True crime has been all the rage in Hollywood for a lot longer than it seems. In fact, telling stories about real-life criminals goes back to the very beginnings of film. Over the years some of our favorite movies, from The Untouchables to Goodfellas and more have told the (somewhat) true events of some very famous criminals' lives. Here is our list of some of our favorite movies about real-life mobsters and bad guys.
Al Capone - The Untouchables
Robert De Niro famously gained a bunch of weight to play legendary Chicago mob boss Al Capone in The Untouchables. Though the story is really about Eliot Ness (Kevin Costner) and the crew that took down Capone in the 1930s, De Niro stole the show with his amazing performance and he was rewarded with an Oscar for it. There's a reason it's considered one of the best gangster movies of all time.
Jimmy Conway - Goodfellas
There is no doubt that Goodfellas had to feature prominently on this list. Almost every character in the movie is based on a real mobster and, of course, the great Robert De Niro puts in another all-time great performance in this one as Jimmy Conway, who was based on the real-life gangster Jimmy "The Gent" Burke.
Jimmy Hoffa - The Irishman
Al Pacino sure knows how to play a mobster. Of course, at the top of any list is the fictional Michael Corleone in the Godfather movies, but he also has played some famous real-life criminals, like notorious union boss Jimmy Hoffa in The Irishman. Though his performance is, predictably, a little over the top, it's still the best in the movie.
Frank Lucas - American Gangster
Gangster Frank Lucas was a kingpin in New York City in the 1970s who revolutionized the drug trade in the U.S., specifically in Harlem. He spent years in prison for his crimes, but he's gone down as a legendary criminal since. In American Gangster he's played brilliantly by the great Denzel Washington as one of the best gangsters in film history.
Frank Costello - The Departed
It's easy to make fun of Jack Nicholson's sketchy Boston accent in The Departed, but what he nails in the role is the intensity of Whitey Bulger, who his character, Frank Costello, is loosely based on. While the movie isn't a true story, per se, many of the characters were based on real-life cops and robbers, including Costello. Like Bulger Costello is terrifying.
Lefty Ruggiero - Donnie Brasco
Lefty Ruggiero has gone down as one of the most notorious gangsters for what he did wrong - namely bringing the undercover police officer Joseph D. Pistone, better known as Donnie Brasco, into the Bonanno crime family. In the movie Donnie Brasco, Al Pacino plays the luckless Ruggiero wonderfully as a mobster who tries his best, but never really has things go his way.
Bugsy Siegel - Bugsy
Gangster Ben "Bugsy" Seigel left his mark on the world by basically inventing modern Las Vegas in the 1940s when he built the first hotel on what would become the famous Las Vegas strip. The movie Bugsy tells the story of Siegel and that hotel, The Flamingo with the great Warren Beatty in the title role.
John Dillinger - Public Enemies
During The Great Depression, the public was fascinated by criminals, gangsters, and mobsters. John Dillinger was at the top of the list of bank robbers that people just loved to follow the exploits of. Public Enemies covers quite of few of the famous criminals in Dillingers various gangs, and Dillinger himself is played wonderfully by Johnny Depp.
Ace Rothstein - Casino
Martin Scorsese's Casino is all based on real-life gangsters who moved out to Las Vegas to oversee the mob's investments in the city at the height of their influence in the 1970s. Sam "Ace" Rothstein, played by Robert De Niro, is based on Frank "Ace" Rosenthal, who was a legendary bookmaker and casino exec for the East Coast families.
Whitey Bulger - Black Mass
Whitey Bulger is one of the most infamous mob bosses in American history. Bulger ran the Winter Hill Gang in Boston for years before disappearing for decades after it got out that he was an FBI informant. Johnny Depp, who plays Bulger in Black Mass disappears into the role, playing it with the same smoldering intensity that the real-life Bulger was famous for.
Baby Face Nelson - O Brother Where Are Thou?
George "Baby Face" Nelson was a Depression-era gangster who gained popularity in the public eye for his brazen crimes and psychotic behavior. A heavily fictionalized version of Nelson features prominently in a couple of scenes in the Coen Brothers' classic O Brother Where Art Thou? played by Michael Badalucco.
Henry Hill - Goodfellas
This list absolutely has to include Henry Hill, played by Ray Liotta, in Goodfellas. Not only is the Scorsese classic among the best mob movies ever made (with an amazing soundtrack), but Hill made himself into a celebrity as a result of the movie and his many appearances on The Howard Stern Show before his death in 2012.
Lucky Luciano - Mobsters
1991's Mobsters was a star-studded movie with a big budget that flopped pretty hard. It also failed to inspire critics. It did, however, have some pretty memorable portrayals of famous gangsters from the early days of organized crime in America. One of the most important figures in that history, Charles "Lucky" Luciano, is played by Christian Slater in the movie, and if we're honest, he's pretty good, despite the movie's failings.
Anthony Spilotro - Casino
Anthony Spilotro, who was the basis for the character Nicky Santoro played by Joe Pesci in Casino was pretty much exactly like Pesci played in the movie, according to most accounts. That's amazing to think about as the character seems so over the top it's hard to believe.
Tony Montana - Scarface
We just had to include Tony Montana in Scarface on this list, but calling the character based on a real-life gangster is a little tricky. Montana, played by Al Pacino, is a Cuban refugee in the movie, whereas the character was very loosely based on the real Scarface, Al Capone. It's not exactly the most direct analog, but it does follow the gangster in his rise to the top of the drug trade in Miami, much like Capone and booze in Chicago. So... sort of?
Frank Sheeran - The Irishman
Frank Sheeran is one of the most infamous mob hitmen of all time. He is also the titular Irishman in Netflix's The Irishman. He worked for Jimmy Hoffa, and, at least according to the movie, assassinated the union leader at the behest of mobster Russell Bufalino.
Nicky Barnes - American Gangster
American Gangster was mostly about the rise and fall of Frank Lucas in Harlem in the 1970s, but his biggest rival at the time, Nicky Barnes, played by Cuba Gooding, Jr., also features prominently in the film. As portrayed in the movie, Barnes ran "The Council" and worked alongside the Italian mob families at the time.
Sonny Black - Donnie Brasco
Michael Madsen plays the character Sonny Black in Donnie Brasco who was based on the real-life mobster Dominick "Sonny Black" Napolitano. Napolitano was the leader of the crew, which included Lefty Ruggiero (Al Pacino in the movie). In real life, as in the movie, Napolitano trusted Brasco and ultimately was assassinated for that trust in 1981 when it was revealed that Brasco was really undercover agent Joe Pistone.
Frank Nitti - The Untouchables
To be clear, very little about the fictional Frank Nitti in The Untouchables is anything like the real-life Nitti. But, Frank Nitti was an infamous enforcer for Al Capone in the 1920s and '30s. In the movie, he has one of the most haunting mob deaths of all time, though it's completely fictional, as the real Nitti wasn't thrown off a building by Eliot Ness, but died many years later from a self-inflicted gunshot.
Mickey Cohen - Gangster Squad
One of the most important figures in the establishment of a mob influence on the West Coast and in LA and Las Vegas particularly was Mickey Cohen. Not only was he really the first "boss" in LA, but he also worked with Bugsy Siegel in the establishment of Las Vegas as a mob-run town in the early days. In Gangster Squad, a movie about the LAPD's case against Cohen, he is played wonderfully by Sean Penn.
Thomas DeSimone - Goodfellas
Tommy Devite, played by Joe Pesci in Goodfellas is one of the most unhinged mobsters ever portrayed on film. The character is based on the real-life Thomas DeSimone, who is part of the crew that Henry Hill is associated with. Some of the things that are likely true in the movie are his brutal murder of "Billy Batts" Bentvena, and his death at what he thought was going to be the ceremony to induct him as a "made man" as portrayed in the movie.
John Patrick Looney - Road To Perdition
Road to Perdition is a great example of a movie based on a graphic novel that isn't about a superhero, and it's loosely based on the life of Irish mobster John Patrick Looney. John Rooney, played by Paul Newman, was one of the most influential gangsters in northern Illinois in the early 20th Century.
Jimmy Hoffa - Hoffa
Decades before Al Pacino played the infamous union boss Jimmy Hoffa in The Irishman, another all-time great, Jack Nicholson, played him in Hoffa. The biographical film about Hoffa was a box office bomb when it was released in 1992 co-stars (and was directed by) Danny DeVito, and while Nicholson's performance wasn't loved by all the critics, he was earned a Golden Globe nomination for Best Actor.
Pretty Boy Floyd - Public Enemies
Director Michael Mann's 2009 hit Public Enemies has a whole bunch of characters based on real people on both sides of the law. One of those notorious bad guys was Pretty Boy Floyd who wasn't part of the gang led by John Dillinger but was tracked by the same G-man, Melvin Purvis (Christian Bale in the movie). Pretty Boy Floyd was played, appropriately, by Channing Tatum.
John Gotti - Gotti
One of the most ridiculed gangster movies of all time has to be Gotti. It's hard to recommend it as something to be watched and enjoyed, we couldn't leave it - or the performance by John Travolta as the infamous mob leader John Gotti - off this list. It's all just so... silly.
Russell Bufalino - The Irishman
Russell Bufalino, played by Joe Pesci in The Irishman, was the boss of his own family in Northeastern Pennsylvania. He was closely associated with the Five Families in New York City, and his cousin, William Bufalino, was Jimmy Hoffa's lawyer.
John Dillinger - Dillinger
One thing you really have to love about Tom Hardy is that he's pretty fearless in the roles he takes on and never plays it safe. In Capone, the English actor takes on the role of legendary Chicago mobster Al Capone. It's all about the end of Capone's life, after he'd been in jail for years and had lost his spot at the top of the Chicago outfit. It's a weird movie, to be sure, but Hardy is great.
Paul Vario - Goodfellas
Paul Sorvino plays the character Paul Cicero, based on Paul Vario in Goodfellas. That's a lot of Pauls! First name aside, Paul Vario was the caporegime in the Lucchese crime family who was put in jail in part on the testimony of Henry Hill (played by Ray Liotta in the movie). Sorvino was one of the most memorable parts in a very memorable movie as the quiet, but powerful, boss of the crew Hill was a part of.
Kevin Weeks - Black Mass
Jesse Plemons' portrayal of Kevin Weeks, an associate and enforcer with the Winter Hill Gang in Black Mass is one of the best performances in a movie filled with great performances. Alongside Whitey Bulger, Weeks was a brutal henchman who eventually turned against the mob and became a snitch, snitching on his boss, which is pretty ironic.
Baby Face Nelson - Public Enemies
Unlike the version of Baby Face Nelson in O Brother Where Art Thou?, the version played by Stephen Graham in Public Enemies is much closer to the real gangster. He's psycho, but he's pleasant. It's the perfect role of Graham and the performance is a real highlight of the film.
Al Capone - Capone
You really have to appreciate Tom Hardy's choice of roles. He rarely takes the easy ones. Instead he challenges himself, like playing the aging Al Capone in Capone. The film is all about the end of Capone's life, after he's served his prison time and lost his spot at the top of the Chicago outfit. It's a powerful man in completely decline mentally and physically. It's really a fantastic performance in an uneven movie.
Billy Batts - Goodfellas
William "Billy Batts" Bentvena, played by the great Frank Vincent (who is a master at playing mobsters) in Goodfellas is really only in one scene in the whole movie, but it's become such an iconic moment, when Nicky (Joe Pesci) stabs him to death with pen, that we had to include the real-life gangster on this list.
