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 ten of the most memorable moments of Bill's career, with suggestions for suitable career moves he might consider if he decides to follow the logical path indicated by each milestone.

1. Windows 95 Starts Up (August 24, 1995)

We'll probably never see another product launch like the one that propelled Windows 95 onto the world (and that's surely a good thing). Even the pomp and circumstance surrounding the iPhone's debut last year paled in comparison. The millions of dollars that 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 to make it visible from the air. The Redmond, Washington, campus of Microsoft was transformed 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 all 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. 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 his BASIC royalties to buy himself a Porsche 911--with which he racked up multiple arrests for speeding and driving without a license. 

Second Career: Driving instructor? Thanks, but we'll just walk.

3. Bill Takes the Stand in Antitrust Case (August 27, 1998)

Windows has always had problems with memory management; evidently Gates does too. That's certainly 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 U.S. 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 U.S. Court of Appeals overruled Jackson's judgment against Microsoft three years later (see item #9).

Second Career: Expert witness? We object.

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's 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.