Cool as a concept is a lot like the adult film industry – it thrives underground, uptight people hate it and someone invariably mentions James Dean. And most importantly, you just know it when you see it. Cool by its very nature defies definition, and trying to define it is decidedly uncool, and so what we’re left with are cultural examples we can point to and say yup, that’s cool. And so in order to both illustrate and celebrate all things cool, we thought we’d bring you this, the 50 coolest movie characters ever. Cool? Cool.
50 Loki – ‘Thor,’ ‘The Avengers,’ etc.
Sure, the sign might say “Thor,” and in the end he’s going to be the one left standing, but Loki’s the one who wins everybody’s hearts and carries those movies. He gets all the best lines and the best scenes, and he does it with a taut sort of predatory calm that just screams cool.
49 Holly Golightly – ‘Breakfast at Tiffany’s’
Flighty? Sure. Maddening? Maybe. But you can’t deny that Holly Golightly is the epitome of a certain sort of cool, the sort that lets her glide through life, staying just a half a step in front of a world that wants to bring her down, and she always looks good doing it.
48 Tony Montana – ‘Scarface’
Can a coked up maniac be cool? Sure he can, as long as he has the swagger to roll with a goddamn pet tiger and an enormous machine gun. Look, the dude got to live in a big ass mansion and bang Michelle Pfeiffer in her prime. Don’t act like you could do better.
47 John McLane – ‘Die Hard’
It’s hard for a cop to look truly cool. I mean, upholding the law isn’t exactly rebel without a cause kind of stuff, you know? It’s a lot easier when that cop is running around in a wife-beater on broken glass, killing German terrorists all with a sort of world-weary WTF is this nonsense style. Yippee-ki-yay, motherfucker indeed.
46 Trinity – ‘The Matrix’
For as much as The Matrix trilogy consciously strived to be cool, what with the leather daddy outfits and the late-90s techno orgy feel, the only one who really pulled it off without looking vaguely ridiculous was Trinity. She was a badass chick who could stick a gun in an agent’s face, tell him to dodge this, pull the trigger and walk away like a lady pimp.
45 The Wolf – ‘Pulp Fiction’
Look, Tarantino’s going to show up a lot on this list. Part of that is due to the fact that his movies are basically celebrations of cool. But it’s also because the actors and the characters tend to meld so perfectly, which is the case here, as Harvey Keitel brought his quiet menace to this disarmingly friendly character, and in the process left people thinking that in a movie full of badasses, that the Wolf might have been the baddest of them all. Plus, he’s named “The Wolf.” I mean, he pretty much has to be cool, right?
44 Captain Jack Sparrow – ‘Pirates of the Caribbean’
Pirates are cool. Keith Richards is really, really cool. Combine the two, and you have Captain Jack Sparrow. It doesn’t hurt that Johnny Depp, himself an icon of cool, brings the whole package together and lets Captain Jack keep his boozy, woozy brand of cool even though he’s captaining a Disney flick.
43 Tyler Durden – ‘Fight Club’
Tyler Durden is basically the impish ID of every dude who feels marginalized and lied to by the American Dream. Whether or not they deserve to feel that way is another story, but you can’t deny that Tyler Durden’s take no bullshit, laugh in the face of destruction style is cool.
42 Jackie Brown – ‘Jackie Brown’
It’s hard to make a lonely middle aged flight attendant seem cool. But when that flight attendant is played by Pam Grier, it suddenly gets a whole lot easier. She gives the character a soulful, sultry sort of cool, which plays right into Quentin Tarantino’s wheelhouse. The first words from the trailer say it all: “Pam Grier is Jackie Brown.” Indeed.
41 Darth Vader – ‘Star Wars’
Vader is basically a space pimp. He struts around in a big ass cape, chokes out bitches using only his mind, and has to fend off the revenge fantasies of his bastard children. All he’s missing is the cane and cup.
40 Sarah Connor – ‘Terminator 2′
Really, if we’re talking cool, we’re talking about the Sarah Connor from T2. Sure, in the first movie she’s kind of cool, in that she manages to survive long enough to crush robot Arnold, but in the second she’s a full-on badass, doing pullups in her room at the nuthouse, beating the shit out of male nurses, and blasting shotguns at liquid metal freaks. You do not want to mess with that woman.
39 Vic Vega – ‘Reservoir Dogs’
Many people don’t know that the infamous Mr. Blonde from Reservoir Dogs is actually the brother of John Travolta’s character in Pulp Fiction, but hey, now you do. I just want to know how they were raised, because between their shared sociopathy, love of dance, and languid it’s all good style they must have been raised by some truly, uh, special parents.
38 Vincent Vega – ‘Pulp Fiction’
Sure, Vic might have sliced an ear off while casually dancing to “Stuck in the Middle with You,” but Vincent has to be the cooler brother. By just a hair – or an ear, I guess – but still, it’s true. It’s hard to say exactly why, but that’s just the nature of cool. I mean, Vic never got Uma Thurman to grind on his junk, so advantage Vincent.
37 Hard Harry – ‘Pump Up the Volume’
Foul mouthed, brashly funny, Leonard Cohen fanatic… I could go on and on about all the things that make Harry cool, but it’s really all about his wicked tongue combined with an earnest passion that make him a true icon of cool. I mean, really, this was just some dork with a radio in his basement, but by tapping into his inner cool, he managed to get the feds on his ass and get a hot, horny listener to fall in love with him. Talk hard, yo.
36 Scarlett O’Hara – ‘Gone With the Wind’
Scarlett O’Hara was the ultimate single lady just trying to get by in the world, and she did so with a sort of flirtatious and feisty charm that was cool as hell for the 1860s. Sure, she’s got her flaws, but who doesn’t? She’s the spiritual ancestor of every fictional femme fatale that followed, and if a time machine dropped her in Manhattan today, she’d own that whole damn town by the end of the week. True cool is timeless.
35 Django – ‘Django Unchained’
Does it make me weird that writing this kind of makes me want to see a crossover sequel starring Django and Scarlett O’Hara road-tripping through the post-war South, bickering in between towns and boning down in King Schultz’s wagon? Look, if I have to explain why Django of all people is cool, then you’re in the wrong place, friend.
34 Tony Stark – ‘Iron Man,’ ‘The Avengers,’ etc.
Okay, okay, Tony Stark is basically just Robert Downey, Jr. playing a version of himself, but that’s pretty much enough all on its own to make this list. Throw in some badass toys and a touch of inner heroism, and you have one of the coolest comic book movie characters ever.
33 Lisbeth Salander – ‘The Girl With the Dragon Tattoo’
I’m talking the OG Noomi Rapace Swedish version of the character, not the Americanized remake. In that version, Lisbeth Salander is the epitome of 21st century cool, weird enough to make people uncomfortable, but with an odd sort of sex appeal that really makes them uncomfortable. She obliterates the line between genders, renders it meaningless, and shows everyone what the future of cool looks like.
32 Frank Bullitt – ‘Bullitt’
Come on, it’s Steve McQueen, AKA The King of Cool, playing his most iconic character. This is just what American male cool looks like.
31 Harry Callahan – ‘Dirty Harry’
See what I just wrote about Frank Bullitt and then multiply by ten. This is Clint Eastwood being, well, Clint Eastwood. Sure, he’s a cop and kind of a fascist, but… it’s Clint Eastwood! Come on.
30 Marsellus Wallace – ‘Pulp Fiction’
Remember what I said earlier about Tarantino being a master of marrying the character to the actor? Well, this is a perfect example, as Ving Rhames inhabits Marsellus and creates a character you both don’t want to mess with and want to hang out with in the hopes that some of his cool might rub off on you.
29 Dr. King Schultz – ‘Django Unchained’
What’s not cool about a weird little German dentist who rides around in a wagon with a tooth on it as a cover for the fact that he’s actually a cold-blooded bounty-hunter? Yes, it’s weird, but it’s the sort of weird that is actually really, really cool. It also helps when you’re played by Christoph Waltz, whose disarming style belies a complexity that always hints at a deep well of cool.
28 Snake Plissken – ‘Escape from New York’
This is Kurt Russell at his absolute coolest, which is pretty damn cool. Look, anytime you slap a pirate style eye-patch on someone it makes them at least 73% cooler. It’s just basic math.
27 Mia Wallace – ‘Pulp Fiction’
Another Pulp Fiction character? You’re damn right. I’m not going to apologize considering that the movie is basically a monument to all things cool. And Uma Thurman’s Mia Wallace is near the top of the cool list. Everything about her screams cool, and it’s telling that she’s the one on the movie poster even though she’s only a supporting player in Vincent Vega’s storyline. She’s just too cool to ignore.
26 Anton Chigurh – ‘No Country for Old Men’
Anton Chigurh is one of the most unforgettable movie villains ever, and it’s not because he’s wildly over the top, but simply because he’s so cool that it’s terrifying. Deciding a dude’s fate on a coin toss is horrifying because it completely obliterates concepts like good or evil, or even motive, but it’s also something only someone who is supremely cool could pull off. Psychotic and profoundly amoral, yes, but cool doesn’t care about your values, Middle America.
25 Michael Corleone – ‘The Godfather’
Michael is cool in the same way Anton Chigurh is cool. There is something horrific about him, but he can pull it off because of the sheer force of his personality. He’s the man, the boss, and in order to be the alpha, you have to be cool.
24 Bill – ‘Kill Bill’
Bill is just a dude who likes to hang with the ladies and maybe teach them to kill people. You know, just ordinary cool dude stuff. But what really puts Bill over the top is his death scene. He goes out like a goddamn boss, and shows that even in death – or maybe especially in death – cool isn’t something you can ever take away.
23 The Dude – ‘The Big Lebowski’
The Dude is so cool that his name is actually “The Dude.” Case closed.
22 Coffy – ‘Coffy’
This is Pam Grier kicking all sorts of ass and looking fly as hell while she does it. Blacksploitation, feminist icon… it doesn’t matter how you classify Coffy, because in the end, she’s the type of cool that defies categorization.
21 Luke – ‘Cool Hand Luke’
Luke is all about nonconformity, even in the face of brutal prison conditions. He’s just gonna do what he’s gonna do, and that’s that, which is pretty much the heart of cool. I mean, come on, the movie poster shows him just reclining in the sun, shirt half undone, a cigarette dangling out of his mouth like he’s loungin’ on the beach somewhere instead of suffering in prison. Now that’s a cool dude.
20 The Sundance Kid – ‘Butch Cassidy and the Sundance Kid’
Really, it doesn’t much matter whether you prefer Butch or Sundance because they’re both cool in their own ways. Sundance is the calmer, more badass version of the two, and you can see why the ladies would flock to his junk.
19 Butch Cassidy – ‘Butch Cassidy and the Sundance Kid’
On the other hand, Butch gets by on his wits and his, well, on his cool. That means something, you know? Sundance has his gun, Butch has his mouth. Both are cool, but one is all personality, and that gives Butch a slight edge. Plus, he’s played by Paul Newman. That, uh, that helps.
18 John Shaft – ‘Shaft’
He’s Shaft. End of discussion.
17 Bodhi – ‘Point Break’
I’m going to be honest with you – Point Break is my favorite movie ever, and Patrick Swayze is my spirit animal so you’re lucky the whole list isn’t just made up of his characters. But in the spirit of professionalism (shut up) I decided to go with just Bodhi, who lived his life like a candle in the radical wind, and… I’ll be right back, I need to think about some things.
16 Tuco – ‘The Good, the Bad and the Ugly’
Tuco is so cool that even though he is “the ugly,” and even though he’s paired up with Clint Eastwood of all people, he’s the one you end up rooting for. That’s an almost impossible trick to pull off, and yet Tuco manages to capture hearts with his combination of bravado and dirt-bag cool. You can’t deny the cool status of any dude who shoots a guy who won’t shut up and then says, “If you’re going to shoot, shoot. Don’t talk.”
15 Rhett Butler – ‘Gone With the Wind’
“Frankly, my dear, I don’t give a damn,” followed by a quick pimp-strut exit is about as ice cold a movie scene as there’s ever been. I don’t care how cool Scarlett was, Rhett took her cool and cracked it right in half with that beauty, and with that he took her cool, because just like in Highlander, there can be only one. Incidentally, that reference proved that I am decidedly uncool.
14 Ferris Bueller – ‘Ferris Bueller’s Day Off’
Ferris Bueller was so effortlessly cool that it’s almost a legitimate question to wonder if he’s actually a sociopath. That’s because nothing seems to faze him, least of all mortal, human feelings. Either that or he’s a robot, a robot programmed to be the coolest teenager who ever lived.
13 Ellen Ripley – ‘Alien’
Ellen Ripley is so cool that even the unstoppable monster aliens who went head up with the Predator in all those stupid spinoffs couldn’t step to her without getting clowned. While all the dudes on her various voyages were busy getting waxed and chest exploded, Ripley said to hell with all that and just got down to the business of killing aliens. She doesn’t have time for any of that alien’s bullshit.
12 Jules Winfield – ‘Pulp Fiction’
Finally, we come to the coolest character in Pulp Fiction, which makes sense because, well, it’s Samuel L. Jackson, AKA the dude with the wallet that says “badass motherfucker” on it. It doesn’t matter whether he’s quoting scripture like some homicidal preacher or arguing about Big Macs and foot rubs, he’s the coolest dude in any room.
11 Keyser Soze – ‘The Usual Suspects’
It’s all about that final scene, man. Never has a character been defined as so cool so quickly and so indelibly as in that scene. Verbal’s transformation into the uber-cool Keyser Soze was so amazing it basically won Kevin Spacey an Oscar.
10 Rick Blaine – ‘Casablanca’
Tangling with Nazis all while running the coolest bar in the Mediterranean and making your lady fall back in love with you even though her current dude is basically James Bond pretty much makes you one of the coolest guys who ever lived. And if that wasn’t enough, Rick pulls the coolest move ever by telling the woman he loves to get on that plane and go with her spy lover because it’s for the best. And then he walks away like a boss. Cool.
9 Axel Foley – ‘Beverly Hills Cop’
This is Eddie Murphy at his coolest, which is one of the coolest people in the history of the planet, so… yeah. Nothing got to Axel, who stands as a symbol for tough, unflappable, funny Detroit cool to this day.
8 The Man With No Name – The ‘Dollars’ Trilogy
This is the defining Clint Eastwood character, which means that whenever anyone talks about how cool Clint is, they’re probably actually talking about this character. He’s a man of few words, who with a squint and a gun just rides from town to town, owning douchebags. He is the ultimate American cowboy, which is the ultimate symbol of American cool.
7 The Joker – ‘The Dark Knight’
Heath Ledger’s version of the Joker was so cool that by the time it was over, you were almost sad that he didn’t win. How cool is he? Well, he can walk into a meeting of Gotham’s most vicious crime lords wearing face paint, and terrify them all into subservience just by performing a homicidal magic trick involving a pencil.
6 The Bride – ‘Kill Bill’
And here she is, the coolest Quentin Tarantino character of them all. She’s the only person in Bill’s world who can out-cool him. He knows it, and so does everyone else who ends up on her bad side, and in the end it turns out that’s almost everybody. Never try to out-fight – or out-cool – the Bride, because you will lose.
5 Indiana Jones – ‘Raiders of the Lost Ark’
The defining Indiana Jones cool moment has to be the scene where he just casually shoots a dude who’s swinging swords like a maniac. You have to be cool to get away with that sort of thing, and whether it’s that, or whether it’s Indy romancing everyone from ditzy actresses to Nazi ice queens, there can be no doubting the coolness of Indiana Jones.
4 Peter Venkman – ‘Ghostbusters’
This is Bill Murray showing up, acting like Bill Murray for two hours, and then saving the world before making out with Ellen Ripley. It doesn’t get much cooler than that.
3 Johnny Stabler – ‘The Wild One’
“What are you rebelling against?” “What do you got?” And with that exchange, Marlon Brando defined cool for an entire generation. It sounds almost silly to say, but it was a landmark moment in pop-culture, one where “cool” finally became, well, cool.
2 James Bond – Countless ‘Bond’ films
He’s James Bond. What more do you need? People use his name as a synonym for cool.
1 Han Solo – ‘Star Wars’
This is probably my inner dork speaking, but really, who’s cooler than Han Solo? He’s so cool that in the movie 500 Days of Summer, after the main character bones Zooey Deschanel, he’s feeling so unbelievably cool that he looks in a window to see his reflection only to see Han Solo smiling back at him. That’s how cool he is. A dude had to bone Zooey Deschanel to even think for a fraction of a moment that he was as cool as Han Solo. Han Solo isn’t just cool, he’s I Just Boned Zooey Deschanel cool.
(Previously published on December 18, 2013.)
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