Would Bernie Madoff make a great movie villain? Maybe, if, say, Robert De Niro played him, with a cool catch phrase: “The only difference between a Ponzi scheme and a great investment model is the jail sentence…” or something like that. But in print or on the six o’clock news, Bernie’s more reviling than interesting. There’s nothing absorbing about someone who steals from Eli Wiesel’s charity or fleeces grandmothers out of their life savings.

But on the screen or in books we adore our Wall Street super-villains. They appear impenetrable and invincible with delightfully underhanded characteristics: When they steal someone’s money they offer to help their victims look for it; they have strong wives and very sexy girlfriends; they speak in sound bites, “Greed is good”; they surround themselves with scapegoats and disposable people like friends and family; they always keep lying, even when everyone knows they’re lying, “I didn’t do it!”; they act like the devil but dress like an angel. All of which makes the inevitable crash in the third act just as fun to watch as the climb in the first two.

The thing about Wall Street villains though, either real or imagined, is they don’t have staying power in popular culture. With the exception of Gordon Gekko, who lives on in infamy, and perhaps Bernie Madoff who was so much of a louse it’s hard to forget him, the rest of the crooked French cuff crowd disappear like smoke from a Cohiba. And as time goes on, these great liars become the answers to the “What ever happen to?” questions.

And so, in the interest of preserving the financial rogue’s gallery for posterity, below is my top ten list:
#10 – Kenneth Lay. Enron’s Smartest Guys in the Room is part of the Mt. Rushmore of corporate greed and under handling. R.I.P.
 
#9 – Sam Israel. He has issues. Guy Lawson, in his book Octopus, brings Israel’s utter insanity to vivid life. He was a bad boy. He may have scored higher on his VQ (Villain Quotient) if you didn’t feel so bad for him. While reading this compelling story you aren’t sure if he’s crazy or crazy smart. I still don’t know. But having faked a suicide, initiated a nationwide manhunt, embroiled in a secret shadow bond market and enlisting a former black-ops intelligence operative as his wingman – you’re a lock for the top ten villain list.

#8 – Nick Leeson. No villain list is complete without a dastardly Brit. Leeson’s memoir and the movie based on it both called Rogue Trader tell the tale of fraudulent and reckless speculative trading that bankrupts England’s oldest banking establishment. And he did all this by the time he was 28! It’s like a Wall Street version of the Children of the Corn. Ewan McGregor plays a Leeson on screen.

#7 – Jordan Belfort, The Wolf of Wall Street, who lied, stole and cheated his way to make millions on a daily basis at the firm Stratton Oakmont in the 90s. Scorsese and DiCaprio are bringing his story to the big screen. This will be one of those rare occurrences when the movie is better than the book.

#6 – The Duke Brothers, Randolph and Mortimer, in Trading Places make a wager in the “usual amount,” to settle a dispute on nature versus nurture. Laughing the whole way through, in the end we discover after all of the elaborate lengths they go to conduct their experiment that the “usual amount” is $1.

#5 – Greg Weinstein, the boss from hell in the movie Boiler Room is played by Nicky Katt: “We don’t sell stock to women. I don’t care who it is, we don’t do it. Nancy Sinatra calls, you tell her you’re sorry. They’re a constant pain in the ass and you’re never going to hear the end of it alright? They’re going to call you every fucking day wanting to know why the stock is dropping and God forbid the stock should go up, you’re going to hear from them every fucking 15 minutes. It’s just not worth it, don’t pitch the bitch.” And, “Don’t you have a canoli you can stick in your mouth?” A chauvinist or misogynist and evil son of a bitch, Nicky Katt’a portrayal makes you love to hate him.
dont pitch the bitch

#4 – Let’s see… Richard Miller (Richard Gere) in Arbitrage has it all: financial fraud, adultery, manslaughter, leaving the scene of an accident, cooking the books to sell his company and calling his young African American friend who is trying to live an honest life and making him an accomplice. And he gets away with it all… or does he?

#3 – Den of Thieves three-headed monster – Financiers, bankers and lawyers—oh my! Except in this story there’s no Dorothy. James B. Stewart’s non-fiction best-selling work fascinates the insider trading scandals of the 1980’s. Names like Milken, Boesky and Levine, which once held household status, have gone from inmates to their photos on the back of milk cartons.

#2 – “Fuck Warren Buffett,” says Dick Fuld played by James Woods in Too Big To Fail. Those are some fight’n words. There are a few people you never take shots at: Jesus, Shakespeare, Eminem and Warren Buffett. Woods played Fuld brilliantly. He makes you forget about the investors and employees of Lehman Brothers. Early on we learn of Fuld’s biggest weakness, he doesn’t know how to negotiate from a place of weakness–fun to watch. And the irony of his first name is lost on no one.
 
 

#1 – Patrick Bateman, the American Psycho. Stereotypes on steroids. Wall Street during the late 80s boom filled with sex and violence mixed with postmodern literature lands at number one. Bret Easton Ellis created a god. Bateman is insecurely insane or insanely insecure, it doesn’t matter.

Sorry Gordon Gekko professionals don’t count.

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