Cigar Aficionado

It's the screech of brakes, the deadly chatter of a machine gun and the squealing tires and roaring engines of a getaway car.

It's fedoras and double-breasted suits, gats and bootleg whiskey in smoky dives, brass knuckles and wise guys, Prohibition and the War on Drugs.

Say the words "gangster movie" and vivid images spring to mind. They can be from the 1930s: Edward G. Robinson wailing "Is this the end of Rico?" or Jimmy Cagney, pelted by rain, dying as he falls face first to the pavement. Or from the modern era: Marlon Brando calmly stroking a cat in The Godfather, Joe Pesci viciously plunging a butcher knife into a rival he's stuffed in the trunk of a car in Goodfellas, or Al Pacino yelling, "Say hello to my little friend" before unleashing a flurry of automatic-weapon fire in Scarface.

The gangster movie is that uniquely American blend of art and entertainment that has been adopted and adapted around the globe. Violent, bloody, cruel, witty, moralistic or amoral—moviegoers can never seem to get enough of the lives (and deaths) of criminals, or at least the outsized bad guys who populate Hollywood's steady output of stories which, once upon a time, preached the message that crime doesn't pay.

Gangsters, mobsters, criminals, goons, hoodlums, hooligans and thugs have always been a part of movies. "One of the first films ever shown was The Great Train Robbery [1903]," says Terence Winter, executive producer of "The Sopranos" and creator of "Boardwalk Empire," two TV series that helped redefine the gangster genre. "Bad guys have been fascinating from the beginning of cinema."

The oldest surviving gangster silent film is The Black Hand, from 1906. D.W. Griffith made a short silent gangster film, The Musketeers of Pig Alley, in 1912, and well-dressed toughs were a staple of silent comedies as well, as foils to comics such as Charlie Chaplin and Buster Keaton.

"The gangster has eternal appeal because of the glamour associated with the lifestyle," says film historian Jeanine Basinger, former chair of the film department at Wesleyan University. "It's the hat, gloves, suit and the camel coat, the fancy cars. He goes to nightclubs with beautiful women and smokes fine cigars."

Writer Gay Talese, whose 1971 book Honor Thy Father offered one of the first looks inside the modern world of organized crime in America, says, "Gangster films are really urban westerns. But instead of having horses, they ride in limousines. Plus, most people feel as though the law is unfair in some way. So those who flaunt the law become heroes, in a way."

Two things wrestled the gangster film into its earliest, most vibrant form: the advent of Prohibition, which galvanized criminals into organizing enterprises to sell illegal alcohol, and the arrival of sound in films. Prohibition led to the rise to power and infamy of crime bosses like Al Capone (brought to life on-screen by, among others, Robert De Niro, Rod Steiger and Ben Gazzara) and the various crime families created the characters, the stories, the backdrop for that first generation of gangster films.

Talking pictures, however, gave those stories their voice.

"The genre we call ‘gangster films' needed sound," says Basinger. "The sound of the machine gun, the way these characters talked with the ‘dese-dem-dose' diction—sound made a great difference."

Gangster films of the 1930s created the hard-boiled mold that captured the American imagination during the Depression, when movies were a form of refuge. The films created an early wave of movie stars who became identified with the genre (and, occasionally, struggled to shake its image): Robinson, Cagney, Humphrey Bogart, George Raft.

"I remember watching those old movies on TV when I was growing up," Winter says. "Things like Angels With Dirty Faces, The Roaring Twenties—I saw enough of them that I started to really recognize the actors that I liked. So occasionally it was confusing when I'd see Cagney or Bogart in a straight role. Wait—what? You mean he's a lawyer now?"

But as times changed after World War II, the gangster film underwent a transformation. Arthur Penn's Bonnie and Clyde (1967), with good-looking stars Warren Beatty and Faye Dunaway, presented criminals as celebrities, fashion plates who could, in a blink, turn into killers. The film offered one of the bloodiest finales to that point in film history, a sharp contrast to the almost happy-go-lucky existence these bank robbers lived for most of the film.

"That was a big changing point," Basinger says. "Here was a film about characters with complicated psychology. The ratings system, which was new at that time, eliminated most censorship. So you had this very complex psychological portrait, and you were able to tell it with the kind of bloody action that was very new."

Then, in 1972, Mario Puzo's best-selling novel, The Godfather, burst on to the screen in an adaptation by Francis Ford Coppola.

"I saw The Godfather when I was 17 and it blew me away," says Kyle Smith, film critic for the New York Post. It was so operatic and tragic."

Adds Winter, "I saw it when I was 12; it was rated R, but my sister wanted to see it and she took me with her. Needless to say, it made a pretty big impression."

As Talese observes, "The Godfather was like Gone With the Wind—this classical, epic film—and it was one of the great movies. Of course, people think they understand the Civil War after seeing Gone With the Wind—and they think they know the Mafia because they've seen The Godfather. There's enough truth in those films to be believable—but that doesn't mean they're real."

The Godfather, Basinger notes, consciously elevated the gangster film: "It made it operatic," she says. "It was something epic. It was no longer a fast, cheap little thing—it became art."

Until Coppola worked his cinematic magic, gangster films may have been popular, but they rarely earned the kind of critical hosannas that greeted Coppola's film (and its sequel, which, to many people, is an even better film). Until that time, gangster films were dismissed as genre potboilers, simplistic good-v.-evil morality tales or melodramas, minus nuance or artistry.

"Howard Hawks' Scarface [1932] was a work of art without trying to be," Basinger says. "With The Godfather and gangster films, it was like the starlet who finally wins the Lifetime Achievement award. It lifted the genre out of being just about gore and excitement. The Godfather was the first time you saw the complexity of crime as a business."

The Oscar-winning film and its sequel were game changers, creating a new generation of gangster movie stars (Pacino, De Niro) as well as directors (Coppola, Martin Scorsese, Brian De Palma). The Godfather also transformed not just the way that the average person thought about gangster films, but the way gangsters thought of them as well.

"One of the funniest things I've ever read was about an FBI wiretap on a meeting of a group of Mob bosses," Winter says. "The wiretap reported that, during the meeting, they were playing ‘Theme from The Godfather' on a loop, over and over. It was their theme music, apparently. So there you have art imitating life imitating art."

Scorsese's Goodfellas (1990) also proved a turning point, Smith notes: "If anything, The Godfather raised these people to a level where they don't belong. It was Shakespearean—but they were basically thieves. But Goodfellas doesn't have that: These guys don't believe in anything. They're just criminals. And it brought out a comic element, something Scorsese did really well. In a lot of ways, Goodfellas is a really funny film."

If there's a moment that the gangster film launched itself into the 21st century, it would be the January 1999 debut of "The Sopranos" on HBO. Cited as the first example of a new golden age of television—when cable and pay—cable television came into its own as an alternative to the movies for long-running stories about complex characters-"The Sopranos" examined the modern American organized crime family, from both a business and personal perspective.

"It was one of the first accurate depictions of what it would be like to go home with a gangster," says Winter, who wrote and produced for the show from 2000-2007. "The Godfather was so operatic that most people couldn't relate to that lifestyle. But ‘The Sopranos' peeled back the curtain on their mundane lives, in the same way that Goodfellas did.

"People would be shocked at how well they related to this guy who ran a crime family. They'd watch Tony and think, ‘He has the same problems with his kids that I do' or ‘He and his wife argue the same way I do.' It was the first time a show clued us in to the humanity of these people. Of course, every time people would get lulled into thinking Tony was this big, cuddly bear, you'd be reminded that, at the end of the day, he'll go out and break somebody's leg because they owe him money. And you think, ‘Oh yeah...' "

Having thoroughly explored the world of the modern gangster in "The Sopranos," Winter's next project offered a bit of time-traveling: "Boardwalk Empire," which went on the air in 2010 and ran for five seasons, started its story in 1920 and looked at the rise of organized crime at the onset of Prohibition, when everything was up for grabs.

"By the time ‘The Sopranos' come along, things are really organized—but with ‘Boardwalk Empire,' we got to see the beginnings of that," Winter says. "Back then, things were really disorganized and there were a lot of different factions. Before Prohibition, organized crime was mostly about election rigging, embezzling, strong-arm activities. Once Prohibition came in, they organized around the illegal sale of alcohol. That made criminals wealthy and they were able to infiltrate other enterprises. So with this series, we were able to see the architecture of organized crime."

Where does that fascination with criminal activity come from? In part, it's built on the nature of movies themselves: the thrill of watching someone do things we've all thought of doing but would never do, either out of conscience or fear of getting caught.

"It's a way of living vicariously through someone who is engaging in activities you would never engage in yourself," Winter says. "You know how you were always attracted to the kid in class who acted up or made wisecracks? And you'd think, ‘How can he do that?' The gangster is the ultimate expression of that."

"That's the great thing about movies: You get to spend 90 minutes with these criminals," says Basinger. "For 85 of them, they're killing and robbing. And then, for five minutes at the end, they pay the price. So the viewer gets to have it both ways: the jolt of excitement and violence, but knowing they get what's coming to them in the end.

"America has a tradition of glamorizing outlaws...We are, after all, an outlaw nation—we're a people who defied the European establishment and created a new country. So it appeals to us to see people who defy authority. They're part of the American mythology."

Adds Winter, "A regular person with a job looks at Tony Soprano and here's what he sees: His office is in the back of a strip club. He eats what he wants, he drinks what he wants, he sleeps as late as he wants—and he has sex with whoever he wants. You have to admit, that looks pretty appealing."

Almost too appealing: film critic Kyle Smith drew heated responses when he suggested that films like Goodfellas were strictly a male province, a taste that men come by naturally and that women have trouble appreciating. In an article titled "Women Are Not Capable of Understanding Goodfellas," he wrote, "To a woman, the Goodfellas are lowlifes. To guys, they're hilarious, they're heroes. They rule the roost."

In an interview, Smith says, "Movies about people living at the extremes of society are much more welcomed by men than women. Women see themselves as more a part of society or a family unit. Men see themselves as loners. These characters exchange sharp dialogue, they banter, they joke around—and that makes them appealing, even though we know they're psychotic criminals."

Over the years gangster movies proved to be a mixed blessing for actual gangsters. Depicted in the films as living a highlife of luxury goods afforded by an endless stream of ill-gotten cash, real-life gangsters felt a certain pressure to live up to the image that Hollywood created for them.

As he was writing Honor Thy Father, about a civil war within New York's Bonanno crime family, Talese says he found himself moved by one particular scene he witnessed: "Here was a Mafia wife, complaining to her husband that she didn't have enough money to buy clothes for the children or to pay the dentist," he says. "You never think of these as being the kinds of concerns a Mafia wife would have. Gangsters have cars and all the other trappings of success and wealth on film, but that really wasn't true for most of them in real life. But the men were living this life that was projected on them—so sometimes, they overspent, faking affluence."

In essence, gangster films mirror the forces that shape the world. "All war is about power, prestige and access to markets," says Talese. "It doesn't matter if you're talking about the Ukraine or Afghanistan—it's all about territory and access to markets, which is also what the Mafia is about."

The gangster film is about more than just the Mafia, and it continues to thrive because it can adapt to so many milieus. Consider 1990's Men of Respect, in which John Turturro played an ambitious capo who bore a striking resemblance to Shakespeare's Macbeth. Or Scorsese's The Departed, an Oscar-winning tale of contemporary gangsters that was adapted from a Japanese gangster film-inspired by American gangster films.

The long history of organized crime in America provides numerous entry points to a gangster story, from Scorsese's Gangs of New York, which dealt with 19th-century criminal gangs, to Mario Van Peebles' New Jack City, which used the rise of crack cocaine in New York as the backdrop for its cops-v.-gangsters tale.

The gangster movie is a genre that seems to have room for all sorts of permutations: from comedy (Analyze This) to darker comedy (In Bruges) to comic-book adaptation (Road to Perdition), from coming-of-age stories (Mean Streets) to hard-boiled crime tales (The Town).

It also seems to continually reinvent itself. Quentin Tarantino makes postmodern gangster films, such as Reservoir Dogs and Pulp Fiction. Director Guy Ritchie did a similar remodeling job on the form with his fast-paced British gangster films, including Lock, Stock and Two Smoking Barrels, Snatch and RocknRolla.

And the genre will get a new jolt this fall with Black Mass in which Johnny Depp will play real-life Boston bad guy Whitey Bulger.

"As a genre, I think it's a perennial, rather than a cyclical thing," Winter says. "It's a genre that's every bit as legitimate as the western or the romantic comedy."

"Is this genre still viable? Well, it's hard to do one with quality," Basinger says. "Because, really, it comes down to the quality of the storytelling. It's about getting it done well and marketing it right. But there's always an audience for a good one." 

Contributing editor Marshall Fine writes about film and entertainment at his website, www.hollywoodandfine.com. Follow him on Twitter @hollywoodnfine.