Kevin Spacey: Se7en, Swimming With Sharks, The Usual Suspects, Glengarry Glen Ross, American Beauty, Superman Returns for fuck’s sake. Or Nine Lives for that matter, and 
Baby Driver and Horrible Bosses. The man played Richard Nixon! No one plays mischievous evildoer as well as Spacey, but even his good guys tend to be smug bastards at best. His dialogue comes out razor-sharp, often coated with either sarcasm or condescension, and likely both.
Jeremy Piven: This guy is just insufferable. You can crown him King of Pricks based on his role in Entourage alone, but his screen credits offer further proof: Old School, Sin City, Very Bad Things. The guy even plays sleezy cartoon characters in both Cars and The Pirates! Band of Misfits. His deadpan delivery is infuriating and he has the kind of shit-eating grin that just begs to be slapped. Hard.
Christopher McDonald: I wondered if I was just holding a grudge from Thelma & Louise 
(he played the shitty husband) but no, he followed that up playing Shooter McGavin in Happy Gilmore, and what a fantastically smarmy role that is. He even plays the guy who wants to steal flubber from poor Robin Williams. He has the kind of arched eyebrow that makes me wonder: is he perpetually typecast as a dick, or do characters turn into dicks once played by him? Chicken or egg?
John C McGinley: If you see this guy on screen, you know you’re in trouble. He’s often the
socially awkward dad who gets under everyone’s skin. You just want to snap his unironic suspenders to deflate his pomposity for just a moment. Platoon, Wall Street, Office Space: Hollywood seems to agree that this guy just oozes jerk.
Richard Dreyfuss: He played conceited in Dillinger, self-involved in American Graffiti, self-important in Close Encounters of the Third Kind, egotistical in The Goodbye Girl, pretentious and selfish in Mr. Holland’s Opus, and arrogant in Red. Come to think of it, is he even capable of pretending to be nice? At least he’s a bit sympathetic in Whose Life Is It Anyway; yeah he’s a real jerk to pretty much everyone around him, but the dude’s paralyzed and you cut him some slack. In everything else, you just kind of hate him.
Sam Rockwell: I kind of love Sam Rockwell, but there’s something weaselly about him. 
He seems to get stuck playing the douchebag an awful lot, but to his credit, he has a certain charm that makes the douchebaggery slightly lovable. Except in Iron Man 2: in that one, he’s downright evil, but I think if you’re in a movie with Robert Downey, Jr who plays the lovable scoundrel card pretty hard, you have to go big or go home.
Jason Bateman: you pair that chubby, boyish face with the condescending hot garbage that comes out of his mouth, and you’ve got a goldmine of narcissistic characters on your IMDB page. He’s obnoxious in Bad Words, manipulative in Horrible Bosses, irresponsible in Juno, patronizing in This Is Where I Leave You, bullying in Central Intelligence, a swindler in Zootopia, and downright infuriating in The Ex. This guy plays to his strengths!
Bradley Cooper: He may play a rapscallion, but he’s an irresistible rapscallion. Those dimples let him get away with murder, and sometimes his characters come pretty close. 
He played the lying, cheating husband in He’s Just Not That Into You, the lying, cheating fiance in Wedding Crashers, an amoral arms dealer in War Dogs, a diva in Burnt, a shit-don’t-stick-to-me arse in The Hangover, a corrupt cop in The Place Beyond the Pines, and a reckless raccoon in Guardians of the Galaxy. Does his devilish grin suit him? It does. And Cooper knows it.
Billy Crudup: He didn’t have time for his dying dad in Big Fish. He didn’t have time for his band or for child prodigy journalists or devoted fans in Almost Famous. He puts the nails to a grieving widow in Jackie. He leads people astray in Alien: Covenant. He terrorizes kids in The Stanford Prison Experiment. His characters are not often likeable, even if they aren’t bad. What does it say about Crudup that he’s so good at that?
Jason Schwartzman: This is the guy we love to hate. He’s an angry bear in Listen Up 
Philip, an insecure uppity asshole in Scott Pilgrim Vs The World, a conceited actor in Funny People, and as Louis XVI (in Marie Antoinette), he was the very symbol of tyranny – and that’s without mentioning every smug arsehole he’s played in every Wes Anderson film. He embodies neuroses and self-loathing. Even when he’s playing earnest, he’s coming off overearnest and cloying. He just can’t win, which is why he always plays an asshole.
Who’s on your list?
ASSHOLES WATCHING MOVIES 
One of my favorite Kevin Spacey roles was on the TV show Wiseguy. That character was so evil and flat out crazy, that it made the show. I have followed his career ever since.
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Also loving Kevin Spacey in House of Cards. Jesse Eisenberg quite often plays an asshole. It’s always the same character, too…
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OH yes, he definitely deserves to be on this list…or to have one all his own!
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Willem Dafoe. I like and respect him as an actor mainly because he can play intimidating and charismatic assholes. He’s done some great work but look no further than Spider-Man for great assholishness.
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Yeah, that’s a pretty good one, you’re right, his credits are littered with that type of character!
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I’m making a list but your list is way good!
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This is a great list. I would add Vincent Gallo and Alec Baldwin to the list. Alec is a prick in Glengarry Glen Ross and absolute human slime in The Cooler. He has an air of douchebaggery about him that has served him well in several roles.
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Oh, that’s a terrific one!
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Malice and The Juror too! Baldwin plays smooth scumbags very well!
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I’ve recently watched Whiplash and J.K Simmons would definitely fit this list
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Love this list, and yes, Kevin Spacey. I’d be tempted to add Vince Vaughn. He always plays the asshole who thinks he’s cool and learns a valuable lesson by the end of the film.
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Yeah, he’s another one who makes me wonder – is the character an ass or it just him? His line delivery can seem so flippant and thoughtless.
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Great List and love Kevin Spacey who can also sing and, I bet, dance. Christopher Walken is another loose cannon-I mean his hair says it all. Claude Rains and James Cagney also fit
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Yes, I thought that if I opened up to older actors then the list would never end, but you’re right, there’s a great wealth of them throughout the years.
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Pretty comprehensive list, although I’d leave off Sam Rockwell, he’s awesome.
I’d like to second mydangblog’s shout of Jesse Eisenberg and add Danny McBride and Rob Corddry.
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Ha, I just saw this in my feed and laughed. I am definitely am coming back to read and watch.
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Hugh Grant, in “An Awfully Big Adventure” (hopefully, I’m remembering his character right, it’s been a while since I’ve seen it LOL) and “Cloud Atlas”. James Spader in Pretty in Pink and Mannequin (hee!).
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Oh yeah, James Spader in pretty much anything.
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great post! haha. there’s what about bob? for richard dreyfuss too- plays off lovably dumb-witted Bill Murray so well in that one.
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Definitely all of these, but especially Kevin Spacey!
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🙂 great list!
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These guys are good but no one holds a candle to William Atherton (Ghostbusters/Die Hard) in the a-hole department, IMHO. I’d also add John C McGinley’s role in Point Break to his list.
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Well, you are correct on both points.
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Interesting list. Did you ever see Mr. Selfridge? Jeremy Piven in a period piece. (Well, it’s a series.)
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Haha this is quite the list! I wonder how you came up with the topic? Perhaps because A**holes is in your blog name? I’ll add in Alan Rickman who was in Harry Potter, Die Hard, and Robin Hood. Maybe it’s his voice that really lends itself to the jerk roles? 😉
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Yeah, I have a real soft spot for the guy but you’re right, he’s racked up quite a list himself.
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Hi Jay,
Great list…no debate on the actors you picked. I like Gene Hackman but when he plays a jerk, no one can touch his meanness….Unforgiven, Bonnie and Clyde, The Quick and the Dead, The Firm, Get Shorty, …. the list goes on. I know he is an old guy and your list would go forever; but, I had to mention him 😊
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He’s an excellent addition.
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Nice idea for a list – I remember my wonderful wife correctly observed recently that Ryan Phillipe tends to play an entitled jerk in most of his films!
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You forgot John Travolta OMG!🙆🙆
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LIterally, yes, forgot he existed.
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Great choice, Kevin Spacey is my all time fav. I also love Allan Rickman and Bill Murray being asholess 😀 Murray is awesome because he is a perfect cynic and makes me want to punch him in the face and fall in love with him at the same time ❤️ Oh and Bryan Cranston as Heisenberg is an amazing example
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I hate to think of Rickman as a bad guy but you’re right, he does the icy delivery very well. And Bill Murray is the perfect cynic indeed. He makes it seem charming.
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Great post! Are we doing the actor/actress rule here? If not I would add Meryl Streep for playing a great arsehole in Devil Wears Prada and August: Osage County especially!
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Bradley Cooper? Oh my… Isn’t he supposed to be the next Indiana Jones?
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Cooper and Bateman would both make my list… great call. I’d add Alec Baldwin and Ed Norton. Ed Norton is good at asshole.
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Awesome list! Watching these guys being assholes on screen is pure delight.
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This made me laugh and get angry all at once!
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A fine and solid list of assholes!
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Dabney Coleman is my all-time fave in this area. Why didn’t he have a bigger career?
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Ha! I really enjoyed this list! I would say that Vince Vaughn is a phenom at playing assholes. His part in the movie Made, alone, would get him past the velvet ropes and into the club.
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