Big Risk on the Big Screen

The very best movie plots are the ones driven by the excruciating tension that comes when characters take risks—calculated or otherwise—and then struggle to overcome them…

The Matrix

1995 – Keanu Reeves, Laurence Fishburne
Morpheus: “This is your last chance. After this, there is no turning back. You take the blue pill—the story ends, you wake up in your bed and believe whatever you want to believe. You take the red pill—you stay in Wonderland and I show you how deep the rabbit-hole goes.”

Wall street

1987 – Michael Douglas
Gordon Gekko: “I don’t throw darts at a board. I bet on sure things. Read Sun-tzu, The Art of War. Every battle is won before it is ever fought.”

Heat

1995 – Al Pacino, Robert DeNiro
Neil McCauley: “He knew the risks, he didn’t have to be there. It rains… you get wet.”

Dirty Harry

1971 – Clint Eastwood
Harry Callahan: “I know what you’re thinking: ‘Did he fire six shots or only five?’ Well, to tell you the truth, in all this excitement, I’ve kinda lost track myself. But being this is a .44 Magnum, the most powerful handgun in the world, and would blow your head clean off, you’ve got to ask yourself one question: ‘Do I feel lucky?’ Well, do you, punk?”

Arbitrage

2012 – Richard Gere, Susan Sarandon
Syd Felder: “What’s baffling to me, despite your sentimental history together, is why you would put your family’s future in this kid’s hands.”
Robert Miller: “He’s not like us.”
Syd Felder: “Is that a good thing?”

Casino Royale

2006 – Judi Dench
M: “I knew it was too early to promote you.”
James Bond: “Well, I understand double 0’s have a very short life expectancy… so your mistake will be short-lived.”

Risky Business

1983 – Tom Cruise
Miles: “Joel, you wanna know something? Every now and then say, ‘What the f***.’ ‘What the f***’ gives you freedom. Freedom brings opportunity. Opportunity makes your future.”

Literary Risk-takers We Love

Our collective fascination with characters who encounter—and sometime even provoke—risk, is deeply ingrained. Through the ages, there remains something compelling about stories that detail the travails and tribulations of others. Maybe it’s because we all know that truth is always stranger than even the best fiction. A random walk through the evidence:

ROMEO & JULIET

1595 – William Shakespeare
An emotional steeplechase of family beef, possessive cousins, enabling nursemaids, and a meddling Friar. It was a risky proposition from the start, but who has ever been able to talk sense to a teenager?

Jack and the Beanstalk

Old English Fairytale
Jack buys some magic beans, shinnies up the stalk, sneaks into a giant’s castle in the sky, and steals his treasure. He repeats this high-risk strategy three times, nabbing gold coins, a goose that lays golden eggs and, finally, a harp that plays itself. Today, he’d definitely be running a private equity fund.

Alice in Wonderland

1865 – Lewis Carroll
For a proper Victorian maiden in a pinafore, Alice is actually a modern bad-ass. Her adventure is fraught with risk and danger from the start: the beastly Duchess, the Cheshire Cat, the hookah-smoking caterpillar, the Mad Hatter and the March Hare and, of course, the Red Queen. Every decent tea party has a Dormouse who needs to be stuffed into a teapot (you know who you are). And who among us hasn’t treaded water in a pool of tears at some point in our adult lives? Conversation with a mouse, optional.

Harry Potter and the Philosopher’s Stone

1997 – J.K. Rowling
Harry Potter is a beleaguered orphan who slowly comes to terms with his special powers only to be confronted with a wily nemesis, Lord Voldemort, and his assorted henchpersons. Is there a greater bore than an aspiring immortal?

The Hobbit

1937 – J.R.R. Tolkien
Mild-mannered hobbit, Bilbo Baggins, reluctantly braves wizards, wolves, trolls, dwarves, elves, goblins and Gollum to settle a score with an irritable dragon (is there any other kind?), gain riches and snag a golden ring that is the obsession of a deeply disturbed cave-dweller with a penchant for riddles. For most of us, it’s just another day at the office…