A Prophet (2010) The fact that A Prophet hasn’t been seen by so many is perhaps the biggest crime in any of these films.  It’s legitimately as good as any of the tourney favorites. 

Pulp Fiction (1994) Tarantino’s most beloved film has some of history’s most memorable, impressionable gangsters.

Reservoir Dogs (1992) Quentin’s first film is probably his most gangster, ending in classic Tarantino Mexican standoff style.  And if I just spoiled the ending of Reservoir Dogs for you, you’re in the wrong tournament.

Road to Perdition (2002) Tom Hanks as a hitman: check.  Legendary Paul Newman as a mob boss: check.  Inevitable intense showdown by the two in the pouring rain: check.  Ticket to the Big Dance: cashed.

Scarface (1983) The very definition of “crowd-favorite.”  Tony Montana does it for the fans.  And probably for the money.    

    

Set it Off (1996) They’ll be no underestimating these women by other tourney participants.  These ladies have knocked over enough banks and “put in enough work” to earn a spot among the most notorious of cinema’s gangsters.   

Sexy Beast (2000) Ben Kingsley was nominated for an Oscar for his performance as unhinged and brutal yet sometimes comical gangster Don Logan.  He didn’t win, so he’s out to claim another piece of hardware: the Most Gangster Movie Ever title!  

     

        

Sin Nombre (2009) Real talk: most people need to watch more foreign flicks.  These gangsters south of the border ain’t nothing to play with, as evident by the feeding of a rival member’s insides to dogs…..    

Snatch (2001) “Franky Four Fingers,” “Bullet-tooth Tony,” “Boris the Blade,” “Turkish,”….. these gents to G’s name-game is off the chain.  But these Brits ain’t all show and Brad Pitt is golden as an Irish gypsy who’ll knuckle up on anyone in the brackets.         

   

Straight Outta Compton (2015) Don’t scoff at the new kids on the block.  And don’t tell them I called them that either.  Compton may be a new film, but its subject is as gangster as any other entry in the tourney.    

             

The Town (2010) Boston is representing, this time from the neighborhood of Charleston, which churns out small-time gangsters like Kentucky churns out one-and-done’s. 

            

                              

Training Day (2001) I don’t care if they’re cops.  Alonzo Harris and company are cut from the same cloth as other cinematic crime crews.  Don’t think they can win it all?  They’re the Po-lice!  These other thugs will be playing basketball in Pelican Bay before it’s over. 

       

True Romance (1993) So what’s gangster about a Tarantino script directed by Tony Scott?  How about Christopher Walken as a Sicilian drug dealer and Gary Oldman as some sort of Rastafarian pirate pimp named Derxl Spivey.

The Untouchables (1987) Who are the real G’s here?  Capone’s crew or Ness’s custom crew of killers?  Doesn’t matter.  Movie’s gangster.

The Usual Suspects (1995) Not many names strike fear in the hearts of snitches like that of Keyser Söze.  And that ending may be the most gangster in cinematic history!

The Warriors (1979) The Warriors “bopped” their way from Brooklyn to Coney Island, wasting the best gangs New York had to offer along the way.  No other squad is more prepared for a knockout style tournament.