4. Bill Gates: PC World Centerfold Model (July 1987)

Yes, we are talking about that Bill Gates. No, he did not pose in the nude, praise Yahweh. He was wearing a dark blue suit, a lavender shirt, and a striped tie, instead of the usual lumpy sweater. And we are entirely to blame for this one because the Gates gatefold graced the July 1987 issue of PC World magazine, alongside an interview with the then-32-year-old software tycoon. It was the first centerfold the magazine ran, as well as (almost certainly) the last. Hey, we were all young and stupid in those days.

Second Career: Pin-up boy? Sure--the day after we all go blind.

5. A Gazillionaire Is Born (March 13, 1986)

The day Microsoft went public, Gates became an instant megamillionaire (actually a $234-millionaire, based on the IPO price). But it wasn't until July 17, 1995, that Forbes magazine named him the richest featherless biped on the planet, with a net worth just shy of $13 billion. His wealth snowballed from there. During the height of dot-com madness, Gates' paper fortune exceeded $100 billion, inspiring several Web sites devoted to measuring just how much money that was in real terms. No wonder people found it easy to believe the rumor that he'd give you $1000 just for responding to an e-mail (a classic Net hoax).

But instead of hoarding all the cash, Gates put his money where other people's mouths are, establishing the William H. Gates III Foundation (later changed to the Bill and Melinda Gates Foundation). After the bubble burst, Microsoft's share price plummeted (as did every other tech stock), further deflating his bank balance. Now with a personal net worth of just $58 billion, Gates ranks third in the world behind Mexican telecom entrepreneur Carlos Slim Helu and Bill's bridge-playing buddy, Warren Buffet.

Second Career: Quasi-retired philanthropist? This one he's got down cold.

6. If It's Cream Pie, This Must Be Belgium (February 4, 1998)

Gates was notorious for making pie-in-the-sky predictions for Microsoft products. So it probably shouldn't have surprised him to receive a pie in the eye when he visited Brussels in February 1998. Gates got creamed as he was entering the Concert Noble Hall for an education conference sponsored by the Flemish government. Belgian anarchist Noel "the Pieman" Godin took credit for the aerial pastry, one in a series of tart-fueled attacks Godin has inflicted on notable people. Gates reportedly said later that the pie "wasn't that tasty."

Second Career: Circus clown? Hey, Gates takes a pie in the face as well as Soupy Sales ever did. We think he has potential.

(Thanks to Belgian TV station een for the photo.)