Oregon restaurateur Michael Hebberoy is determined to challenge assumptions about food and spirits. Writer Bill Donahue gets an earful of ideology—and some delicious meals.

"Why can't gin be something you drink in front of a fire at a ski lodge? Why can't it be grounded and ruminative and spicy?" asks Portland, Oregon, restaurateur Michael Hebberoy. Just 29, with blond hair and the delicate features of a boy, Hebberoy has made a life's work out of flouting culinary convention. In March he will launch what may be the world's first line of seasonal gins, which he created with Medoyeff Vodka, an artisanal distillery in Portland. He'll start by introducing the herbaceous GBT Summer Gin—named after his gastropub Gotham Bldg Tavern—at top restaurants across the nation. Then, in the fall, he will unveil GBT Winter Gin, flavored with black tea, dried cranberries and carob root.

The gins are just another unorthodox idea from a young rebel, a real estate developer's son who began his career four years ago, bent on changing the way Americans think about food, wine and spirits. In 2001, Hebberoy and his wife, Naomi, a chef, opened an illegal restaurant they called Family Supper in their rented Portland bungalow. Sans business license, the Hebberoys fed friends and friends of friends by invitation only. The meals, all served family-style, cost at most $20 a person, paid on the honor system. The 20 or so chairs were mismatched, the carpet was a shabby white shag, and the whole thing exuded such outré charm that the Hebberoys soon became the It couple of Portland's avant-garde dining scene. In 2002, reluctantly licensed, they moved Family Supper into a commercial space where today 40 or so strangers pass earthenware platters down long wooden tables. There is one set three-course menu each night, with dishes like braised lamb shoulder with roasted broccoli and squash.

Soon, the enterprise grew into a mini empire. When chef Morgan Brownlow moved to Portland from Oakland, California, where he'd been working under Paul Bertolli at Oliveto, he instinctively sought out the Hebberoys. Brownlow immediately became a cook at Family Supper, stayed for a year, then went on to stints at other restaurants. He took a hiatus and, lacking a job, threatened to leave town. "We opened Clarklewis," Hebberoy says, "basically to keep Morgan in Portland. We didn't want to stop eating his food." The Hebberoys built Clarklewis on a 1910 loading dock amid a maze of train tracks several blocks from the nearest developed neighborhood. Now, candles flicker in the semidarkness of the dining room as the kitchen butchers its meat in-house and serves dishes that look as though they're straight out of a Brueghel painting. Pork cutlets, sliced from a whole hog that hangs in the kitchen, are layered with sage and prosciutto and then pan-fried. Instead of offering a prix fixe or tasting menu, Brownlow creates a looser vibe: "if you don't want to make any decisions at all..." the menu reads, "morgan will cook three or more courses for you for thirty-five dollars...enjoy."

The Oregonian newspaper named Clarklewis Restaurant of the Year even before its interior was completed, and the Hebberoys capitalized on their success by opening the Gotham Bldg Tavern last year. A honeycomb of giant fir beams separates Gotham's bar from its dining room; in the front waiting area is a cozy library with books for diners to thumb through. Chef Tommy Habetz, who had worked with Mario Batali in New York City, prepares dishes like Manila clams cooked with sweet vermouth and hot soppressata.

Hebberoy takes the food at all the restaurants very seriously. Not only are a majority of the ingredients carefully sourced from local organic farms, but Hebberoy turns his waiters as well as his kitchen staff into culinary experts. Everyone is strongly encouraged to participate, unpaid, in a training field trip each month, learning how to forage for native plants, say, or to make chocolate from scratch. "When you order wine," Hebberoy boasts, "there's a good chance that your waiter has picked the very variety of grapes that he's serving."

Hebberoy says his food philosophy is shaped by the DIY arts movement, which has brought us renegades like punk pioneers the Clash and painter Keith Haring. He's not afraid to make controversial statements that others would contend are patently untrue. "I just think there's a lot wrong with food culture," he says. "It's sterile. It's based on a lot of dusty assumptions, like excellent food can only happen in restaurants you pay $150 to eat in. People say that Alice Waters launched a food revolution, but they're wrong. That was only an ingredients shift. It didn't change the culture surrounding food."

Restaurants shouldn't just be places for people to order, eat, pay and leave, Hebberoy insists; they should offer a "layered experience" like the kind he says enlivened public eating long ago, back when Alexander Pope and Jonathan Swift holed up for hours in London pubs, gnawing on both grand theories and victuals. To that end, he recently hired a writer-in-residence, novelist Matthew Stadler, who pens brief, bemused essays (considering, for instance, the history of gin) that are placed on the restaurants' tables. Stadler also runs a monthly dinner salon at Family Supper, the Back Room, for which speakers—writers and artists—create original monographs that are letterpress-printed and circulated to their fellow diners.

"I have cookbook offers coming out of my ears," Hebberoy says. "I have five people asking me to open a new restaurant every week. But I don't want that." Instead, he's shopping a proposal for a book called Kill the Restaurant. The book would celebrate America's illegal supper clubs in a series of essays aimed at dismantling dining conventions—for instance, the idea that a restaurant needs to be in a pleasant, walkable neighborhood. Hebberoy likens Kill the Restaurant to Rainer Maria Rilke's Letters to a Young Poet. He hopes it will inspire "18-year-old kids to cook for their punk rock friends and charge them for it. It could be a major catalyst for change in the world of food." He also hopes to convince Oregon's governor, Ted Kulongoski, to help legalize underground restaurants—say, by allowing diners to sign liability waivers.

Hebberoy sees himself as an artist. Last fall, as part of Portland's Time-Based Art Festival, he worked with chef Troy MacLarty of Family Supper to create a temporary restaurant that served sumptuous meals on tables fashioned out of plywood and sawhorses in a defunct warehouse, which only weeks before was filled with scrap metal and trash.

Revolutionary, artist, whatever Hebberoy calls himself, he's also a businessman who knows how to make a profit. "My restaurants are full every night," Hebberoy says. Still, he notes with patrician poise, "I'm not interested in having the career arc of a restaurateur. I'm more defined by departures."

Gotham Bldg Tavern and Family Supper, 2240 N. Interstate Ave.; Clarklewis, 1001 S.E. Water Ave.; reservations for all restaurants, 503-235-2294.

Bill Donahue, a writer in Portland, Oregon, is a contributing editor for Outside.