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Bill Gates’ 10 Most Memorable Moments

Microsoft’s cofounder says he’ll do charitable work after he retires this month. But we have some other suggestions: driving instructor, expert witness, and circus clown for starters. And Bill has experience in all of them.

(A version of this post originally appeared on

For more than 30 years he has roamed among us, a strange hybrid of Napoleon Dynamite and Vlad the Impaler. Nerdy yet ruthless, brilliant yet hobbled by blind spots regarding his company’s failings, Bill Gates leaves an indelible mark on everything digital. Yet on June 27, he’ll step down from his day-to-day duties at Microsoft to devote himself to philanthropic activities.

With snark in our hearts, we humbly offer the ten most memorable moments of Bill’s career, along with some suggestions for the career moves he should consider next.

1.Windows 95 Starts Up
August 24, 1995

We will probably never see another product launch like the one that propelled Windows 95 onto the world (and that’s probably a good thing). Even the iPhone debut last year paled in pomp and circumstance. The millions Microsoft paid for the rights to the Rolling Stones’ “Start Me Up” was only the beginning of the estimated $300 million marketing juggernaut that accompanied this launch. Among other excesses, the Empire State Building was bathed in Microsoft corporate colors and playing fields in Britain were painted with the Windows 95 logo so that it could be seen from the air. The Redmond campus was turned into a carnival for the day, with food, jugglers, clowns, hot air balloons, a ferris wheel and circus tents. And at the center of it was Bill – grinning awkwardly in his blue Microsoft polo shirt and trying to sound casual as he engaged in teleprompter banter with The Tonight Show’s Jay Leno.

Bill’s best line: “Windows 95 is so easy even a talk show host can figure it out.”

Good thing he didn’t quit his day job (until now).

Second career: Stand-up comic? Don’t call us, we’ll call you.

2. Bill Takes the Stand
August 27, 1998

Windows has always had problems with memory management; apparently Gates does too. Certainly that’s how it appeared when the CEO’s videotaped deposition in the United States v. Microsoft antitrust trial hit the Web. Gates’ reputation as a brilliant, detail-oriented control freak took a serious tumble as he peppered his testimony with “I don’t recall” (6 times), “I don’t remember” (14 times), and “I don’t know” (22 times). Gates quibbled about the meaning of words like “concerned” and “compete,” engaging US attorney David Boies in a circuitous dance of semantics that rivaled Abbott and Costello’s “Who’s on First?” routine for sheer loopiness. Excerpts from Gates’ video evoked chuckles from Judge Thomas Penfield Jackson. But Gates would have the last laugh when a US Court of Appeals overruled Jackson’s judgment against Microsoft three years later (see item #9).

Second career: Expert witness? We object.

3. Bill Gates: 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, purple 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 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.

[ More after the jump ]

4. A Gazillionaire Is Born

March 13, 1986

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

But instead of hording 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). Like every other tech stock, Microsoft’s share price plummeted after the bubble burst, further deflating his bank balance. Now with a personal net worth of just $58 billion, Gates is ranked 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.

5. Bill Gets Hitched

January 1, 1994

When you’re the world’s richest man you’re got to work double time to hide from the public eye. So when Gates decided to marry former Microsoft product manager Melinda French, he organized the wedding on the tiny Hawaiian island of Lanai, booked every hotel room on the island, and rented every helicopter in the state to frustrate potential paparazzi. The $1 million ceremony took place on the 12th tee of the Manele Bay Hotel golf course. On the guest list: Best man Steve Ballmer, Microsoft co-founder Paul Allen, Warren Buffet, and Washington Post doyenne Katherine Graham. The band? Singer Willie Nelson.

Second career: Wedding planner? We like Bill’s style, but it’s too rich for our blood. We’ll stick with J-Lo.

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 Noël “the Pieman” Godin took credit for the aerial pastry, one in a series of tart-fueled attacks Godin has inflicted on notable people. Gates is reported to have 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.

7. Turn On, Drop Out, Hack Code
January 1975

It was a photo of the MITS Altair 8800 on the cover of Popular Electronics magazine that started it all. After Harvard classmate Paul Allen showed him the issue, Gates called MITS president Ed Roberts and convinced him that he and Allen had created a BASIC program for the Altair, even though neither had written a single line of code. After Roberts expressed interest, they worked feverishly to create the program in eight weeks. Later that year Gates dropped out of Harvard and moved to Albuquerque, where he took a job writing software for Roberts at $10 an hour. Eventually he made enough money from the BASIC royalties to buy himself a Porsche 911 – and rack up multiple arrests for speeding and driving without a license.

Second career: Driving instructor? Thanks, but we’ll just walk.

8. Mr. Gates Builds His Dream House

1988 to 1995

What do you do when you have more money than God? Build a house fit for a deity, of course. Gates’ mansion on the shores of Lake Washington took seven years to complete and cost anywhere from $40 million to $100 million, depending on the source. According to Fortune Magazine, “It was a bachelor’s dream and a bride’s nightmare: 40,000 square feet with several garages, a trampoline room, an indoor pool, a theater with a popcorn machine, and enough software and high-tech displays to make a newlywed feel as though she were living inside a video game.”

After their wedding, Melinda apparently toned down some of the house’s boy-toyishness. Still, as PBS’s Robert X. Cringely reported, visitors to the home were asked to wear electronic badges that allowed the house “to adjust climate, music, lighting — even the electronic artwork on the walls — to match their preferences as they move from room to room. And what happens when more than one person is in a room? The reality of active badges is that Bill Gates is still king. When Bill is in the room, his taste rules.”

Second Career: Home builder? I think we’d rather just rent.

9. Microsoft Remains Intact
June 28, 2001

Bill & Co. dodged a major bullet when a Federal Appeals Court overruled Judge Thomas Penfield Jackson’s decision in US v. Microsoft, rescinding his order to split the company in two. The court found that Microsoft had indeed acted as a monopoly in bundling Internet Explorer with Windows, but ruled Jackson’s remedy too harsh. By then, Gates had already stepped down as Microsoft CEO, having handed the reins to Steve Ballmer in January 2000. Who knows? If Microsoft had been split, Gates might have found himself competing with his old college buddy Ballmer – and Yahoo might be trying to buy them instead.

Second career: Yahoo employee? That’s something we’d like to see.

10. Bill Gets His Sheepskin
June 7, 2007

More than 30 years after dropping out of Harvard, Bill finally got to flip his tassels. As a student Gates was known to prefer poker and programming over attending classes, but in June 2007 he received an honorary Doctor of Laws degree after delivering the commencement address at his alma mater. Also receiving an honorary law degree that day: former Celtics star Bill Russell. So it was a good day for Bills all around.

Remember kids, stay in school. And if you can’t manage that, starting your own software empire and dominating the world for 30 years isn’t a bad fall-back plan.

Second career: Career counselor? Hey, nobody knows more about second careers than Bill. He’s a natural.

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One Response to “Bill Gates’ 10 Most Memorable Moments”

  1. […] of tributes and memorials, some snarkier than others.  PC World’s Dan Tynan captured Gates’ 10 most memorable moments, including some he’d like to forget. Josh Quitner’s professional obit for Gates in Time […]