Crime, it's been said, doesn't pay. It can, however, make for some fairly iconic images. The celebrity mugshot has long been the holy grail of celebrity photography, because, in a strange way, it represents the famous at their most human—the lighting is unflattering, the makeup non-existent (unless, of course, you're Paris Hilton), and the timing, well, there are few moments in people's lives less opportune than when they are arrested.
We've combed the archives to pull together some of the best mugshots from the world of technology. It's a list that includes some disgraced corporate execs, a notorious spam king, a genius young hacker, and a future billionaire philanthropist, among others. The pictures, like the crimes, run the gamut, with expressions of confusion, fear, and, in some cases, downright elation.
1.
Bernard Ebbers
In honor of Bernie Madoff's fraud hearings, Time Magazine compiled a list of the most crooked CEOs. This former WorldCom chief rounded out the top ten (actually moving up a spot, after charges were thrown out for another entrant), thanks to his attempts to cover up massive corporate debts. WorldCom filed for bankruptcy and its then CEO Bernard Ebbers was sentenced to 25 years in a Louisiana prison.
2.
Mark Swartz
Another sad tale of a corporate executive gone wild, Tyco's chief financial officer also got sentenced to 25 years. Sadly, Swartz is lacking his curly locks in this shot, due to the prison's shaved head policy. Swartz was sentenced along with CEO Dennis Kozlowski (who also has a pretty menacing looking prison shot), after being accused of stealing more than $150 million.
3.
Julian Assange
Granted, this one isn't really a mugshot. It's actually a wanted poster—which perhaps goes a ways toward explaining why he doesn't have that generally disheveled just-arrested glow of so many of the others on this list. Interpol released the image late last year, when it placed Julian Assange on its most wanted list—what the organization calls "red notice." Assange was placed on the list not because of Wikileaks activities, but rather for rape and molestation charges stemming from a trip to Sweden. The embattled former hacker eventually turned himself into British authorities, where he faced trial for extradition—a court battle he ultimately lost.
4.
David L. Smith
Say what you will about David L. Smith, the man knows how to name a virus. As discussed in our recent malware timeline feature, the creator of the Melissa virus named that nasty little bit of malware after a Floridian lap dancer. After all that, judging from this shot, Smith seems pretty happy with himself.
5.
Jeremy Jaynes
Back in 2004, Jeremy Jaynes became the first person convicted of felony spam. Jaynes was tried under Virginia's tough anti-spam laws, due to the fact that he was using servers in that state to help send out massive volumes of junk mail. The spam moves into felony territory if e-mails are sent to more than 10,000 addresses in 24 hours. Prosecutors told the court that Jaynes made almost $24 million with his spamming scheme. Ultimately, however, Jaynes' conviction was overturned, after it was determined that the law violated his first amendment rights.
6.
Bill Gates
Easily one of the best known mugshots of the 20th century, this goofy classic was captured after the future billionaire was arrested for a traffic violation in New Mexico in 1977 (two years after the founding of Microsoft). The precise details of the arrest have been lost to history, but it's worth pointing out just how chipper Gates looks in the head-on shot. If he did have any misgivings about the arrest back then, he's clearly come to peace with them in the intervening 30 years—the iconic shot showed up as a prop drivers license in one of those 2005 Jerry Seinfeld Microsoft commercials.
7.
Kevin Mitnick
In 1979, a 16-year-old Kevin Mitnick had hacked his way into his first computer network. Before it was all over, he would be accused of hacking into Motorola, Sun, Fujitsu, NEC, Nokia, Pacific Bell, the FBI, and the Pentagon. Mitnick would go on to serve five years, including eight months in solitary. After being freed in 2000, Mitnick went on the straight and narrow, opening up the security firm Mitnick Security Consulting LLC.
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Brian Heater has worked at a number of tech pubs, including Engadget, Laptop, and PCMag (where he served as Senior Editor). Most recently, he was as the Managing Editor of TechTimes.com. His writing has appeared in Spin, Wired, Playboy, Entertainment Weekly, The Onion, Boing Boing, Publishers Weekly, The Daily Beast and various other publications. He hosts the weekly Boing Boing interview podcast RiYL, has appeared as a regular NPR contributor and shares his Queens apartment with a rabbit named Lucy.
