Coming Zune

"Wicked!" exclaims Richard Winn, as he stands on Seattle Center's Broad Street Lawn during Bumbershoot, expressing appreciation for the French band Nouvelle Vague. "That's weird. I got goose bumps." He pulls up the sleeve of his blue sweat jacket to prove it.

The bubbly 42-year-old British expatriate is so much of a fanatic that he knows not only that "Love Will Tear Us Apart," the song the band is covering, was first released in 1980 by Joy Division, but what was on the B-side ("These Days"). No wonder: Winn has spent his entire adult life in the music business, first making tea for UB40 in a Birmingham, England, recording studio before eventually moving to Los Angeles, where among various marketing and producing gigs he worked for Japanese rock star Yoshiki.

On this breezy end-of-summer evening, though, Winn is here on behalf of his new employer, Microsoft. He's part of the team that, on Thursday, Sept. 14, plans to show the press the Redmond company's answer to Apple's fantastically popular iPod. Winn is head of artistic development for Microsoft's new device, dubbed Zune. His sortie is to integrate the device with the music scene, in part by promoting emerging artists, so he's been checking out music venues like mad since he moved to the area two and a half months ago.

Microsoft hopes that its emphasis on the music, rather than just the gadget, will help set Zune apart from its dominant rival. The company is also loading Zune with a 50 percent larger screen than current iPods, as well as wireless capabilities that will allow users to send their favorite songs to other users with devices in close proximity.

Yet even as Microsoft gets ready to release Zune in time for the holiday season, Apple is grabbing attention with reports that it is about to offer downloadable movies that can be played on a new version of iPod with a bigger screen. Microsoft says that Zune will be compatible with video formatted for an iPod or any other media player. But the company is focusing on music, which it believes makes more sense for a device that people use while jogging or riding their bikes. Still, even in the music space, Microsoft has its work cut out.

"This device, in my opinion, is make or break," says Seattle author Charles Cross, whose books include a memoir of Jimi Hendrix. Cross notes that iPod has captured 75 percent of the music-player market in the U.S. It has done so by forcefully laying claim to that elusive quality of cool—offering not only the ability to digitally access music, but also a sleekness of design that has made the device a fashion accessory.

There was a moment in the early '90s when Microsoft was cool, too. Software was king and Microsoft was the king of software. But then the dot-com bubble burst, and the company lost ground, as rivals like Apple began producing sexier products. Witness the reaction of Nick Harmer, bassist for the ascendant local band Death Cab for Cutie, on Microsoft's musical foray.

"I guess I'm a little skeptical," he says. A lot of that has to do with Windows, Microsoft's signature product. "It's clunky, aesthetically not interesting," Harmer says of the software. "It's the reason why I switched from a PC to a Mac."

In its quest to catch up to iPod, however, Microsoft has hired an army of musical savants. Like Winn, many on the Zune team come from recording labels, radio stations, or other music companies. They include KEXP DJ Kyle "Kid Hops" Hopkins and Chris Stephenson, another British expat who worked as an MTV vice president in Europe and as marketing head for House of Blues, the L.A.-based chain of clubs and concert spaces.

The visionary behind Zune, however, is a native Microsoftie—J. Allard—probably the one man at the company whose hipster credentials are unassailable.

Bearing a shaved head, an athletic build, and a taste for the jackets of edgy fashion designer Mark Ecko, the 37-year-old Allard came to Microsoft in 1991 after graduating from Boston University, where somewhere along the line, "James" was reduced to simply "J." Allard's early claim to fame came soon after he arrived on the company's Redmond campus, during perhaps the first period when Microsoft found itself lagging behind the technological curve. Other companies were starting to capitalize on the potential of the Internet, a platform that Microsoft seemed only dimly aware of. Having come to Microsoft with what he says was the aim of getting his mom on the Internet, the then-24-year-old cranked out a 20-page wake-up call of a memo. Originally sent to his direct supervisors, the memo made its way into the hands of Bill Gates. "It got around," Allard says.

Plugging away on the Internet for seven more years, Allard longed for a change. He took three months off and bought a bunch of techie toys, including a Sony PlayStation and a portable music player. It's easy to picture Allard happily messing around with his toys: He's got a reputation as a driven competitor, but he also evinces puppy-dog playfulness. When the photographer at a promotional shoot at Belltown's Rendezvous nightclub asks him to do a foot motion for an artsy shot of his black-and-white Nikes, he doesn't hesitate. "I can do a toe curl," he volunteers. Minutes later, he's jumping off the stage.