There are few movie genres that are more beloved than that of the Gangster Genre. While it’s mostly gone the way of the Mafia itself in recent years, that doesn’t mean that there still aren’t multiple classic films that came out during the golden age of gangster movies (from the late 1970’s through the mid 1990’s). So, get ready to hear terms like “Based on a true story”/”Undercover Cop”, the names Pacino, Deniro, De Palma and Scorsese, and to perhaps have your idea on what constitutes a “Gangsters Movie” challenged!
15. King of New York
If there’s a film that has dominated 90’s era East Coast Hip Hop, it’s the Christopher Walken vehicle King of New York. The reason, outside of the perfect title for that era, is probably that this film is a lot more about the drug trade (namely the cocaine/crack trade) than most films in the gangster genre up until its release, which was a reflection of the Mafia’s resistance to selling drugs in it’s heyday. The Notorious BIG often referred to himself as Frank White, to the point that even his arch enemy, Tupac, referred to him as such in his famous diss track “Hit ‘Em Up” (or at least one of his underlings did). While this movie isn’t as well known as the others on the list it was the perfect film to coincide with the crack era of the 80’s and the devastated inner-city communities. It was also one of the better performances of Christopher Walkens career as well , and one of his last roles before he became a caricature of himself.
14. Gangs of New York
Some may not consider this film to be a gangster movie because of the era, but it’s obviously a movie about the early gangs that inhabited the New York neighborhood of the Five Points. This Martin Scorcese masterpiece shows that history does indeed repeat itself as “Real Americans”, lead by Bill the Butcher, essentially spit on the Irish Immigrants as they enter the United States at Ellis Island. The other half wants them for votes and to help fight in the Civil War, which showed again that not much has changed outside of the size of the buildings in New York. This movie is a much more personal story than most other Gangster films as Leonardo DiCaprio’s character, named Amsterdam, is struggling with the loss of his father and thinking about what revenge would mean for him, his friends, his enemy and his neighborhood. Many people thought that Director Martin Scorsese should’ve won the Oscar for Best Director for this film, but like his muse in this movie and many others, Leonardo DiCaprio, he was overlooked yet again. The recently retired Daniel Day Lewis wasn’t however, as his role as Bill the Butcher ended up being one of the most iconic in film history; because of that that this film earned its spot on this list.
13. The Untouchables
The Untouchables is the true(-ish) story of the “Untouchable” agents at the Treasury Department in early 1930’s Chicago and their attempt(s) to take down Al Capone despite the love that many in the city, including the Chicago Police Department, had for him. This film could’ve been ranked higher but it suffers from not having enough of Robert De Niro’s Capone, who is really only in the movie for a handful of scenes. The story goes that De Niro, ever the method actor, was even wearing the same type of silk underwear that Capone wore in real life. It’s that effort that makes it a pity that he was in the movie for maybe ten minutes, tops. Every scene with Capone shows why he was so beloved and so feared, as his charm oozes a certain type of lethality that shows that he could go from being the most lovable guy in the room to the most feared, in the blink of an eye. In one of the many memorable scenes from the film, Capone murders one of his own men at a round-table meeting using a baseball bat, without missing a beat in the business discussion with his men. This is also one of many films by Director Brian De Palma to make this list, as well.
12. American Gangster
Many of these films are based on true stories but few are as accurate as the story of Frank Lucas. This man almost single-handedly ran the heroin trade on the East Coast during the Vietnam War and ended up turning and helping put away many of the people he used to work with and against. The film follows Denzel Washington’s Lucas as he’s tracked down by Detective “Richie” Roberts, played by Russell Crowe. A common theme in all of these movies but especially depicted in American Gangster and the Untouchables, is just how prevalent police corruption was in the days where officers were getting paid more by organized crime than the city/state they worked for. At the beginning of American Gangster, we see Crowe turn in over a million dollars that he found; very few cops want to work with a guy who’s that honest. This was an important film as it showed how racism impeded the polices ability to capture Lucas himself, as they refused to believe that a black guy from Harlem could run such a major operation. It is because of that, that this film had an A-list cast and soundtrack (which was recorded as a full album by Jay-Z). Lucas, who was still alive, was able to consult on the film which gave it a gritty feel that helped distinguish it from other similar films.
11. A Bronx Tale
A Bronx Tale is the semi-autobiographical tale of one of it’s stars, Chazz Palminteri, who was discovered while performing his story as a one man show in Los Angeles by the eventual co-star and director of the film, Robert De Niro. In the movie, Palminteri plays Sonny, a mid-level boss in the Bronx during the 1950’s. This film is often overlooked when people discuss the great gangster films of the early 90’s, because of it’s smaller scope and more personal feel. It’s really the story of ‘C’, whose first name is Calogero, and the two father figures in his life: his actual father (a bus driver played by De Niro) and Sonny, who takes a liking to ‘C’ after he doesn’t finger him for a murder he witnessed at the age of nine. The film perfectly depicts a 1950’s Bronx and the racial strife that envelopes the neighborhood over one summer. And while a lot of the Mafia story-lines are more of a backdrop than anything else, it feels like a much needed character study that came out while gangster movies were coming out as often as comic book movies are these days.
While this wasn’t the first, or last, of Johnny Depp’s forays into the criminal underworld as an actor, it’s definitely one of his best. It’s yet another true story, this one being the life story of George Jung, who was so heavily involved in the cocaine trade at it’s outset that at one point there was about an 80% chance that the cocaine on the street in the early 80’s came from his cartel buddies (including Pablo Escobar). The film is a Scorcese-esque biography that ends on one of the most depressing notes in the history of film making. In a trend continued by Sharon Stone (higher on this list), Penelope Cruz is so unlikable in this movie that you actually dislike her as a person afterwards. The depressing ending makes you dislike Jung’s real life daughter, too. I mean, look at that face! Visit him! While these movies do get accused of glorifying a life of crime, it’s films like Blow that do such a great job of showing that crime doesn’t pay. In fact, it may be the biggest “Crime doesn’t pay” film on this list.
The only British entry on this list, Snatch is the crown jewel of Writer/Director and former husband of Madonna,Guy Ritchie’s, filmography crown. Starring Brad Pitt as a “pikie” bare knuckle boxer and Jason Statham, the film is a brilliantly interwoven story about the seedy underbelly of crime in the UK. While the film has more twists and turns than a street in London, it’s the performance of Brad Pitt, who speaks in a dialect that is extremely hard to understand (on purpose). It’s rare in these films to see the bad guys get their comeuppance because the real world doesn’t work that way and a lot of these are films based on reality. So it’s always nice to see a plan work out like it does so masterfully in Snatch (Which not surprisingly isn’t a true story).
8. Reservoir Dogs
Reservoir Dogs was the feature length debut of Writer-Director Quentin Tarantino, and what a debut it was! The film follows a group of career criminals and one undercover cop, as they deal with the aftermath of a failed diamond heist as they attempt to figure out what went wrong. The duration of the film has one of the most harrowing performances ever by Actor Tim Roth who is playing the undercover cop who was shot in the stomach and is slowly and agonizingly bleeding to death. This film also gave us one of the most demented scenes in Hollywood history in which Michael Madsen’s Mr. Blonde tortures another police officer by cutting off his ear while dancing to ‘Stuck in the Middle With You’. Talk about an introduction to Tarantino! While some consider his follow-up Pulp Fiction to be the superior gangster film, Pulp Fiction’s disjointed nature makes it more of a crime movie than a gangster one and while that was a landmark for cinema, it doesn’t make this list.
7. Donny Brasco
Donny Brasco is the true story of an undercover FBI Agent played by Johnny Depp, which was his first major foray into the gangster genre (but it wouldn’t be his last). Co-starring an extremely vulnerable Al Pacino as essentially the guy that Depp ends up taking advantage of, you really start to feel for Pacino’s character as the film goes on. It shows a side of the Mafia that hadn’t been seen before on film, where the criminal activity is depicted as really no different from any other job (outside of the murder, of course). Where people who put in a lot of work feel like they’re constantly being overlooked for promotions or feel like they always have to look over their shoulder for the next round of layoffs/murders. Having someone like Pacino in the role of an aging gangster was a great idea, as he had pretty much personified the genre alongside Robert De Niro for most of the decade(s) preceding this movie as well. This is one of the film’s that people refer to when they talk about the Depp that they like, being that he’s playing an actual human being as opposed to another crazy character. It’s the success of this film that will get Depp roles in the gangster genre for the rest of his life as well.
6. Carlito’s Way
Al Pacino has been in so many amazing gangster movies (and one terrible Adam Sandler film), that a movie as great as Carlito’s Way doesn’t even end up in his top two performances. Wow. Carlito’s Way follows Carlito Brigante after he is released from prison at his appeal hearing which was won by his crooked lawyer, who is played perfectly by Sean Penn. This role nabbed Penn a Golden Globe nomination. One of the things that makes Pacino great is the fact that he can play a Cuban a la Scarface, an Italian a la The Godfather or a Puerto Rican a la this film and he always brings something new to each gangster film he appears in. While it does check a lot of the gangster movie boxes, it also focuses on a love story; something that the genre rarely touches upon. The ending is one of the more amazing ones as well; it makes sure that you’ll never forget Benny Blanco from the Bronx.
Casino is perhaps the most overlooked De Niro/Scorsese collaboration (outside of perhaps The Comedian). Despite that though, it is a classic that is carried by three major performances from De Niro, Joe Pesci and Sharon Stone. Stone plays De Niro’s character’s wife and does such a great job that you actually dislike her as a person afterwards (much like Penelope Cruz higher up on this list). Another film that is loosely based on a real story , this film looks at the Mafia’s best bet ever, moving into Las Vegas in a way that no other film outside of Bugsy has. When all is said and done, Casino will stand tall as one of Scorcese’s masterpieces.
If King of New York represents 90’s East Coast rap, then Scarface represents rap from everywhere ever since then. Back in the days of MTV’s Cribs, you couldn’t find a (rented) mansion that didn’t have a Scarface poster, DVD or Blu-Ray. This may be Pacino’s most iconic role and is definitely Director Brian De Palma’s best work;it was only recently announced in an interview with Pacino and De Niro, that De Niro was up for the role of Tony Montana as well. While that would’ve been amazing to see, it’s impossible to picture anyone but Pacino screaming “SAY HELLO TO MY LITTLE FRIEND!” and that’s a testament to a master of his craft working at peak levels.
Between Goodfellas and The Departed it’s essentially a toss up as to which film is better, in that they’re both perfect films. Goodfellas has a bit of a let down when it comes to its ending, mainly because films that are based on reality don’t have cheery endings and because The Departed’s endings in one of the best in the history of cinema. What Scorsese does so well is to get you invested in characters that are essentially bad people, emotionally. So, despite the fact that Ray Liotta’s character is helping stop killers and thieves you can’t help but hate the guy and feel for the people you spent the whole movie getting to know as his/your family. That’s what’s Goodfellas is all about. And while it’s style and pacing has been copied by films even on this list, nothing beats the original.
2. The Departed
While Martin Scorsese shows up on this list more than any other director (with Brian De Palma a close second), it’s The Departed that is his Magnum Opus, and that’s really saying something. While some may consider it to be Goodfellas, the difference is that Goodfellas was so successful that it was copied over and over again (See: Blow), to the point that his movies almost became a genre in and of themselves. The Departed follows another undercover cop targeting the mob and is loosely based on the story of James “Whitey” Bulger the notorious Irish gangster from Boston who was still on the lam during the filming of this movie (which brought protests from people in Boston who were negatively effected by Bulger and his crew). This film is a who’s who of A-list actors from Leonardo DiCaprio, Matt Damon, Mark Wahlberg, to Alec Baldwin and Jack Nicholson. Being one of Nicholson’s last major roles, he does an amazing job as the leader of a gang that really doesn’t know any life outside of the mob. DiCaprio’s character, while undercover, begins to lose his identity and the film is really about that more than anything. Scorsese finally nabbed his first Oscar for Best Director for this film and it ended up sweeping Best Picture, Best Adapted Screenplay and best Editing as well. Mark Wahlberg was also nominated for Best Supporting Actor, which made little sense as he was essentially playing himself and considering that yet again (at the time) DiCaprio went without a nomination.
1. The Godfather Saga
Without this film, the rest of this list might not exist. And, while there are three separate films that comprise the Godfather Saga, it made sense to clump them together even if Godfather Part III brings their prestige down a little. There are few films that are as revered as the Godfather’s Part I and II, which are based on the books by Mario Puzo. The films are a who’s who of their own, with the legendary Marlon Brando, Robert Duvall, Diane Keaton and both Al Pacino and Robert Deniro starring in the second film (which serves as a flashback of sorts). During the production of the first film, it’s been reported that director Francis Ford Coppola nearly dropped out after the studio cast Brando as the Godfather. Ironically, despite Brando’s iconic career, it was this film that really did solidify him as the “best actor ever” (at that time). So, while this film has been dissected in every which way possible, one little known fact is that the actor that played Fredo Corleone, John Cazale, was only in a handful of films before he died from cancer at the age of 42 back in 1978. While he was never nominated himself, EVERY single movie he was featured in was nominated for Best Picture at the Academy Awards. I guess Fredo really is smart after all.