Sean Penn as Mickey Cohen in Gangster Squad (2013). Photo by Wilson Webb/Warner Bros.

Imagine Mickey Cohen. West Coast gangster kingpin, 1940s and ’50s. Gambler. Tax cheat. Mob enforcer. Major racketeer, with hands in prostitution and dope. Volcanic temper. Not the kind of guy you’d want to chat with over the backyard fence.

And nasty as all get out is how Sean Penn plays Mickey Cohen in Gangster Squad, opening in January, about Los Angeles police chief William Parker (Nick Nolte) and his elite squad (including Ryan Gosling and Josh Brolin) whose mission is to keep the West Coast mob, as represented by Cohen and his minions, out of the city. It’s a standard plotline—cops vs. hoods—but the release of the movie is just the latest proof that when it comes to screen portrayals of mobsters, real or imagined, Americans enjoy wallowing in all that anti-social behavior. Gangsters are individualists on steroids, and we can’t get enough of them.

“There’s something enticing about the world [gangsters] live in,” says Gangster Squad director Ruben Fleischer. “It’s this forbidden existence; they live life on their own terms. Gangster films make the bad guys the good guys.”

“We like people who have more power, more id, less super ego,” adds Stuart Fischoff, senior editor of the Journal of Media Psychology. “There’s a bit of a gangster in all of us. We can vicariously identify [with them], live out our fantasies.”

Guess what? It didn’t take filmmakers very long to recognize this. As early as 1912, D.W. Griffith’s The Musketeers of Pig Alley showed a fascination with organized crime on New York’s Lower East Side, and allegedly used real street gang members as extras. But it was the Great Depression, and the gangster films of that era, which really jump-started the genre: Edward G. Robinson in Little Caesar. James Cagney in The Public Enemy. Paul Muni as Scarface and Humphrey Bogart as Duke Mantee in The Petrified Forest. Snarling nasty guys with their guns, molls, Prohibition-era chicanery, and personal charisma. All of which came out of a specific cultural and political context. Desperate times created desperate characters, and the collapse of the worldwide economic system caused many people to question the viability of the capitalist system—and their place in it.

Edward G. Robinson in Little Caesar. Photo courtesy www.doctormacro.com.

“The early gangster films reflected the crisis of individualism in the Depression,” says film critic Dave Kehr of davekehr.com. “If you wanted to rise above, you had to go outside the law. Gangster films parody capitalism, they highlight class distinctions. It’s the anti-American dream.”

“If you go back to the 1930s, America was becoming more urban, there was the Great Depression, and Americans felt the economic system had failed them, so people like John Dillinger became folk heroes,” adds Glen Macnow, co-author of The Ultimate Book of Gangster Movies.

“The film audience was ethnic and urban,” he adds, “so Warner Brothers started the genre by giving the urban immigrants something they liked, with pictures featuring urban ethnic criminals like Scarface and Little Caesar. You had this perfect formula for success.”

Warren Beatty and Faye Dunaway star as Bonnie and Clyde (1967). Photo courtesy Warner Bros./Seven Arts/Photofest.

And that’s pretty much how the gangster film played out over the next few decades. The bad boys remained individualists involved in all sorts of rackets, and as the Depression waned, the genre shifted into the bleak moral atmosphere of film noir, where, says Macnow, “the gangsters are less gunmen than businessmen running corrupt businesses.” Every once in a while there’d be a psychological take on the genre—James Cagney’s psychopathic mama’s boy in 1949’s White Heat—or, in the case of 1967’s Bonnie and Clyde, a film that startled with its violence and sociological insight.

“You got into the psychology of those people,” says Fischoff of Bonnie and Clyde. He explains how this particular twist on the gangster flick delved with Freudian insight into the roots of the characters’ pathology. The message was that “people weren’t born villains.”

Then came one of those great breaks from the past, as significant in cinematic terms as when dinosaurs seemed to disappear from the planet almost overnight. 1972. The Godfather. On one level, you can think of it as the heartwarming tale of an Army vet who goes into the family business. On another, it’s the tragedy of an honest son who evolves into a ruthless crime boss. All told in a groundbreaking, operatic style that took a trash novel and turned it into cinematic high art.

Marlon Brando in The Godfather (1972). Photo courtesy Paramount Pictures/Photofest.

Director Francis Ford Coppola’s classic film also represented a major shift in the underlying theme of the gangster flick. The game changed from “radical individualism to the pleasure of belonging to a group with special privileges,” says Kehr. “These were the guys excluded from society, constructing their parallel world where they’re safe and empowered.”

“The Godfather was an epic, a family saga, a Shakespearean tragedy,” adds Macnow. “It turned the Mob from a bunch of nasty thugs and turned them into a modern view of Roman royalty. It’s about family and honor and code.”

The Godfather led directly to Goodfellas, in which mobsters are family surrogates for Henry Hill, the lead character. And to The Sopranos, the groundbreaking blend of suburban psychoanalytic angst with the conventions of the mobster story. Even the Al Pacino classic, Scarface, certainly one of the most florid and over-the-top gangster movies ever made, dabbled in family dynamics.

These are our top-rated films documenting true-to-life nasties.

Click image to enlarge infographic.

So what’s left? The gangster film has been around for 100 years, morphing from stylized Depression-era tales of social consciousness to contemporary stories owing their popularity as much to family doings and the analyst’s couch as “going to the mattresses” and contract killings. In some ways, it seems the genre has exhausted itself, and contemporary audiences are more interested in tales of super heroes and alien slime things.

Which in some ways makes Gangster Squad a bit of a throwback, a nostalgia piece about the days when mobsters were predominantly Italian or Jewish—at one time the underdog, immigrant groups of a bygone era. But crime is ever resourceful, and so are our filmmakers. And as American demographics continue to evolve, its criminals will reflect that evolution. Which means that changing demographics have affected what kinds of villains we’re seeing onscreen, because the audience has changed. Now there’s plenty of room for films about Cuban dope dealers (Scarface), African-American drug masterminds (American Gangster), Russian crime families (Eastern Promises), and streets gangs of various ethnicities and races (Boyz n the Hood, Colors).

Can the movies about Nigerian, Albanian, and Chinese crime lords be far behind?

“We have always been fascinated with the guy who chooses to live his life on his own terms,” says Macnow, “We all want to believe we’re rebels, so when we root for the gangster, we get that vicarious thrill.”

Adds Fleischer: “America is a place that embraces liberty, and the right to live life on your own terms. People have looked up to these bad guys who are not following the rules. It’s safer to do that in movie form than reality.”

Mob Love The Saturday Evening Post

Sean Penn stars as real-life gangster Mickey Cohen.

Mob Love

(Lewis Beale, Sep/Oct 2012)

The classic toughs of the silver screen are the ultimate individualists. These are guys who know no boundaries when it comes to fulfilling their ambitions. For Americans, it’s a formula impossible to resist.

George Raft (right) became a star after his performance in the movie Capone.

Out of My Past

(George Raft, September 21, 1957)

Hollywood’s mysterious tough guy reveals he was once a gun-toting consort of underworld big shots. Here, finally, Raft tells the truth about his life as a young gangster.

Al Capone smiled on his way to prison in 1932.

Big Shots or Pop Guns?

(Post editors, August 15, 1931)

Post editors wonder if the arrest of Al Capone would lead to the end of the gangster era in books and film.

Mae Clarke and James Cagney in Public Enemy.

How I Got This Way

(James Cagney, January 14, 1956)

James Cagney knew what it was to flop on Broadway, but won overnight movie fame as a gangster who mashed his moll in the face with a grapefruit.

Giesler (left) with his client Bugsy Siegel.

I Defend a Mobster

(Jerry Giesler, December 12, 1959)

Jerry Giesler, a celebrated Hollywood lawyer, discloses how he sprang Bugsy Siegel from a murder charge in 1959.

Hollywood and Gangsters The Saturday Evening Post

The article below is a small peek into Giesler’s famous career and covers the tale of his relationship with the man once known as one of the “six most dangerous gangsters in the United States.” Notorious mobster: Bugsy Siegel.

Click here to download “I Defend a Mobster,” or read below.

I Defend a Mobster The Saturday Evening Post