Pick Six: The Six Best Outlaws in the Movies

In honor of my recent return to the magnificent Western Red Dead Redemption (Xbox loyalist converting to PS3, and the consequent trophy hunting syndrome, anyone?), I decided to set my sights on a fun-to-wrangle question – who are the six best outlaws in film? It’s true, I think, that villains tend to be more interesting than heroes, and outlaws tend to be more interesting than anyone, since outlaws aren’t necessarily always villains. It got me thinking – what makes a good outlaw? Is it the gadgets, the gear, or the movies they tear around in? I think I have an idea. The best outlaws are the kind we end up wanting to root for. I’ve included in my list my favorite quotes from these memorable outlaws and their associates, though where in the film they utter such lines I leave for you to remember – or discover – on your own.

Jesse James
Brad Pitt, The Assassination of Jesse James by the Coward Robert Ford

This is an odd movie. Enigmatic, maybe. I’m not sure. It’s definitely beautiful, definitely elusive, and it’s definitely one of Brad Pitt’s more memorable roles, all the more so simply because he hardly says a word through the entire duration of the film. I admit, the first time I watched this I didn’t much care for it – I think I might have been in the wrong place in life, or maybe I was just distracted, I honestly couldn’t tell you. What I can tell you is that upon revisiting it, I came to love it for what it was. Half myth, half faux-documentary, The Assassination’s Jesse James is reticent, brutal and beautiful. He’s a grounded, walking interpretation of the American legend, as compelling as he is unimpressive. I think the film’s greatest achievement is demystifying the mythic, while leaving the myth intact after the film draws to its highly unusual and conflicting end. This film is definitely worth a look.

Don’t that picture look dusty?”

Ben Wade
Russell Crowe, 3:10 to Yuma

3:10 to Yuma is an interesting film. It didn’t garner much of a following when it came out, and it hasn’t gained much traction in the time since, but I maintained then and I maintain now that this is everything a Western should be. Much like the ill-fated Cowboys and Aliens (another film I loved that nobody else seemed to like), 3:10 to Yuma is as indebted to the Western genre as it is to the actors and director that bring it to the screen. This is a case of remake-done-well, where the remake of a movie is better than the original. Gunplay, marital tension, father-son struggle and stark landscapes combine to make one hell of a film. Most importantly, 3:10 boasts a towering outlaw that we begrudgingly admire – we’re not supposed to like this man, his outfit is lean and nasty and his violence is unpredictable and vicious, but we can’t help but be drawn to his charisma, his sensitivity, his cursed pistol, and the fact that he can talk a woman out of her knickers before tea time. Played masterfully by the as-of-late-sadly-underwhelming Russell Crowe, Ben Wade is the best outlaw in the old West.

“Even bad men love their mamas.”

John Dillinger
Johnny Depp, Public Enemies

It’s a not-so-well-kept secret that I have a fascination/love affair/man-crush with/on John Dillinger, real life style, and so when Public Enemies hit theaters I was absolutely ecstatic. For those who don’t know, Dillinger was a real life crook, the last of the so-called “noble criminals” who gave way to the Baby Face Nelson’s and Al Capone’s of the world. There was nothing noble about a man like John Dillinger – he was brutal and crooked and selfish, but he was good at what he did, and he did it with a charisma, style and sense of principle that most criminals could only dream of. In short, he was a classy crook, and Michael Mann’s Public Enemies did him justice. I was also incredibly pleased with Depp’s portrayal of Dillinger, since he as an actor has fallen harder and harder from grace as of late for portraying the same exact zany variation of himself in the same exact Tim Burton movie released under a hundred different names. It’s strange, sometimes, to remember that Depp can actually act, and that when he does he can be a lot of fun to watch. Here, he portrays a man straight out of American lore, opposite a comparatively lazy performance by Christian Bale. See this movie for the history of it, for the great firefights, and the top notch acting. Do your best to ignore the filter that makes it look like it was filmed with a phone.

“What’s the score?”

Captain Jack Sparrow
Johnny Depp, Pirates of the Caribbean: The Curse of the Black Pearl

Okay. Let’s just say it. The Pirates of the Caribbean series went to hell in a handbag, but before it went off the rails it was actually really cool. Remember when the Curse of the Black Pearl first hit theaters, and we all went to it a hundred times and wanted to be pirates all over again? Remember the first time we saw that gold glittering under the water, or realized everyone on the boat was undead, or learned the monkey’s name was Jack? I’m of the opinion that the whole reason we had any such thoughts can be traced to the unforgettable Captain Jack Sparrow, a character brilliantly brought to life by Johnny Depp, and brilliantly massacred by Disney shareholders in later movies. He’s crafty, clever, hysterical, sexy and drunk most of the time – basically everything a pirate should be. Before this series got shot to shit, it used to be a lot of fun. “But why is the rum gone?” Jack sadly asks. I don’t know, I reply. Why is the rum always gone?

“And then they made me their chief.”

The Cats
The Cats, No Country For Old Men

There’s a scene towards the end of No Country for Old Men wherein Sheriff Ed Tom Bell, masterfully played by Tommy Lee Jones, inquires after the amount of cats his old uncle Ellis has roaming around his house. “Cats?” Ellis replies. “Several. Well, depends what you mean by ‘got. Some are half-wild, and some are just…outlaws.” I guess I cheated with this one, but only just. The entire film No Country For Old Men is made up of outlaws – there’s not an honest man among the cast of characters, except of course Ed Tom Bell himself, who looks on with a tired sense of defeat as the violence unfolds around him with all the gloomy disposition of a bruised black rose. I reserve this slot, therefore, for the outlaw cats that circle Ellis’ place, out in the Texas flats, yowling at the sun, and for this masterpiece of a film that they inhabit. (This film is, for those unaware, based on a Cormac McCarthy novel of the same name, and is a must see on many, many levels.)

“And then I woke up.”

Christian Bale, The Dark Knight Trilogy

There’s a strange delineation between outlaws and vigilantes. I think it’s because all vigilantes are outlaws, but not all outlaws are vigilantes. Batman, known in modern terms as the Dark Knight, falls pretty comfortably into both of these categories. What can one say about the Caped Crusader except that he is the best superhero out there, simply because he’s neither a hero nor is he super. He’s an rich orphan who tries to do extraordinary things and consequently gets into brawls, both physical and emotional, with truly terrifying villains. It’s odd to think of Batman as an outlaw, but he is – hunted by the police and his enemies alike, the world’s greatest detective stalks the rooftops of Gotham looking bad guys to break. Dark, tormented, brooding and fantastic, Christopher Nolan’s iteration of Batman is my number one outlaw, and my number one comic book hero, and my number one everything. I, like most, cite The Dark Knight as being my favorite film of The Dark Knight Trilogy, but have to admit Christian Bale’s portrayal of the Bat reached its apex in The Dark Knight Rises. Though the film ended up suffered from an identity crisis, Bale’s portrayal of Bruce Wayne was haunting, earnest, and heartfelt. Bravo, Mr. Bale. Bravo.

“Sometimes the truth isn’t good enough. Sometimes people deserve more. Sometimes they deserve to have their faith rewarded.”

Honorable Mentions:

Butch Cassidy and the Sundance Kid–  Paul Newman and Robert Redford
Bonnie and Clyde– Faye Dunaway and Warren Beatty
Richard Kimble– Harrison Ford (The Fugitive)
The Outlaw Josey Wales– Clint Eastwood

Written By Ries

Ries is a writer, blogger, amateur explorer and full time United States Marine. He graduated from DePauw University in 2011 with a Bachelor’s Degree in English and is busy putting that degree to work writing elite movie reviews for sites like CineKatz. In his spare time he enjoys traveling, movie watching, talking to himself in the mirror and working on novels that may or may not ever be finished. Of all the things he misses about being a civilian, he misses his beard the most.

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  • Belinda

    As always great Article Ries!! Sadly i have only seen one of these movies, The Pirates of The Caribbean: The Curse of The Black Pearl (and maybe one of the dark knight movies), and yes i know, i need to step up my movie game. But anywho I love johnny Depp as captain sparrow, and would love to see him as John Dillinger. Oh yes, i loved finding out the monkey’s name was Jack! Thanks for giving me some movies to add to my “i need to watch” list!
    i love the quotes “Even bad men love their mamas.” and “Sometimes the truth isn’t good enough. Sometimes people deserve more. Sometimes they deserve to have their faith rewarded.”

  • Amanda

    Great collection of films, Ries. I haven’t seen several on the list, but this was a great reminder of films I had intended to watch, but then got somewhere in between school work and such. 3:10 to Yuma, No Country for Old Men, and Cowboys vs. Aliens, were all filmed in Ghost Ranch, New Mexico, so when I saw this was “The Six Best Outlaws” I had hoping some of these titles would turn up, as Ghost Ranch seems to be one of the more popular places to film Westerns these days. My question is, where is Anton Chigurh? He’s definitely the most frightening villain, I’ve ever seen in a film, but I guess a villain isn’t the same thing as an outlaw, and maybe I’ve answered my own question. And good call on the Dark Knight Trilogy, for some reason, I hadn’t expected it to show its face in this Pick Six, but it seemed obvious when I saw it. Nice work.

  • Tom

    Hahaha I’m definitely going with the cats in No Country For Old Men. What an unsettling movie. Also, great call including Public Enemy. It was really under the radar, and a great film. Lastly, it’s a crying shame what Disney did to Jack Sparrow. I’m still mad about that.

  • Ries

    Heya, Belinda. I love those quotes too – and you need to see basically every movie on this list. Thanks for stopping by. 🙂

  • Ries

    Hmmm…I would say that Anton Chigurgh is more villain than Outlaw, but if this was a top villains list he would assuredly be on it. Ghost Ranch is certainly a mecca for a lot of desert set films. Batman is definitely an Outlaw – the dark horse, if you will. Heh heh. Thanks for commenting.

  • Ries

    RIP Jack Sparrow. And the Cats are definitely the best on this list. Thanks for commenting, Tom.

  • rich

    i’m a huge eastwood fan, and thus a huge josey wales fan, so he’s at the top of my list of outlaws or almost anything. it was also one of the first dvd’s i ever bought, right behind jaws and monty python and the holy grail.

    however, about them thar outlaws, bed wade was a good one, but i had a problem with the film in its entirety. wade could have easily caused enough of a distraction so that christian bale’s character would have been shot dead, and he would have easily gotten away, but he went along with the capture while continually saying he didn’t want to go along with it. i’m sure there’s something i missed, but it wasn’t made clear enough.

    however, wade was still a good outlaw. or is he an outlaw? what exactly IS an outlaw? wales, batman, butch and sundance, sparrow, even ford and dillinger have redeeming qualities. should an outlaw have a redeeming quality? i believe a vigilante should, but i’m not sure about outlaws.

    either way, it’s still a fun discussion.

  • Ries

    I’m assuredly not a Clint Eastwood fan, though I have been known to enjoy some of his films. (Read: NOT Gran Torino.) I hear you on your thoughts about Outlaws having redeeming qualities, but I have to protest that Outlaws do have redeeming qualities. The way I think of it is this – there are different sub categories. Villains, Outlaws and Vigilantes. All vigilantes are Outlaws, not all Outlaws are vigilantes. Most villains are Outlaws, but not all. Some of the greatest villains operate within the confines of the law. Redeeming qualities are what make any outlaw interesting. And I’m sorry 3:10 to Yuma missed you, but I hope when you get a chance you can revisit it, and maybe it’ll be a little less muddled on a second watch. Thanks for commenting. 🙂