• 16 Craziest Businessmen And Women In Movies
    Leonardo DiCaprio in Wolf of Wall Street
    Leonardo DiCaprio in Wolf of Wall Street

    The Founder drops in theaters on August 5 and threatens to pull back the curtain on the life of McDonald's founder Ray Kroc. Michael Keaton will step into the lead role, and director John Lee Hancock's film is already generating Oscar buzz. That said, what better time to look at some of the other big business influencers as portrayed by Hollywood?

    When selecting the 16 Craziest Businessmen and Women in Movies, we primarily looked for examples that were either direct portrayals of real moguls or examples directly inspired by real people. We also threw in a few fictional favorites for good measure. In each case, these guys (and gals) can teach us a thing or two about business savvy through their sheer mad genius.

    Of course, you probably won't want to take every lesson to heart. After all, the word "craziest" isn't always a good thing.

    Swipe to continue
    Use your keyboard arrows to navigate
  • 16 / 16
    Patrick Bateman (American Psycho)
    Christian Bale in American Psycho

    If Patrick Bateman comes across a little Nic Cage-like, there's a reason for that. Christian Bale said he modeled his American Psycho performance on the actor's role in Vampire's Kiss — you know, the one where Cage eats a real cockroach? While Bale doesn't do anything along those lines, Bateman brings plenty of nastiness to the proceedings.

    As a cutthroat New York investment banker by day, his transition to gore-drenched serial killer by night isn't much of a stretch. Using an axe, a chainsaw and a callous indifference for humanity, he cuts a swath of violence through the streets of NYC with hope for a release it will bring, one that never really comes. In the end, he is a prisoner of his own boredom. From a business perspective, what we learn from Bateman is that money can't buy you happiness, nor can the ability to do whatever you want whenever you want. You need a deeper purpose.

    Swipe to continue
    Use your keyboard arrows to navigate
  • 15 / 16
    Michael Burry/Jared Vennett (The Big Short)
    Christian Bale and Ryan Gosling in The Big Short

    Michael Burry (Bale again) and Jared Vennett (Ryan Gosling portraying a character inspired by Greg Lippmann) didn't create the credit default swap (CDS), but they certainly profited from it at the expense of thousands of high-risk homeowners. The Big Short is their story, and it's a depressing example of how our economic system sets people up to fail while rewarding those who prey on it. Burry's foresight into the collapsing U.S. housing market — before anyone realized it was collapsing — allowed him to earn a nearly 500 percent return on his hedge fund.

    When Vennett confirms Burry's findings, he also discovers that unsellable loans are being converted into collateralized debt obligations (CDOs) and awarded false AAA ratings by conflicted credit reporting agencies. Undeterred by what that could mean to the economy, Vennett cashes in. The lesson these two guys can teach us isn't exactly altruistic, but it is worth learning if you live in the U.S. — namely, if you find a weakness in the system, exploit it.

    Swipe to continue
    Use your keyboard arrows to navigate
  • 14 / 16
    F. Ross Johnson (Barbarians at the Gate)
    James Garner in Barbarians at the Gate

    Barbarians at the Gate was a made-for-HBO film that hit the airwaves in 1993. It starred James Garner in what was arguably his best role as real-life self-made man F. Ross Johnson, the head of RJR Nabisco, who decides to take the company private after the Premier cigarette debacle. ("A turd with a tip on it!?") The lab scene wherein Johnson's men break the news to him is still hilarious close to 25 years after-the-fact.

    The film is based on a book of the same name by Bryan Burrough and John Helyar. Television producer and director Glenn Jordan does a great job of bringing complex material to life in a digestibly hilarious dose. As for Johnson, his failed attempt at a leveraged buyout of his own company would have ended up placing thousands of Nabisco workers on the unemployment lines. The fact he came up short teaches us how greed can so easily backfire, no matter your level of business savvy.

    Swipe to continue
    Use your keyboard arrows to navigate
  • 13 / 16
    Mark Zuckerberg, The Social Network
    Jesse Eisenberg in The Social Network

    Mark Zuckerberg (Jesse Eisenberg) is a young Harvard geek rejected by his girlfriend and intent on using his computer know-how for payback. This leads him to create the misogynistic Facemash website that allows users to grant hot-or-not status to photos of campus females he illegally hacked, earning him a six month academic probation in the process. The popularity of the site and his brief notoriety attract the attention of a couple of social networking pioneers in the Winklevoss twins, university rowers who want Zuckerberg to help them make their Harvard Connection website a reality.

    Zuckerberg turns to friend Eduardo Saverin for financial help in getting a similar creation—Thefacebook—off the ground. As the site gets more popular, it puts Zuckerberg at odds with all three men. Double-crosses, sore feelings, and court settlements ensue. By film's end, Zuckerberg is the world's youngest billionaire, but it has cost him more than a few relationships in the process.

    Swipe to continue
    Use your keyboard arrows to navigate
  • 12 / 16
    Erin Brockovich (Erin Brockovich)
    Julia Roberts in Erin Brockovich

    Erin Brockovich, an unemployed single mom with three kids, stumbled upon a vast cover-up perpetrated by the Pacific Gas and Electric Company (PG&E) in the early 1990s. PG&E was moving to purchase the home of a Hinkley, California, woman who was riddled with tumors. The woman gushed about how good PG&E was to her and her husband, who suffered with Hodgkin's lymphoma. The more Brockovich dug into the case, the more cancer cases that she found directly tied to PG&E.

    Even though she possessed no formal law degree, Brockovich proved to be instrumental in bringing a class action lawsuit against the company and revealing a willful cover-up of carcinogen contamination that went back a quarter of a century. In the end, PG&E had to pay out $333 million to be distributed among 634 plaintiffs (more than $525,000 per person). Brockovich was paid $2 million for her efforts — and that was before Julia Roberts played her in the movie.

    Swipe to continue
    Use your keyboard arrows to navigate
  • 11 / 16
    Billy Beane (Moneyball)
    Movie Details Make Sense Moneyball

    Moneyball follows Oakland Athletics general manager Billy Beane (Brad Pitt) and his assistant GM Peter Brand (Jonah Hill) as they work to field a competitive team in 2002's rebuilding season despite their limited budget. The solution: sabermetrics. Derived from the acronym SABR (Society for American Baseball Research), sabermetrics involves the empirical analysis of in-game baseball statistics. The model allows them to invest in undervalued, high-performing players -- to get the most bang for their buck.

    To everyone's surprise, the model takes the young A's team to a second consecutive postseason appearance after a record-setting regular season win streak. While it didn't result in a championship for Beane, it did serve as an example that would eventually take the 2004 Boston Red Sox to a World Series Championship—the one that ended the supposed "Curse of the Bambino." Today, Beane remains with the Oakland A's organization, now serving as the company's Executive Vice President of Baseball Operations. He and Brand (real name Paul DePodesta) effectively popularized data-driven decision-making on the sports field. DePodesta is currently the strategy officer for the Cleveland Browns.

    Swipe to continue
    Use your keyboard arrows to navigate
  • 10 / 16
    Miranda Priestly (The Devil Wears Prada)
    Meryl Streep in The Devil Wears Prada

    Meryl Streep's performance as Miranda Priestly is at times funny, poignant and infuriating. She is a woman who treats others like soulless playthings that she can bend to her whims without any fear of repercussions. Calling her a "boss from Hell" is putting it lightly, as she tasks her beleaguered junior assistant Andrea (Anne Hathaway) with impossible challenges like illegally obtaining copies of the new Harry Potter book for her children before its release date in order to keep her job. She routinely pulls the rug out from under people who are loyal to her and steps on her competition.

    That said, she clearly cares for her underlings in her own way, as evidenced by the recommendation that she gives Andrea in spite of the younger woman's eventual revolt. You get a sense from Priestly that ruthlessness and cruelty are necessary evils, and that she utilizes both in order to prepare her charges for their eventual independence. The character is said to be a fictionalized version of Vogue editor Anna Wintour, a tough-as-nails second generation publishing magnate and daughter of the British newspaperman Charles Wintour.

    Swipe to continue
    Use your keyboard arrows to navigate
  • 9 / 16
    Preston Tucker (Tucker: The Man and His Dream)
    Jeff Bridges in Tucker The Man and His Dream

    Preston Tucker (portrayed in the film by Jeff Bridges) was a man ahead of his time. A pioneer in the art of nimble entrepreneurship, he dared to take on the big three auto manufacturers of the period. His "dream" would eventually unravel when the companies along with the U.S. Securities and Exchange Commission (SEC) — some say with the goading of Michigan Senator Homer S. Ferguson — hatched a phony investigation that would lead to the company's downfall, in spite of the fact that Tucker was eventually cleared of their "charges."

    Tucker's cars are considered superior in design and performance to much of what was being manufactured at the time. The only line that was ever produced was the Tucker 48. Exactly 51 models rolled off the assembly line before Tucker was forced to shut down. Francis Ford Coppola, director of Tucker: The Man and His Dream, owns one of the remaining cars. Boasting a $4,000 sale price when they first hit the market, some of the remaining antiques have gone for seven figures in recent years, with one going for around $1.2 million. The lesson: he with the best product doesn't necessarily win, but quality will endure.

    Swipe to continue
    Use your keyboard arrows to navigate
  • 8 / 16
    Howard Hughes (The Aviator)
    Leonardo DiCaprio as Howard Hughes in The Aviator

    Leonardo DiCaprio had turned in some pretty great performances before stepping into the role of deeply troubled genius Howard Hughes, but nothing he's done before or since comes close to this tour de force. If you've ever been around someone truly afflicted with OCD, then you can appreciate the realism he brings to this role. The "show me the blueprints" scene in particular was like a page out of a certain Screen Rant writer's childhood.

    In spite of the somewhat debilitating condition, DiCaprio makes the switch to Hughes' genius moments pretty smoothly, helped along by a great cast that includes John C. Reilly and Matt Ross as his "handlers," Noah Dietrich and Glenn Odekirk, respectively. Cate Blanchett's turn as real-life Hughes' love interest and silver screen legend Katharine Hepburn is also a standout. But most impressive is Leo's take on Hughes himself. The man was able to overcome his eccentricities to become a successful film producer and an aviation magnate, whose accomplishments continue to touch our lives with a Steve Jobs-like efficacy some 40 years after his death.

    Swipe to continue
    Use your keyboard arrows to navigate
  • 7 / 16
    Norma Rae (Norma Rae)
    Sally Field in Norma Ray

    Norma Rae is a fictionalized account of the real-life Crystal Lee Sutton, a North Carolina woman who successfully stood up against the J.P. Stevens Textiles mill at the expense of her job. In the film, Sutton/Rae is portrayed by Sally Fields, who won a Best Actress Oscar for her work. Rae is troubled by the diminishing health of those in her family who were unfortunate enough to work at the mill their whole lives. Despite being a minimum wage worker with little education, she sees something isn't right with the working conditions and pushes her co-workers to unionize.

    With the help of union organizer Reuben Warshowsky (Ron Leibman) and the eventual support of her husband Sonny (Beau Bridges), she forces an election at the mill and successfully gets the plant to unionize. The business lesson here: you have the power to create change no matter where you find yourself at in your career. It just takes courage and the ability to align yourself with the right people.

    Swipe to continue
    Use your keyboard arrows to navigate
  • 6 / 16
    Charles Foster Kane (Citizen Kane)
    Charles Foster and Orson Welles in Citizen Kane

    The enigmatic Charles Foster Kane (Orson Welles) has lived a controversial life, and when we first meet him in Citizen Kane, he is at the end of it. With his dying breath, he utters the word "Rosebud" while holding a snowglobe, which subsequently slips from his hand and shatters on the ground. The rest of the film we follow reporter Jerry Thompson (William Alland) as he seeks to solve the mystery behind Kane's final word.

    This will entail interviewing all surviving colleagues, friends, and adversaries from Kane's childhood to the present. Thompson learns that before Kane's successful career in yellow journalism, he was a poverty-ridden youngster in Colorado. After a gold mine is discovered on his mother's property, those fortunes changed, but they created a sour and vindictive man. It isn't until the film's conclusion that the audience learns what none of the other characters in the film ever do — "Rosebud" was the name on the sled Kane was riding the day his mother sent him away to live with and be "properly educated" by banker Walter Parks Thatcher (George Coulouris). Kane spent the rest of his career tearing down Thatcher and anyone else in his path for taking from him the life he always wanted but was never allowed to have.

    The obvious lesson: money doesn't buy happiness. (Of course, neither does poverty.)

    Swipe to continue
    Use your keyboard arrows to navigate
  • 5 / 16
    Gino Monetti (House of Strangers)
    Edward G Robinson and Gino Monetti in House of Strangers

    Edward G. Robinson played a lot of scummy bad guys throughout his 60 years in the business, but one of our personal favorites — and one ideal for this collection of the craziest businessmen in movies — is that of Gino Monetti, the father from Hell who turns all four of his sons against him, in 1949's House of Strangers.

    Monetti is an Italian-American banker of dubious ethics who finds himself indicted on a list of completely justified criminal charges. Three of his four boys turn on him immediately, while a fourth, Max (Richard Conte) plays the role of dutiful child rushing to his dad's aid in a desperate attempt to clear him of the charges.

    Not only does Max fail, he gets thrown in the pen himself for seven years for trying to bribe a juror. When he gets out of the joint, he has a great deal more clarity and realizes what a louse his old man was. He spends the rest of the movie fighting the suspicions of his brothers while literally trying to stop two of them from killing each other. Needless to say, the father Monetti teaches us the negative effects of blurring the lines between family and business.

    Swipe to continue
    Use your keyboard arrows to navigate
  • 4 / 16
    Jordan Belfort (The Wolf of Wall Street)

    Leonardo DiCaprio as Jordan Belfort, and Jonah Hill hug in The Wolf of Wall Street

    Jordan Belfort (DiCaprio again) is a stockbroker intent on taking the easy way out, and for a while it's a strategy that pays off, earning him as much as $22 million in a three-hour span. The problem with this: his "chop stock," or "pump and dump," scheme on penny stocks defrauds investors and draws the ire of the Federal Bureau of Investigation (FBI). Thoroughly resourceful, Belfort enlists the aid of family and friends to keep the earnings coming, off-shoring a large amount of his fortune to a Swiss bank account under the name of his Aunt Emma.

    Belfort would soon find out firsthand that crime doesn't pay after his arrest and conviction. TheRichest estimates his current net worth at -$100 million. Still, he served only three years in a minimum security prison for his part in the dirty dealings, and today commands a pretty impressive fee as a motivational speaker. (Also, any time DiCaprio plays you in a movie directed by Martin Scorsese, it can't be all tragedy.)

    Swipe to continue
    Use your keyboard arrows to navigate
  • 3 / 16
    Blake (Glengarry Glen Ross)
    Alec Baldwin in Glengarry Glen Ross

    Glengarry Glen Ross is a mystery drama centering on a group of real estate salesmen forced into a vicious boom-or-bust sales promotion that will see great fortune for the winners and utter ruin for the losers. The "prize" for the top two salesmen are the highly coveted Glengarry leads. The runner-ups get fired. While most of the film centers on the quartet of men competing against one another, a standout is ruthless sales motivator Blake (Alec Baldwin), who sets the terms of the promotion in the first part of the film.

    Blake is a cruel, foul-mouthed character not unlike that infamous voice-mail the man who plays him left for his daughter a few years back. Of course, here the motivations are different. To Blake, a good verbal berating isn't about getting a few things off your chest; rather, it's the perfect way to whip an underperforming sales agency into shape. David Mamet's script doesn't exactly endorse the approach considering how the rest of the film plays out. (Someone breaks into the office and steals the leads, and the promotion instead becomes a whodunit.)

    Swipe to continue
    Use your keyboard arrows to navigate
  • 2 / 16
    Gordon Gekko (Wall Street)
    Michael Douglas in Wall Street

    Greed is good. With those three little words, director Oliver Stone's financial boogeyman Gordon Gekko (Michael Douglas) wormed his way into the lives of moviegoers everywhere. Said to be an amalgam of Stone, Dennis Levine, Owen Morrisey, Ivan Boesky, Asher Edelman, Michael Ovitz, Michael Milken, and oft-mentioned Trump endorser Carl Icahn, Gekko shows junior stockbroker Bud Fox (Charlie Sheen) the ropes during the Reagan era. Unfortunately for both men, those ropes include insider trading, which eventually attracts the attention of a much larger boogeyman — the federal government.

    Fox and Gekko's "friendship" is only as strong as what one can do for the other, and by the end of the film, Fox realizes that he has become too much like Gekko—a revelation that hits home when he realizes Gekko plans to buy Bluestar Airline at Fox's urging only to disband the company and put thousands — including Fox's own father — out of work. This leads Fox willingly into the waiting arms of the government where he plans to set Gekko up in exchange for a lighter sentence. Ultimately, it's hard to distinguish a good guy and a bad guy between the two men. Sure, Fox does the "right thing" in the end, but not before allowing himself to be corrupted by Gekko's influence. Gekko, for his part, teaches us that while there is a tremendous upside to lacking scruples in business, there are also vulnerabilities, like turning others against you and painting a target on your own back.

    Swipe to continue
    Use your keyboard arrows to navigate
  • 1 / 16
    Daniel Plainview (There Will Be Blood)
    Daniel Day Lewis in There Will Be Blood

    New Mexico prospector Daniel Plainview (Daniel Day-Lewis) strikes oil, causing the rest of his life to spiral out of control, all in the name of chasing the almighty dollar. Plainview does nothing altruistic without some sort of personal gain in mind, and is the very essence of what feng shui masters warn against when it comes to finding success, raping the earth of its resources in order to build a mansion with its own bowling alley.

    He is also not above murdering an adversary or two to get his way — something he demonstrates a few times during the film. He is a man without scruples or beliefs, and this manifests itself in the strained relationship that he has with his adopted son. His last act as a rich man, who seemingly has it all, is to needlessly force a preacher to denounce his faith in exchange for agreeing to purchase property from the man — an act he never actually plans on doing. Of course, you shouldn't feel badly for the preacher (played in a wonderfully sniveling way by the uber talented Paul Dano). He's a bit of a scumbag, too. But that's not the point. The point, again, is that greed can do nothing for you when your heart is as black as oil.


    There you go, business/movie geeks. Which of our picks do you agree/disagree with, and which ones should have been included? List your thoughts in the comments section.

    Swipe to continue
    Use your keyboard arrows to navigate
Swipe through the list Easily swipe through the list for a faster and better reading experience