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Sep 2, 2010
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Wall Street: Money Never Sleeps marks the return of corporate headhunter Gordon Gekko, 23 years older and heading back into Wall Street en route the 2008 financial crisis. The film stars Michael Douglas, Shia Lebouf, Carrie Mulligan and Josh Brolin.
After a lengthy stint in prison, Gordon makes an attempt to revitalize the stock market before it crashes and reconnect with Winnie with the help of Jacob, his daughter’s fiancé.

They are also out to spark revenge on the man his newfound apprentice blames for his mentor’s death. But given how anti-trustworthy Gekko is, we’re sensing a bit of an awesome twist here.

Playing a toned down anti-hero this time around could work just as well for Michael Douglas, whose Gordon Gekko character remains to be one of the most iconic villains we’ve ever seen on screen.

So iconic is Gordon Gekko, that he joins the ranks of an Italian mafia boss, an Irish gangster and the rest of the coolest evil mentors in cinema. Find out who they are, starting off with Mr. Wall Street himself:

Gordon Gekko   
Played by Michael Douglas in Wallstreet (1987)       

Gordon Gekko is a spectator to the point of psychology, treats suits as guinea pigs and the corporate world as his laboratory. The man has purposely influenced Bud Fox to believe that greed is good, and together they played everyone in their Wallstreet game.Gordon was named the fourth richest fictional character by Forbes, with $8.5 billion to his name. Naughty rich.

Senior Swag Line: “You see that building? I bought that building ten years ago. My first real estate deal. Sold it two years later, made an $800,000 profit. It was better than sex. At the time I thought that was all the money in the world. Now it's a day's pay.”

Next: Paying our respects to the mafia boss