"As far back as I can remember, I always wanted to be a gangster." — Henry Hill, Goodfellas
Ask a random selection of Americans what they think about crime and criminals and you’ll probably get an earful about gun control, sentencing, the drug war, and so on. However, ask that same group of people what they think about gangsters and more than a few will probably reference Scarface, The Godfather, Goodfellas or some other fictionalized account of the predominantly Italian-American mobsters that make up La Cosa Nostra. Why the disparity? Why do we vilify petty thieves and drug addicts, but mythologize these career criminals and murderers?
The answer to that question is exceedingly complex, but it likely has to do with our fondness for those who are willing to publicly thumb their nose at "The Establishment." In much the same way the yellow journalists of the 19th century sensationalized the exploits of colorful outlaws like Jesse James and Billy the Kid and turned them into folk heroes, Hollywood has latched on to their 20th century equivalents in the mafia and made them theatrical heroes. Today, we have "gangster rap" and video games like Grand Theft Auto, where kids can go on violent crime sprees from the comfort of their own home. In the docu-series Gangsters: America's Most Evil, making its REELZ debut October 3rd at 9p ET/6p PT, we will be exploring the rise and fall of some of the most deadly outlaws ever brought to justice, but let's first take a look at some of the movies about real-life notorious gangsters that have helped to take these denizens of the underworld and transform them into popular icons. Be advised, some of the videos below are NSFW.The rise and fall of the deadliest kingpins
Robert De Niro as Al CaponeThe Untouchables (1987)
Brian De Palma's account of Eliot Ness' takedown of the Chicago crime boss was based on the G-Man's own autobiography of the same name (ghostwritten by Oscar Fraley) published in 1957. It chronicles how every effort to put Capone behind bars for his bootlegging, bribing and murdering ways ultimately failed until an accountant who though outside of the box realized that the mob boss hadn't paid taxes for years and could be tried for tax evasion.
Ray Liotta as Henry HillGoodfellas (1990)
Martin Scorsese's 1990 crime drama was adapted from Nicholas Pileggi's 1986 non-fiction book Wiseguy about the rise and fall of Henry Hill, who became connected with the Lucchese crime family, but ultimately descended into drugs and and got pinched by the feds. Hill turned confidential informant for the FBI, becoming "an average nobody...a schnook" and disappeared into anonymity as a member of the Witness Protection Program.
Daniel Day-Lewis as Bill the ButcherGangs of New York (2002)
Scorsese makes our list again, this time tackling real-life gangsters of the 19th century. Inspired by Herbert Asbury's 1928 non-fiction book of the same name, the movie follows Amsterdam Vallon (Leonardo DiCaprio) on his quest for revenge against the man who killed his father, New York crime boss Bill "The Butcher" Cutting, against the backdrop of the 1863 New York Draft Riots.
Denzel Washington as Frank Lucas
American Gangster (2007)
Ridley Scott's period gangster drama was based upon a New York magazine story about a Harlem limo driver who rose to become the largest supplier of heroin in New York City in the early '70s by cutting out the middle-men and importing the drug directly from Thailand. Smart, fearless, and disciplined, Lucas managed to fly under the radar until an ambitious detective (Russell Crowe) noticed him sporting a bit too much bling at the Joe Frazier-Muhammad Ali title fight and decided to investigate him.
Sean Penn as Mickey Cohen
Gangster Squad (2013)
Ruben Fleischer's movie may have been a work of fiction, but the LAPD's "Gangster Squad" was a real-life crime-fighting unit put together to catch Meyer "Mickey" Cohen, the Brooklyn-born former boxer-turned-enforcer-turned-kingpin who helped set up the Flamingo Hotel and became one of the most notorious criminals in California.
Cliff Curtis as Pablo EscobarBlow (2001)
Ted Demme's adaptation of Bruce Porter's non-fiction book Blow: How a Small-Town Boy Made 100 Million with the Medellín Cocaine Cartel & Lost It All focuses on the rise and fall of George Jung (Johnny Depp), who makes a fortune smuggling cocaine for Colombian kingpin Pablo Escobar, but ultimately loses his wealth, his freedom and his family.