Can Alex Bogusky Help Microsoft Beat Apple?

Enlarge"To try to be cool is to not be cool," says Andrew Keller, left, with Rob Reilly, Crispin's co-executive creative directors | photographs by Peter Yang

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"He looked like Jesus," confesses a blushing 27-year-old hipster in gray New Balance sneakers and a zip-up hoodie. She is talking about her boss, Alex Bogusky, the man who has built arguably the hottest ad agency in the country, Crispin Porter + Bogusky. And she is trying to make herself heard over the din of conversation at the New Denver Ad Club, where

500 locals have gathered to hear him speak. Bogusky had only recently moved to town after hauling half of his now 700-person operation from Miami to nearby Boulder. "Just the other day, I was walking by the kitchen in the office," says the young art director, two years into working for Bogusky. "There was, like, this halo over him."

On this breezy evening in April 2007, six-packs of Molson and the greasy scent of Burger King burgers -- two brands revived by Crispin -- give the chandeliered concert hall a calculated shot of the lowbrow. In a few moments, the khaki-and-blazer crowd will see the legend live, on stage, where he will share such intimacies as "I once farted on production for a Gap spot" and "Life is a pyramid scheme." Until then, the anticipation is thick. "It's kind of like having a major stage production coming to your small town," says one adman with Frank Sinatra hair. "Like the circus." Another whispers, "I can't wait to hear this guy from Crispin Glover!"

For nearly a decade, the unhip have flocked to Bogusky in the hope that a little of his mystique might rub off. There is no more adept a mechanic of cool, and Bogusky can give it -- and take it away. In 1998, he helped strip the sexy gloss from cigarette smoking with his raw, award-winning "Truth" campaign. In 2001, he subverted the SUV and Hummer fad by getting consumers to embrace "tiny" with his media-bending stunts for the Mini Cooper. More recently, he resurrected Burger King's 1960's-era "King" character, turning it into an unlikely icon, which has since done everything from date reality-TV pinup Brooke Burke to appear in his own Xbox video game that has sold 3.5 million copies.

Bogusky is famous for pushing clients to the edge. His TV work for Volkswagen included a close-up of a horrific, fatal-seeming car crash; for Orville Redenbacher, he called the deceased popcorn pitchman back from the dead; for Virgin Atlantic's business travelers, Bogusky offered up mock porn on a hotel TV network. "What Crispin has been able to do consistently is not just produce breakthrough work, but actually create new audiences for brands," says Mary Warlick, who runs the One Club, which awards creative excellence in advertising.

Now Crispin has been handed perhaps its biggest challenge to date: Microsoft. The tech giant stunned the ad world in March when it passed over safer choices like Fallon, JWT, and its agency of record, McCann Worldgroup, and awarded its new $300 million consumer-branding campaign to Crispin. It was an act of courage or desperation, depending on whom you ask. Over the past couple of years, Microsoft's already problematic reputation in some circles -- as the soulless, power-hungry purveyor of lackluster products -- has suffered a series of self-inflicted wounds. It spent two years and $500 million on the media blitz around the long-delayed Windows Vista launch, only to see the January 2007 "Wow" campaign, which likened Microsoft's new operating system to Woodstock and the fall of the Berlin Wall, derided as arrogant and creatively void. Vista itself sold poorly, leading to price cuts of up to 40%. Worst of all, the flop bred a new generation of Microsoft haters. "Microsoft has really lost control of its image," says Rob Enderle, an influential advisory analyst for tech companies including Dell, HP, and Microsoft. And with its two most formidable competitors -- Apple and Google -- boasting their own consumer cults, that's the last thing Microsoft can afford to do.

Nothing is doing more to carve away at Microsoft's reputation -- and contribute to its loss of market share -- than the assault launched by Apple two years ago in the form of the "Mac vs. PC" spots featuring The Daily Show satirist John Hodgman. The ads became immediate pop-culture fixtures, spawning more than 1,000 video spoofs on YouTube and taking home last year's Grand Effie, the ad industry's highest honor for effectiveness. "Nobody messes with anyone in the tech industry the way Apple has messed with Microsoft," says Enderle. "It's the first time I've ever seen a major national campaign that disparages a competitor, and the competitor just sits back and takes it. If somebody tried to do that to Oracle, you wouldn't be able to find the body." Gartner media research analyst Andrew Frank credits Apple -- whose annual media spend is less than half of Microsoft's nearly $1 billion budget -- with single-handedly rebranding Microsoft "as a kind of self-conscious and self-absorbed nerd that is out of touch with the normal lives and needs of its users."