Filling in the holes: City Council candidates Jay "Boss" Rubin (top) and Tres Shannon.

Hey, it could happen—Voodoo co-owner Tres Shannon and fryer Jay "Boss" Rubin have filed to run for the two seats up for grabs this May 16 on the five-member council.

Both aim to take advantage of new city campaign-finance laws that would let them collect $150,000 in public money if—and it's a big if—each gets $5 donations from 1,000 people.

Shannon, 40, who ran unsuccessfully for mayor in 1994 and city commissioner in 1996, predicts he could probably get the support for his challenge to Commissioner Dan Saltzman in one night.

And maybe he can—between his posts at the popular Old Town late-night spot Voodoo, the short-lived but über-hip X-Ray Cafe, and his renowned karaoke and DJ performances, Shannon is a nightlife guru in Portland.

Rubin is less confident about finding so many supporters for his run against Commissioner Erik Sten, but says, "The point is to participate."

Rubin, 23, brings a passion that has translated before into the Portland Challenge, an annual group swim across the Willamette to raise money for an orphanage in Tanzania. (Full disclosure: Rubin has persuaded WW to run free ads for that fundraiser, and his mother, ages ago, was a WW freelancer.)

Rubin also teaches Swahili classes on Monday nights at the doughnut shop.

Both halves of the doughnut duo say they're interested in halting the strip-mall takeover of downtown Portland and making the city's current infrastructure work more efficiently.

But if either or both gets elected, don't expect maple bars to fall from the sky—they're not running on a doughnut ticket. "This is a serious bid for City Council," says Shannon.