Bad bosses: The 25 most evil & megalomaniacal CEOs in film

The Senior Vice President of Omni Consumer Products (Ronny Cox) might’ve answered to “The Old Man” (Dan O’Herlihy), but he built up enough institutional goodwill to not only oversee the development of a crime-fighting robot outfitted with machine gun arms, missiles, and other military-grade weaponry but to actually keep his job after said robot, the ED-209, poured piping hot lead into a junior executive during a boardroom demonstration. Jones killed Bob Morton because he made a mistake called Robocop, but Morton got the last laugh when the cyborg’s classified fourth directive was annulled. So much devilry and yet the nastiest thing about the guy was his men’s room etiquette.

“You have meddled with the primal forces of nature, Mr. Beale, and I won’t have it!” Thus begins one of the most riveting monologues to ever boom from movie theater speakers. It’s a warning and a directive from CCA chairman Arthur Jensen (Ned Beatty) to Howard Beale, “the mad prophet of the airwaves” whose nightly missives have shaken American TV viewers from their couch potato stupor, and it is necessitated when the newsman-turned-preacher attempts to block the sale of his network to a Saudi Arabian conglomerate. Beatty roars like an angry god; his delivery is borderline cartoonish, but, as we’ve learned over the last forty years, men like Jensen have a bite that’s every bit the equal of their bark.

Paul Reiser was still a year away from being a lovable sitcom patriarch on My Two Dads when he delivered the most noxious depiction of ‘80s Yuppie Scum (this side of Steff McKee at least) in Aliens. Perhaps that’s the most frightening notion in James Cameron’s sci-fi/horror/action classic: these greedy corporate suck-ups still sully the ecosystem 200 years later. Burke comes on as a compassionate corporate suck-up, but we soon learn his mission objective is quite different from Ripley’s and the military’s, and he’s willing to kill to achieve it.

There isn’t a more horrifying moment in film history than the image of Los Angeles water mogul Noah Cross (John Huston) extracting Katherine Cross (Belinda Palmer), the granddaughter he sired, from the car in which the young girl’s mother/Cross’s daughter, Evelyn Mulwray (Faye Dunaway), lies dead from a gunshot to the head. Cross’s feigned grief paired with Katherine’s unbearable anguish stays with you forever. Huston had an effortless malevolent authority about him, but he never put it more indelible use.

Dan O’Herlihy was a genuine movie star in the 1950s (he earned a Best Actor Oscar nomination for his lead role in “Robinson Crusoe”), but most Gen X-ers know and love him for his supporting roles in classic ‘80s B Movies like “The Last Starfighter”, “RoboCop” and, of course, “Halloween III: Season of the Witch”. As mask-making mogul Conal Cochran in the franchise’s Michael Myers-less third installment, O’Herlihy does a nifty slow-burn from a sweet old man to genocidal pagan witch. It’s more satisfying than his heel turn as “The Old Man” in “RoboCop 2” if only because “Halloween III” isn’t a lousy movie.

When executive Waring Hudsucker (Charles Durning) hurled himself from a boardroom window to the unforgiving concrete many stories below, he kicked open the door for Sidney J. Mussburger (Paul Newman), a conniving, greedy son-of-a-bıtch who uses a moron (Tim Robbins) to gain control of the soon-to-go-public company. When the moron hits upon the moneymaking fad of the decade (i.e. the hula-hoop), Mussburger plots to destroy the moron’s life. Newman has a grand ol’ time as a cigar-chomping bāstard of industry.

Small-town tyrant Henry F. Potter (Lionel Barrymore) has designs on the Bailey Building & Loan, but George Bailey (James Stewart) won’t capitulate to his wealthy shareholder’s demands no matter how much the business struggles. Like many successful executives, Potter employs the full range of coercion (from bullying to flattery to bullying again) to get his greedy paws on the Building & Loan. His devastating line to George (“You’re worth more dead than alive!”) drives the good-hearted man into a suicidal spiral.

Commodities titans Randolph and Mortimer Duke (Ralph Bellamy and Don Ameche) wager “the usual amount” to settle a long-running dispute about nature versus nurture. In the process, they ruin the life of well-bred broker Louis Winthorpe III (Dan Aykroyd) while elevating street-smart conman Billy Ray Valentine into the latter’s prestigious position. For the Dukes, this is a divertissement to their highly criminal scheme to corner the market on FCOJ (Frozen Concentrated Orange Juice) futures. The Dukes might come off as kindly old men, but they’re corrupt as hell and viciously racist.

Ebenezer Scrooge should be on here, but it’s impossible to pick the best big-screen Scrooge (Albert Finney and Michael Caine are in a virtual tie). As for an off-brand Scrooge, there’s only one Frank Cross and only one Bill Murray. How evil is network executive Cross in “Scrooged”? He airs a hyper-violent North Pole siege film called “The Day the Reindeer Died”, sends his only brother a company towel for Christmas, and suggests stapling antlers to mice for his station’s live production of “A Christmas Carol”. Before Cross has his obligatory change of heart, he gets into a knock-down, drag-out fistfight with the Ghost of Christmas Present (Carole Kane).

John Glover’s Trumpish Manhattan magnate was conceived at a time when the future and now former POTUS was viewed – on a national level, at least – as a gregarious, harmlessly doltish talk show guest. This is the genius of Joe Dante’s creation; Clamp’s very real accomplishments (which predated the Disneyfication of Times Square by six years) are nothing to laugh about. He’s appropriated the culture of New York City and driven the actual culture off the island. He is an invasive corporate entity whose building is flooded with creatures that hail from one of the cultures he’s attempting to assimilate. In other words, the Gremlins are not the bad guys here.

In 1989, there was nothing wrong with slūt-shaming a gold-digging former Las Vegas showgirl hellbent on moving her deceased husband’s godawful baseball team from Cleveland to Miami. Nowadays, her treatment might raise some eyebrows. Seriously, had Rachel Phelps (Margaret Whitton) blown into Cuyahoga County and poured loads of money into the then moribund franchise, she would’ve been hailed as a nose-thumbing, anti-establishment hero. Instead, she’s a greedy floozy a la Melania Trump seeking to steal the soul of a hard-luck city. She’s a bad person who gets what she deserves. And the late, great Whitton makes her deliciously hissable.

“My empire is crumbling!” Dana Carvey and Mike Myers can fight all day about who does the better Lorne Michaels; you’ll never see a better Lorne than Mark McKinney’s portrayal of pharmaceutical kingpin Don Roritor in the criminally underseen Kids in the Hall: Brain Candy. Roritor is the kind of executive who’s hard to read because he doesn’t seem to be fully human. He doesn’t care if the company’s new antidepressant is safe; he just wants it on the market.

We skipped Ebenezer Scrooge because there’s not a definitive big-screen Scrooge as of yet. Not so with Superman’s archrival. Gene Hackman plays the criminal/corporate genius with a mischievous wink and the gladdest of hands, supremely confident he’s twelve moves ahead of everyone he encounters. Luthor’s always cocky in the comics, but he’s so much more interesting when he’s trying to be liked. Luthor hates those below him, but he pours on the charm when he wants to get over on his opponent.

John Milton (Al Pacino) is the devil. He’s evil incarnate. And yet he’s not without certain wisdom. Milton sucks in Kevin Lomax (Keanu Reeves), a seemingly decent attorney who betrays his conscience and goes for a big New York City legal gig. Lomax has the makings of a powerful corporate attorney, which is, of course, the kind of talent Satan can’t ignore. Taylor Hackford’s film is a hilariously overheated morality play, but, boy, is it entertaining. And Pacino hurls every last ounce of his emotive gifts into this portrayal.

“The game was created to demonstrate the futility of individual effort, and the game must do its work. The Energy Corporation has done all it can, and if a champion defeats the meaning for which the game was designed, then he must lose.” Mr. Bartholomew (John Houseman) is the ruthless CEO of the corporation that mollifies the populace with the violent spectacle of Rollerball. When the game’s top athlete, Jonathan E. (James Caan), attains global popularity, Bartholomew asks him to resign. When Jonathan refuses, Bartholomew changes the rules of the game to ensure the star’s death. Norman Jewison should’ve dedicated the film to Curt Flood.

How do you make insurance company executive look more loathsome than they already are? Have them take the stand in a courtroom wearing a plush blue sport coat that looks like a bathrobe. It’s beyond tacky. Roy Scheider is a velvet painting of corporate evil. What’s more, he considers his mere appearance in the courtroom, and the grieving plaintiffs, beneath him. He can’t lose. Though his company does, indeed, lose big via punitive damages, the safety net of bankruptcy ensures he’ll never have to pay his victims a cent.

Daniel Day-Lewis won his second Best Actor Oscar for his portrayal of unfettered greed and ambition. Plainview is a man motivated strictly by the accumulation of wealth and power; he is the American id run amok in a land of untapped fortune. It’s right there in the name: “Plainview”. He’s as single-minded in his consumption as the great white shark from “Jaws”: all he does is drill and profit. When his son proves disinterested in the family business, Plainview disowns him. On the plus side, he beats charlatan preacher Eli Sunday (Paul Dano) to death during the film’s denouement.

It’s hard to believe there was a time when people thought David Fincher and Aaron Sorkin went too hard on the Facebook co-creator. Now that his website has allowed millions of halfwits to share their coworkers’ ill-informed screeds about Barack Obama’s parentage, the “Deep State” and the efficacy of vaccines, Jesse Eisenberg’s portrayal of Zuckerberg as a bitter, credit-hogging nerd plays like a love tap.

Thomas Sandefur is the opposite of Arthur Jensen. As written by Eric Roth and portrayed by Michael Gambon, the real-life Brown & Williamson CEO doesn’t have to rail at ex-employee Jeffrey Wigand (Russell Crowe); he just has to gently remind the soon-to-be whistleblower that he can very easily and swiftly ruin his life. Sandefur can also lie about the lethality of his company’s product under oath without betraying a hint of compunction because said feeling isn’t accessible to monsters.

Oliver Stone’s melding of ‘80s corporate raiders Michael Milken and Ivan Boesky earned Michael Douglas a Best Actor Oscar, and, perhaps inadvertently, turned greed into a virtue for a whole generation of investment bankers. Gordon Gekko is a vulgarian who lives, sleeps, and screws (metaphorically… for the most part…) money. He’s got slick-backed hair like Pat Riley and speaks in epigrams. Aside from a total lack of scruples, he’s the ultimate business role model – which, for far too many corporate aspirants, makes him the ultimate business role model.

Much like her real-life inspiration, Anna Wintour, Miranda Priestly does not own the fashion publication she edits, but she certainly acts as she does. Wintour’s reign of terror at Vogue inspired Lauren Weisberger’s bestselling roman à clef , which begat David Frankel’s 2006 blockbuster. Priestly could’ve been your run-of-the-mill ice queen, but Meryl Streep finds a tangible degree of cruelty in the role; she is as her industry designed her, and she soothes whatever’s left of her conscience by knowing that everyone under her would kill (perhaps literally) to seize her throne. She loves her job too much, and thinks too little of her employees, to give them the pleasure.

An upper-management tyrant who masks his tyranny in monotone, Bill Lumbergh (Gary Cole) is far more familiar to most office drones than the fury of a Frank Cross. Writer-director Mike Judge obviously put in his time under a Lumbergh, and he captures the deceptive listlessness that lures young employees into thinking they can phone it in until they find a new gig. As Stephen Root’s zonked-out Milton demonstrates, the end isn’t getting fired; the end is twenty years down the road when you’re just showing up to do the Lumbergh’s, or his successor’s, bidding.

The image-conscious Tom Cruise doesn’t like to take risks, nor does he enjoy biting the hand that’s fed him through thick and couch-jumping thin – which might explain why his portrayal of a megalomaniac studio exec is as shockingly funny as it is frightening. There are traces of Scott Rudin, Joel Silver, and a smattering of Don Simpson’s hedonism, but it’s mostly over-the-top egotism, and it comes awfully easy to Mr. Cruise. There isn’t a molecule inside Grossman’s body that isn’t dedicated to dominating people, his industry, and, just maybe, the world.

Pro sports owners are known for their ego-driven micromanaging and willingness to look the other way when one of their players gets busted for domestic violence or accused of murder. They are, by and large, awful people. Screenwriter Shane Black understood this way back in the early 1990s and made hay with the corrupt, homicidal owner of the Los Angeles Stallions, Shelly Marcone (Noble Willingham). Alarmed by a precipitous dip in TV ratings, Willingham aims to legalize sports gambling in the United States, and he’ll kill anyone, even little Danielle Harris if they get in his way.

Andrew Garfield’s quixotic quest to solve a series of dog murders in his Silverlake neighborhood leads him down a bewildering rabbit hole that eventually leads to the mansion of an ancient, Phil Spector-esque recording industry giant (Jeremy Bobb) who brags that he’s written every meaningful piece of music in human history. Before Garfield can further investigate the Songwriter’s extraordinary claims, the old man tries to shoot him. Garfield finishes the vicious codger off with what was apparently Kurt Cobain’s guitar.