Smile When You Say ThatSmile When You Say That

Pop culture has often been unkind to people who work with computers. In the 1980s, the popular stereotype of a buffoon with taped-up glasses, ill-fitting pants, and a cowlick appeared in movies like Revenge of the Nerds. In the 1990s, they became villains (though generally better dressed), hacking into our home PCs and destroying Sandra Bullock's life in The Net. In the new century, Saturday Night Live cast member Jimmy Fallon created a recurring character called "Nick Burns, Your Company's Computer Guy." He's a surly, superior lout, answering users' requests for support with insults and invective.

But increasingly, the world of information technology is starting to turn cool. The jokes are told by and for the geek, rather than about him.

The most famous example of this sort of humor is probably Dilbert, the mouthless engineer who began in creator Scott Adams' daily comic strip, and boomed into television, books, and more merchandise than even Dogbert could imagine.

Drawing Conclusions
But Dilbert, all his geekiness aside, was really more about office life than technology itself. A better representative of the IT world is User Friendly, a Web-based cartoon that follows the adventures of the folks at fictitious Internet service provider, Columbia Internet.

User Friendly is drawn by "Iliad," the pen name of 33-year-old J.D. Frazer. While working at an ISP in Canada, Frazer's doodles caught on in the office, and he started posting them on a Web site.

What sets User Friendly apart from Dilbert and other daily strips is its proud embrace of hard-core geek jokes that most people wouldn't get: operating-system puns, server gags, and punch lines based on Linux commands.

In one recent story line, Chinese spies stealing U.S. technology were thwarted by Clippy, the ever-annoying paperclip "assistant" in Microsoft Office. Another had a tech-support worker deal with a caller's familial woes:

That esoteric approach proved to be a recipe for success. User Friendly is now User Friendly Media Inc., a publicly traded, booming business, complete with half a million unique viewers a month, three books, corporate partnerships, and armies of devoted fans.

(User Friendly isn't the only online computer-centric comic strip: If you're looking for counter-productivity tools, also check out The Joy of Tech, Kevin and Kell, and The VC.)

User Surly
Friendliness isn't the only thing that sells IT humor. Comedian Matt Besser, formerly a star of Comedy Central's sketch comedy show The Upright Citizens Brigade, has perfected a much more cutting brand of comedy that is sure to appeal to the hidden impulses of IT staff everywhere.

During the peak of the dot-com boom, Besser started getting phone calls in his Manhattan apartment that were intended for the technical support line of a free Internet service. When the users neglected to dial a "1" before entering the area code, they got Besser instead of the real support line. At first, he was nice to the callers, but when the phone kept ringing, night after night, he started lashing out.

The result is an album of surreptitiously recorded calls that fulfill the dark fantasies of every person who's ever worked a tech support line. Besser does what real IT people can't: harass callers, put down morons, and generally work out all the frustrations of dealing with other people's computer problems.

On one track, Besser confronts a caller with pure obstinateness:

On another, he segues from innocent questions about the user's computer to wilder fare:

The album, May I Help You [Dumbass]? is pure schadenfreude. Besser is complementing its release by performing a one-man show in limited engagements around the country, where he plays the recordings and vents other frustrations.

Dot Comedy
Another currently touring act isn't about IT itself, but rather the working environment that so many tech workers have come to know and love (or loathe): the dot-com.

When Mike Daisey worked for Amazon.com from 1998 to 2000, the boom years, he swallowed the promise of the dot-com revolution hook, line, and sinker. No longer with the company, and with his non-disclosure agreement recently expired, Daisey has put together a one-man show that describes his love/hate relationship with the startup environment.

At one point, he discourses on the bizarre interior design tendencies of the IT world.

"I don't know what it is about tech companies and their love for exposed duct work, but it's ubiquitous," he says. "Everyone needs to expose their duct work as if to say, 'Man, we are so busy ... we are so busy that we haven't even covered up these ducts.'"

Later, he reads from a letter he wrote to founder Jeff Bezos:

Revenge of the nerds, indeed.

Daisey's show, entitled 21 Dog Years: Doing Time @ Amazon.com, is currently being performed in New York through Aug. 23. It's also available for viewing in its entirety on his Web site.

Matt Besser's album May I Help You [Dumbass]? is for sale online. His one-man show is running in Hollywood through the end of August, and will move to Chicago in early September. More details are on the Web site.