Weekend Roundtable: Favorite Gangster Movies

In honor of the FBI’s extremely belated capture of notorious Boston mobster James “Whitey” Bulger, who’d been a fugitive for 16 years (12 of them on the Ten Most Wanted list), this week’s Roundtable topic seemed like a gimme. We’re of course going to list off our favorite mob or gangster movies. What are yours?

Before we get to this, there’s just one catch. When I sent out the instructions to the staff, I had to take ‘The Godfather‘ (any of them) and ‘Goodfellas‘ off the table. I’m sorry, but those are just too easy. We’re going to stipulate that those movies automatically fall on everyone’s list of favorites. With those exclusions, let’s see what everyone came up with.

Luke Hickman

I never really cared much for the gangster genre until ‘The Departed‘. Martin Scorsese had definitely made plenty of Best Picture-worthy films prior to it, but ‘The Departed’ was truly deserving of finally awarding him the Oscar. There isn’t a single flaw with it! It’s constantly pitch-perfect.

Most gangster films are usually set in a different time period or, if set in present day, follow thugs in street gangs. Set in our time and inspired by true organized crime boss Whitey Bulger, ‘The Departed’ is easier to connect with because it isn’t a soft focus story of the past. The huge cast brings a whole lot of life into it. Considering that the cast is chock full of well-known actors, you’d figure that they’d try to constantly outshine one another, but the opposite happens. Each actor gives the performance of a lifetime. Full of unpredictable twists and turns, unless already you’ve seen the original Chinese film that it’s based on (‘Infernal Affairs’), you’ll have absolutely no idea where ‘The Departed’ is going. It’s literally and figuratively mind-blowing. The editing is fresh, creative, fast-paced and totally insane. Without a doubt, ‘The Departed’ is the best gangster film made in my lifetime.

M. Enois Duarte

One of the very best gangster films ever made, and a long-time personal favorite of mine, is without a doubt Brian De Palma’s ‘Scarface‘. Largely panned by critics and engulfed in a tidal wave of controversy, the movie was a moderate success at the box-office by today’s standards (budgeted at $25 million, which comes to $54 million nowadays, it grossed approximately $45 million, which would be around $97 million today). But with time, the Al Pacino crime drama grew in popularity and eventually became a cultural phenomenon – practically revered as the icon of true thug life. Based on the 1932 Howard Hawks movie and updated by Oliver Stone, ‘Scarface’ is a no-holds-barred, brutally violent film that explores the dark side of the American dream. Powerful, compelling, shocking, spellbinding, whatever generic accolade one can think of, this movie has it all and easily ranks as one of the top ten must-watch cult films of all time. Can you tell that I really love this movie?

Aaron Peck

I love learning about the history of Las Vegas. I’ve got books and books on the subject. Why? I don’t really know. All I know is that it’s a city that’s had a very tumultuous past, mostly because the Mob was so involved when Las Vegas was getting established. Nowadays, most of the casinos down there are run by ultra-rich billionaires, but back in the day, Las Vegas was the Mafia’s turf. No movie exemplifies the stranglehold the Mafia had on Vegas more than Martin Scorsese’s ‘Casino‘. Coming off the success of ‘Goodfellas’, Scorsese put together another great gangster film starring ‘Goodfellas’ alums Robert De Niro and Joe Pesci.

What I love most about ‘Casino’ is that it’s as much a history lesson about how Las Vegas came to be (as we know it today) as it is a gangster movie. We follow Sam (De Niro) around during the movie as he works at the Mafia-controlled Tanigers casino. We see the height of Mafia power in Vegas, and then its eventual crumbling. The movie ends with the old Las Vegas being demolished to make way for a more family-friendly version. Scorsese captures the transformation of Sin City perfectly. It’s a great film.

Mrs. Z

Personally, I prefer my gangsters with British accents. Before he was Bond, Daniel Craig played the charming unnamed drug dealer (let’s call him Mr. X) in Matthew Vaughn’s stylish crime thriller ‘Layer Cake‘. Mr. X just wants to retire in peace but, as is often the case with gangsters, every time he tries to get out, they pull him back in.

‘Layer Cake’ moves at a brisk pace, taking a few detours along the way to keep things interesting. The film is sprinkled with touches of dry black humor and some intense violence. In fact, it’s the only gangster movie I’m aware of where tea is used as a weapon in brutal beating. The supporting cast is chock full of classic British character actors including ‘Star Trek’ vet Colm Meaney, ‘Bronson’ star Tom Hardy, and ‘Harry Potter’ alums George Harris and Michael Gambon (in a role that’s about as far from Dumbledore as you can get). Even Owen Harper from ‘Torchwood’ makes an appearance.

The film gets bonus points for the soundtrack, particularly its interesting use of the Duran Duran classic “Ordinary World.” And, if you’re in need of a good drinking game, IMDb trivia notes that the film uses the F-word and its deriviatives 201 times. For some reason, it just sounds classier with the accent.

Mike Attebery

It’s been too long since I’ve watched this one, but just checking out the trailer again had me rolling. Though few would consider it a typical gangster movie, ‘Broadway Danny Rose‘ is the best “Family” comedy that I can think of. The film also features one of Woody Allen’s best performances.

Mob movies always talk about loyalty and standing by “The Family.” Well, theatrical manager Broadway Danny Rose has to be the most loyal guy in the business. Despite representing acts like a blind xylophonist, a one-legged tap dancer, a stuttering ventriloquist and a one-armed juggler, Danny has absolute loyalty to his clients. Hell, he even has the cast of misfits over to his home for the holidays because he knows they, like him, have nowhere else to go. They are his family.

Blindly faithful guy that he is, Danny also knows when he can’t afford to lose an act with potential. So when his single promising client, a lounge singer named Lou Canova, asks Danny to help him bring his mistress, Tina Vitale (Mia Farrow) to his concerts, Danny agrees. Unfortunately, when Tina’s jealous mobster husband mistakes Danny for his wife’s lover, two gangsters are quickly sent after the hapless talent manager to teach him a lesson of the leg-breaking variety. This movie is chockablock with quotable dialogue, hilarious scenes, and memorable characters. With the perfect balance of humor and heart, it’s a gangster movie that I think you’ll find surprisingly touching.

Josh Zyber

I have to go with the Coen brothers’ early masterpiece ‘Miller’s Crossing‘, which I would still hold as their best film to date. Not only does the movie have a fabulous cast (including the likes of Gabriel Byrne, Albert Finney and John Turturro), stylish direction, countless homages to classic gangster films, and just the right measure of patented Coens’ humor, it’s also their most perfectly written and plotted film. There’s not a single scene, action, or line of dialogue that isn’t absolutely essential. And that devastating climax… It’s a thing of beauty. “Look into your heart! Look into your heart!”

I also want to throw out some honorable mentions: ‘A Better Tomorrow’, ‘Bugsy’, ‘Carlito’s Way’, ‘City of God’, ‘Dick Tracy’, ‘Eastern Promises’, the ‘Infernal Affairs’ trilogy, ‘The Krays’, ‘Lock, Stock & Two Smoking Barrels’, and ‘The Untouchables’.

Tell us your favorite gangster movies in the Comments.


  1. javier

    Menace II Society
    ” he was America’s nightmare…..young, black, and didn’t give a fuck”

  2. Jane Morgan

    It’s not full-on gangsta, but I’d kick in ‘Kill Bill, Vol 1.’

    O-Ren Ishii is practically the whole movie.

  3. Ruben

    Road To Perdition
    I’m usually not a big fan of father and son stories, but Road To Perdition is so brilliantly acted and touching, though still kind of Badass (shootout in the rain-scene).
    It’s also my favourite Mendes-movie.

  4. since godfather and goodfelas are out im going a bit diffrent and go with innocent blood. i love the combo of mobsters and vampires. a great cameo by frank oz and sam rami.

  5. Michael E Kinane

    1)Once Upon A Time In America
    2) Millers Crossing
    3) Road To Perdition
    4) Bonnie & Clyde
    5) Kill the Irishman

  6. BostonMA

    well, i would choose Goodfellas at 1 and The Godfather at 1A but it is a good decision to exempt those from the listing so i guess i would have to pick Jean-Pierre Melville’s highly existential, morally ambiguous, career-best LE CERCLE ROUGE as my #1 pick for this thread, which could also fall in the genres of Crime or Heist as well, but due to it’s heavy influence of American gangster films that Melville loved so much, i think it’s fine to label it as such.

    The Departed would follow secondly with Pulp Fiction, The Godfather Part II, Rififi (similar circumstances to Melville’s masterpiece), Casino, White Heat, and Key Largo falling in the high up, honorable mentions.

  7. EM

    As a genre, gangster movies don’t much interest me. I guess it’s at least in part because I don’t find real-life gangsterism particularly interesting either. My tastes tend to lie elsewhere. Do Toy Story 3 and Time Bandits qualify as gangster movies?

    If not, perhaps we can go with Howard Hawks’ classic film noir The Big Sleep, which follows Humphrey Bogart as Philip Marlowe, a PI
    who becomes embroiled in a rather convoluted case involving numerous criminals, including gangsters. The pacing crackles; some complain that the plot can be hard to follow (I recommend watching it a couple of times in a row), but crisp dialogue and excellent performances help smooth over those bumps.

    Perhaps a more conventional gangster film would be Wallace Worsley’s 1920 silent melodrama The Penalty, whose central character Blizzard, played by Lon Chaney (Sr.), underwent an unnecessary amputation of both legs as a boy and has become a twisted homunculus of a crime lord seeking vengeance on the doctor responsible, via the doctor’s daughter. In contrast with The Big Sleep, The Penalty’s plot is underdeveloped, but still the movie makes for great, slightly grand-guignolesque fun.

  8. Unleashed. it is, at its core, a gangster flick, a story about life inside the system for those who know nothing else, the thankless lacky position who doesn’t even understand what he’s doing, and his first break into a real life, while his previous one comes to beckon him. when ol’ Bob Hoskins loses his dog (i so wish the film were titled Danny the Dog here, as it is elsewhere in the world), he loses his muscle, and suddenly the pyramid has no base, and he gets the shit kicked out of him. i don’t know what blind people and pianos have to do with the mob, but maybe that’s an analogy for the outside world, playing high class, focusing on the microcosm that is their existence, oblivious of the other kind of family until it comes crashing into their living rooms…and into their hearts (sorry, bad trailer guy moment!).

  9. Sean

    Departed, Godfather, Goodfellas…all awesome, but don’t let the lack of good HD transfers fool you. The classics are every bit their equals and more.

    Check out The Public Enemy (1931)…Cagney is awesome, and the grapefruit scene rivals the most memorable scenes in any of the movies I mention above. Utter classic for a reason.

    Angels with Dirty Faces (1938) has the best ending of ANY gangster movie. And you get Bogey and Cagney.

    The original Scarface? Every time I see it I wonder why Lumet felt the need to remake it.

    And a second vote for White Heat. Never think you can’t portray sadism in the Hays censorship era. Another Cagney.

  10. You know… I don’t think I can honestly say there’s a single gangster movie I care for. Maybe one or two that I don’t dislike, at best. Unless Key Largo counts? 😉

  11. “The Departed” was the first Scorsese I ever saw (for shame, yes) and I thoroughly enjoyed it. It may be a stretch, but if we consider “gangster movies” to be a genre where “guys do something that the law doesn’t like”, then I’d consider “Ocean’s Eleven” (the remake). It’s so snappy, fun and fancy-free, I always feel good when I see it. It may be a “feelgood gangster film”.

    Is “The Usual Suspects” a gangster movie? Because that’s an awesome flick as well …

    • BostonMA

      “guys do something that the law doesn’t like” doesn’t make a Gangster movie at all. it’s more along the lines of having GANGSTERS in the movie, like Edward G. Robinson in Key Largo and Vito Corleone in The Godfather.

      Ocean’s Eleven is strictly a Heist film.

      • My bad! I haven’t seen that many gangster movies, then. “The Godfather” and “Goodfellas”, yes, but those are ‘too easy’ (as Josh said).

  12. I like British gangster films like Layer Cake and Snatch because they always include a heavy dose of what the overly-cynical American gangster pictures lack: Humor.

    And I don’t mean a few bits of it here and there, but a steady thread of dark humor throughout. Oh, and Rock-n-Rolla is severely underrated.

    • EM

      That reminds me of a movie I should have thought of earlier: The Ladykillers (I’m talking about the British original, of course). Now that movie is hilarious.

  13. I don’t mind when Gangsters are not the main/heroic characters. (E.g. Untouchables/Key Largo) They’re the villains to be stopped. But I get tired of gangster films where we’re supposed to follow some brutal murdering scum as the lead characters, and actually give a crap what happens over the length of the film?

    I actually have to at least reasonably like a main character to care what happens to them over the course of a film, otherwise it’s just pointless stuff happening on screen in which I couldn’t care less about the outcome.

    I’m in the UK, and I HATE British gangster films especially. They’re so forced, and try so hard to be ‘cool’ with the sepia tinted grunge and “oh look, we swear in cockney accents! Isn’t it amazing!”. I remember a guy from uni lending me Lock Stock to watch because it was ‘so brilliant’. Wish I could get those few hours back lol!

  14. Alex

    Absolutely love “The Untouchables”. Every time I walk through the Great Hall in Chicago’s Union Station, I think of that marvelous gunfight. It’s also delightful that Sean Connery can always be Sean Connery in spite of the nationality of the character and it still works. (He’s supposed to be Irish in “The Untouchables”, but I submit “Red October” as another example)

    “He pulls a knife, you pull a gun. He sends one of yours to the hospital, you send one of his to the morgue. That’s the Chicago way!”