Gordon Gekko got it wrong. Greed is for wimps. And lunch is good.

We've learned so much since 1987. Well, in some ways.

Twenty years ago next month, the stock market crashed—a great, bone-crunching, teeth-cracking dive, like when your Aunt Tilly has seven martinis and tries to get down the stairs. The YouTube generation probably can't comprehend the panic then.

On a single day, October 19, the Dow Jones industrial average dropped nearly 23 percent. The only worse one-day crash before or since came on December 12, 1914—after New York markets had been closed for six months because of World War I.

In '87, lots of people worried that America was in for the kind of multi-day meltdown that preceded the Great Depression. Thankfully, Guns 'N' Roses released Appetite for Destruction in 1987, or we all might've turned to Woody Guthrie records.

The '87 crash seems ridiculously long ago. Junk bonds were a new fad then and Ivan Boesky made millions as the world's greatest "arbitrageur," which sounded Gaul-ish and fancy until Boesky went to jail.

Drexel Burnham Lambert ruled financial markets from Beverly Hills and Mike Milken in '87 made $550 million-which sounded modern and enviable until Milken, too, went to jail.

The Dow broke through 2,000 in January; 2,500 in July. Such numbers worked like dopamine, sending investors into euphoria. Oliver Stone's Wall Street landed in theaters. Michael Douglas spoke for a generation of pinstriped, power-tied financial hawks when his Gordon Gekko character pronounced that greed is good and lunch is for wimps. We had a new hero for a new age.

And then, the reckoning. The crash seemed to turn the world around. Big things happened. Even if the 1987 crash wasn't a cause, it seemed like a marker.

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You want to talk about change? Talk to Stepan Pachikov, who in the past 20 years started technology companies Evernote and Paragraph. He now owns homes in Silicon Valley and New York. He used to live in Moscow, where Mikhail Gorbachev in 1987 tentatively unfurled glasnost. When Pachikov started a software company there a couple years later, it was still illegal to run a business.

"I didn't have any business life in 1987," Pachikov says. "I was listening to Voice of America and BBC through muffling stations—I am not sure I use the word properly. Who could imagine the largest Intel plant would be placed in China? Soviet Union doesn't exist anymore! Bulgaria is an EC country! Unbelievable!"

In 1987, IBM sold PS/2 computers ($1,350 without the optional hard drive that, today, could barely hold five MP3 songs) and Compaq sold a "portable" PC the size of an overnight suitcase.

The Internet was something used mainly by the kind of men who worked in labs and wore short-sleeve white dress shirts. Quantum Computer Services, founded in 1985, in 1987 changed its name to America Online, even though America was not even remotely online.

"At the time, I said a personal computer was an oxymoron, sort of like personal sex—you can do it but it's more fun if you're not on your own," says consultant and author Don Tapscott, who made his mark in the 1990s with Paradigm Shift: The New Promise of Information Technology. "We got a lot of resistance to the idea that networked computers would change the world."

Speaking of technological transformation, in 1987 Microsoft bought a little company called Forethought for all of $14 million. Forethought had just developed a piece of software called PowerPoint. That's right—before 1987, there was no PowerPoint. Today, it seems as though the entire American economy would collapse without it.

Ben Cohen in 1987 was helping business partner Jerry Greenfield run a blossoming little Vermont outfit called Ben & Jerry's. The pair was depicted as idealistic hippies for capping executive pay, investing in the community and giving some of the company's profits to charity.

Conventional wisdom said business was supposed to be run like a war. Wess Roberts in 1987 published the hugely successful Leadership Secrets of Attila the Hun, about how to manage like the famous fifth century plunderer.

"The words 'socially responsible business' were not well known," Cohen says. "It's amazing to look back, and in only 20 years, the idea of business having a larger responsibility to society has become mainstream."

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Google stresses ethics and responsibility. Bill Gates devotes his time and wealth to philanthropy. Salesforce.com dumps 1 percent of its equity into its foundation. And, these days, green is good.

Of course, some things have changed little since the '87 crash. You might not remember the international events that helped precipitate the market implosion.

On October 16, Iran hit a U.S. oil tanker off the coast of Kuwait with missiles. Early morning on the 19th, two U.S. Navy ships shelled an Iranian oil platform. Have a familiar ring? By the time the markets in New York opened, Middle East tensions had mixed with domestic economic concerns, and the potion melted the Dow like acid.

The crash was made worse by a new capability called program trading. Computers could watch stocks and indexes and trigger trades on their own! What a concept!

But only big guns like Goldman Sachs had the wherewithal to do it. For individual investors, the game suddenly felt rigged. How could a middle-class dad compete against arrays of microprocessors and tech wizards armed with algorithms?

Today, same thing. Dad may have a laptop that's as powerful as a whole 1987 Goldman trading room, but so what? Hedge funds hire complexity theory Ph.D.'s and run predictive software that could make Nostradamus look like an ignoramus. The investing game feels more rigged than ever.

All in all, makes you wonder if 2007 is a better place to be than 1987. Sure, the Cold War is gone, corporations are a bit nicer, and everyone's got email. Yet war looms, the economy teeters, real estate sags, and financial institutions have massive trading systems with hair triggers.

By the time you finish this essay, the Dow could crash again. October seems to be a popular month for such shenanigans.

Michael Douglas has said he wants to make a Wall Street sequel, but it couldn't be nearly as much fun as the original.

Twenty years down the line, jail time behind him, banned from the securities industry, an updated Gekko might be more like an idle retiree in Boca Raton. Lunch would probably be a highlight of his day. Point him to the buffet.