This Wednesday, September 15, TCM presents “The Stars of Prohibition,” an evening of gangster movies set during the Roaring 20s. The “Stars” are not movie actors from the 1920s but gangsters, who became rich and powerful by providing liquor to the millions of Americans left parched by the 18^th Amendment.

Part of the fabric of the hedonistic Jazz Age and the tumultuous Depression era, gangsters such as Louis Lepke, Arnold Rothstein, Frank Nitti, Dutch Schultz, and Al Capone were both condemned and sensationalized in newspaper headlines, parlaying their notoriety into celebrity. Photos of gangster-related violence in the streets shared space with snapshots of famous athletes hobnobbing with Capone at the ballpark. These urban criminals, who were the product of big-city ghettoes where various immigrant groups struggled to survive, differed from outlaws like Dillinger and Bonnie & Clyde. Outlaws hailed from small towns or rural back roads, robbed banks or other business for quick cash, and were 20^th-century versions of mythic Wild West figures such as Jesse James or the Dalton Gang. Gangsters controlled vice crimes like gambling, prostitution, illegal liquor operations, and later drug trafficking. The gangster organizations had been operating in major urban areas for decades, but they became powerful, financially sound, and politically connected during Prohibition. Often mentioned in the same breath, the gangsters of the Roaring 20s and outlaws of the Depression actually have little in common, save for being pursued by the FBI and mythologized in popular culture.

TCM’s Wednesday line-up features five colorful b-films about big-name gangsters: Al Capone (1959) with Rod Steiger playing the real-life Scarface; The Rise and Fall of Legs Diamond (1960), starring Ray Danton as the New York gangster; King of the Roaring 20s: The Story of Arnold Rothstein (1961) with David Janssen (the title character of TV’s The Fugitive) as the kingpin of the Jewish mafia; Lepke (1975), starring Tony Curtis as the ruthless head of Murder, Inc.; and Mad Dog Coll (1961), featuring little-known actor John Davis Chandler as the hot-headed Irish enforcer, Vincent Coll.

Even before I moved to Chicago, where the city’s gangster lore is as ingrained in its residents as the Cubs-Sox rivalry, I had a soft spot for gangster films, primarily because many film historians posit the genre as a critique of big business. In this interpretation, organized crime and corporate America are two sides of the same coin, with the participants of each climbing the ladder of success rung by rung until they reach the upper levels of their respective organizations, where power, money, and prestige await them. Gangster success is the dark opposite to corporate success, with the former exposing the cutthroat tactics and immoral underpinnings of the latter. Perhaps this connection is why the archetype of the gangster is so attractive to us—he represents a perverted twist on the path to the American Dream.

In keeping with TCM’s theme of “The Stars of Prohibition,” I offer a list of some of my favorite films about gangsters and Prohibition. Some are not gangster movies per se, but all of them include a rip-roaring depiction of the familiar machine-gun-toting, bootlegging, and rum-running criminals that signify the Prohibition  era for most of us.

Underworld (1927). Josef von Sternberg’s gangland melodrama with George Bancroft and Clive Brook is often considered the first modern gangster film. I am intrigued that the film was produced while the real-life criminals the narrative was based on still ruled the streets. Underworld includes many standard conventions of the crime film, including  protagonist Bull Weed who is appealing despite committing heinous crimes, tough-talking gangster molls with colorful names who dress in the high fashion of the day, shootouts and getaway cars, and urban locales such as crowded speakeasies, seedy apartments, and dark dangerous streets. The film won the Best Original Story Award for writer Ben Hecht, who worked as a reporter for the Chicago Daily News in the 1920s during Al Capone’s heyday. Some of the characters are clearly patterned after real-life Chicago gangsters that Hecht had written about for the News—an extra treat for Chicago audiences. More recognizable to classic film fans is the resemblance between Underworld and Howard Hawks’s Scarface from 1932.

Roger Touhy, Gangster (1943). Touhy never had the national name recognition of Capone, but his story is known in Chicago because it involves several of the city’s notorious historical figures. During Prohibition, Touhy, who had grown up in Des Plaines, Illinois (where I teach at a local college), quickly rose from local thug to powerful bootlegger.  By 1933, Touhy had become a serious rival to Capone partly because he was protected by Chicago’s very corrupt, newly elected mayor Anthony “Ten percent Tony” Cermak—at least until the mayor was assassinated a few months later. Capone was able to get rid of his rival by arranging the fake kidnapping of white-collar criminal John Factor. Factor, who was the brother of Hollywood cosmetic manufacturer Max Factor, was ordered to accuse Touhy of the crime in exchange for favors that allowed him to avoid extradition. After two sensational trials, Touhy was convicted of kidnapping John Factor and sentenced to 99 years in prison.

The movie details Touhy’s rise from small-time hood to powerful bootlegger, then follows his troubles with rivals (Capone is never named in the story), who frame him for kidnapping. They arrange with crooked Chicago politicians for Touhy to serve a life-long term in Stateville prison. Desperate to be free again, Touhy plots to break out with buddy and cellmate Basil “the Owl” Banghart. Preston Foster stars as Touhy and is ably supported by Victor McLaglen, Anthony Quinn, Harry Morgan, and Moroni Olsen.

ROGER TOUHY (RIGHT) & HIS GANG DURING THE FACTOR TRIAL

The prison scenes were filmed at Stateville Prison in Joliet, Illinois, where the real-life Touhy had been incarcerated. The film previewed at Stateville on July 12, 1943, with Governor Dwight H. Green, about 1,000 police officers, and the state’s attorney in attendance. Touhy sued 20th Century Fox to prevent the film’s general release, but he was ultimately unsuccessful. Roger Touhy, Gangster opened the following summer.

Too bad no one ever followed up on Touhy’s story after 1944. In the mid-1950s, Touhy hired lawyer Robert Johnstone to get his case heard before federal judge John P. Barnes. Barnes declared that Touhy had been railroaded in a conspiracy between the mob and the state attorney’s office and that Factor had “kidnapped himself” to avoid extradition. Touhy had already cowritten his autobiography The Stolen Years with Chicago crime reporter, Ray Brennan, when he was finally released in 1959. John Factor, who was then a partner with mob types in the Stardust Casino in Vegas, sued Touhy, his publishers, and Ray Brennan, claiming the book damaged his reputation as a “leading citizen of Nevada.”  The teamsters, who had connections with the mob, refused to ship the book, and Chicago’s bookstore owners were warned by mobster Tony “Big Tuna” Accardo, in person, not to carry the book. Touhy and Johnstone threatened to countersue, which would have put Factor on the hot seat by exposing his connections to the Chicago Outfit. Thus, 25 days after his release from 25 years in prison, Roger Touhy was gunned down gangland-style on his sister’s front doorstep.

The Joker Is Wild (1957). This biopic starring Frank Sinatra as nightclub comic Joe E. Lewis is not a gangster film, but the first sequence captures the rousing atmosphere of the speakeasy scene in Prohibition-era Chicago. Lewis had been a singer at the Green Mill on the North Side, a club leased to Capone’s crony Machine Gun Jack McGurn. Shortly after Lewis left the Mill to sing at a club called The New Rendez-vous, his vocal chords were cut during an attack by thugs, reportedly under McGurn’s orders. Lewis turned to comedy in burlesque joints, eventually developing the standup style that dominates night clubs today. Sinatra, who helped Lewis get jobs in Vegas during the 1950s and 1960s, seems perfectly at home as this character in this milieu, though the names of the gangsters and the clubs were fictionalized for the movie.

THE REAL LEWIS AFTER HE WAS ATTACKED BY McGURN'S THUGS.

When Lewis lived in Chicago, he resided at the Commonwealth Hotel, which is just a couple of miles from where I live. The Green Mill (called the Green Mill Gardens in Lewis’s day) is also just a few blocks away. Also close by is the Holiday Club, where I meet my movie-club pals a couple of times a month to talk movies. The Holiday features a retro, 1950s look, which it comes by honestly because it hasn’t been renovated for decades. The backroom décor includes a poster from The Joker Is Wild, plus other Sinatra-related memorabilia. My proximity to the real-life history behind this biopic stirs the movie tourist inside me, so this film has become a personal favorite.

The Valachi Papers (1972). For years, my understanding of the Mafia was influenced by this film. Charles Bronson stars as informant Joseph Valachi, who was the first to reveal the history and the inner workings of the mob to federal agents. The film uses a flashback structure to relate Valachi’s career with the New York mob, which began at the tail end of Prohibition and continued into the 1960s. Bronson made a suitable Joe Valachi, who was a tough-looking “soldier” for such notorious gangsters as Salvator Maranzano and Lucky Luciano. Seeing the film years later, I was disappointed that it did not hold up to my memories of it. It lacked a believable recreation of the different historical eras, while the shift from one era to another seemed choppy.  I include it here because it opened my eyes to a part of urban history that is never taught in school.

CAGE (MIDDLE) PLAYS VINCENT DWYER, WHO WAS BASED ON MAD DOG COLL.

The Cotton Club (1984). Francis Coppola’s much-maligned combination of musical and gangster film is an underrated experiment in genre-busting that most reviewers just didn’t get. One of the many reasons I like the film is because of the gangster lore. The characters are mythic interpretations of famous mobsters, such as Cotton Club owner Owney Madden and bootlegger Dutch Schultz, or fictionalizations of real-life gangsters like Bumpy Rhoades, who was inspired by Harlem crime lord Bumpy Johnson. In this vein, Nicolas Cage costars as Vince Dwyer, a fictionalized depiction of crazed Irish enforcer Vincent “Mad Dog” Coll, who had been played by John Davis Chandler in the 1961 film that is showing on TCM this Wednesday. The Cotton Club gives a fair interpretation of the events that led to Coll’s murder at the hands of hitmen who may have been working for either Madden or Schultz, or both.

CHANDLER AS MAD DOG CALL

The montage sequence that serves as the movie’s climax intercuts Gregory Hines tap-dancing at the Cotton Club with gangsters annihilating each other on the streets, giving Hines’s routine a destructive, violent edge and the shoot-out a mythic, artistic underpinning. The seduction of violence is at the heart of the gangster genre, even in this experimental example by Coppola.

Eight Men Out (1988). John Sayles, respected veteran of indie filmmaking, directed this account of the 1919 Black Sox Scandal in which various team members for the Chicago White Sox threw the World Series for money. Despite a low budget, Sayles recreated the era with suitable nostalgia and atmosphere, and the film’s likable stars, including John Cusack, Charlie Sheen, and D.B. Sweeney could actually play baseball. Sayles turns the story into a parable about unfair labor practices that invite corruption and exploit naïve workers, who end up taking the fall for greedy, stingy owners and corrupt forces on the fringe of big business. The corrupt forces here take the form of white-collar gangster Arnold Rothstein, who rigged sports, manipulated stock prices, and lured financiers into his scams. Rothstein’s story is depicted in King of the Roaring 20s: The Story of Arnold Rothstein on TCM on Wednesday evening.

MICHAEL LERNER PLAYS ARNOLD ROTHSTEIN IN 'EIGHT MEN OUT.'

During the Jazz Age, when the majority of America seemed to be against Prohibition, consuming or buying illegal liquor created an atmosphere in which breaking the law or the rules became socially acceptable. This film depicts the way in which gangsters, mobsters, and crime bosses rubbed shoulders with businessmen, investors, celebrities, and even the average working man, making it easy to seduce and lure folks into going for the easy money. Many Chicagoans are fond of the film because writer and activist Studs Turkel appears alongside Sayles as sportswriters Hugh Fullerton and Ring Lardner, Jr., who serve as a kind of Greek chorus to the action.

Billy Bathgate (1991). Writer-director Robert Benton’s interpretation of E.L. Doctorow’s novel stars Dustin Hoffman as gangster Dutch Schultz, Bruce Willis as ill-fated hitman Bo Weinberg, and Nicole Kidman as rich girl Drew Preston. Loren Dean plays the title character, a teenager who is lured into the gangsters’ world. The film is about the seductive nature of the money, power, and glamour of the gangsters, as both Drew and Billy get caught up in the lifestyle before the hard-core violence that is also part of the life snaps them out of their reverie.

BRUCE WILLIS AS BO WEINBERG IN 'BILLY BATHGATE'

This film was ignored or forgotten almost immediately upon release, partly because Warren Beatty’s Bugsy overshadowed it and partly because its troubled production resulted in rumors that star Hoffman was dissatisfied with the final cut. However, the work of cinematographer Nestor Alemendros makes the movie worthwhile viewing.

Billy Bathgate makes a nice double feature with The Cotton Club, because it almost picks up where Coppola’s movie leaves off. Willis’s character, Bo Weinberg, was probably the killer who hit Mad Dog Coll for Schultz and Madden, but like most participants in the underground, he fell out of favor and was rubbed out in an even more frightening manner. Legend has it that his feet were planted in cement, and, after it hardened, he was thrown into the East River to drown.

I enjoyed researching the “Stars of Prohibition,” and I am thinking of flushing out the topic for another article. If anyone can think of other films loosely based on real-life Prohibition-era gangsters—especially lesser-known movies—please let me know.