If you’re the kind of person who loves old cinemas, ballrooms, and sawdust-strewn saloons, visit Portland. Walking in any direction from the center of town, you’ll quickly notice that this is your sort of place. Movie theaters like the Bagdad and the Mission are so perfectly restored, you can almost see the spit-curled and fedora-clad patrons emerging from a showing of Citizen Kane. Yet inside, after paying an old-fashioned three dollars for a second-run film, stylish couples dine on gourmet pizza and drink microbrews, which are delivered to them halfway through the first reel. At a pub on Broadway, Blazers fans charge up the sweeping staircase to shoot pool beneath stained-glass windows after a home game. And at the White Eagle Saloon and Hotel, hipsters overcome by tequila at the antique oak back-bar can pass out in a comfortable room upstairs.

Portland’s hot spots are all chic in an unconventional, informal way, and highly profitable. And there’s another common thread: They’re all owned and operated by a single family—the McMenamins.

Although they’re at the helm of some of the most happening outfits in the city, Mike McMenamin and his brother Brian aren’t obvious patron saints of cool. Mike, 54, with a big gray beard, jeans, and sneakers, looks like a with-it dad, maybe. Brian, 48, with his mustache and beefy build, could be mistaken for a police detective. And yet anywhere you go in Portland, fun-seekers from every walk of the city’s life pay daily homage to their empire. Mike and Brian run their tastefully renovated properties with a combination of nostalgic tenderness, love for food, and relentless competence.

The empire started small. In 1973, Mike graduated from Oregon
State University, married his girlfriend Mary Alice, and began working at a sandwich shop. He decided that the satisfactions of having a good rapport with his coworkers and feeding customers well were all he needed for a happy life. After he and his wife toured Europe, where he noticed “pubs were places where families went, not just drinking men,” Mike borrowed money and floundered through three attempts at running restaurants in Portland. A loan and a wine-distribution business followed, and again he went broke. Then, in 1983, Mike and his brother Brian (who had struggled with running a pizza shop) asked their father to finance the Barley Mill, in southeast Portland. At last, through a winning combination of family friendliness and the right location, the business thrived.

More bars followed, and then, in 1985, the McMenamins joined a group of brewers lobbying the state legislature for the right to make and sell beer on the same premises. They won, and the brothers found themselves able to put their love of home-brewing to work.

If this were a business magazine, I’d highlight that part of the story, because home-brewing turns out to be a great move. Cutting out the expense of buying name-brand beer from distributors slashes the cost of doing business. With their profit margin wider than ever, the pair opened more alehouses. And if they’d stopped there, they could have enjoyed a good living at the helm of a half-dozen outfits without ever expanding.

But the McMenamins are a restless sort. They have no formal business training, yet their enthusiasm for sprucing up old buildings is endless, and they have no fear of failure. Seated in the old Mission theater, a longshoreman’s union hall turned Portland movie palace, Mike and Brian cheerfully shrug at the various business-oriented queries I toss their way. What are your growth projections? Shrug. How do you choose your locations? Shrug.

“We just go with our gut instinct,” Brian says.

“It’s about liking the look of a place,” Mike agrees. “And getting a feel for what people enjoy about being there.”

A truck driver passing through suggested that the brothers begin showing movies at their pubs, so they bought a screen, scrounged a projector, and soon patrons were cradling pints in front of the dim flicker of classic films. Inspired, the duo bought the Mission, on Glisan Street, and made it a cinema-and-draft house. (Patrons can now catch first-run films at the Mission on a Sunday and return the next evening for Monday Night Football.) Then, after touring an abandoned farm and home for the aged in nearby Troutdale, the McMenamins decided to gamble on opening a hotel: the Edgefield.

After that, it’s just too complicated to list the chronology of renovations and openings. The brothers now own 52 establishments in Oregon and Washington.

I once spent the night in Scranton, Pennsylvania. The city was at one time a railway hub, but trains no longer pass through, so the grand beaux-arts railway station, a protected landmark, became a Radisson hotel. The majesty of the place—marble pillars and floors, a four-story atrium—clashed tragically with the work of the corporate interior designer assigned to the job. Bland carpeting and plastic reception desks floated in the middle of the space as if at a yard sale.

As with Starbucks, McDonald’s, or any other national chain, the Radisson mandate is to make every outlet look the same, no matter where it is. By contrast, every McMenamins establishment looks like a neighborhood joint that’s been around for generations. The pubs are family-friendly (children are welcome at almost every location until 7 p.m., when adults arrive to tipple and it’s time for bed anyway). And each of the brothers’ five hotels feels like the one-of-a-kind work of some long-dead eccentric.

Despite the distinctive feel of each place, all exhibit a deep respect for the existing structures out of which they were carved.

The company literature proudly mentions the Shanghai tunnels and sprawling brothels that used to occupy their properties, and the McMenamins seek out salvaged architectural details to re-create the historic feel of the interiors when the buildings are too far gone to be restored.

At the same time, Mike and Brian aren’t afraid to make major changes. Their greatest successes have been in transforming one building type into another. At the Edgefield, the erstwhile old-age home and its acres of farmland now form a hotel, theater, pub, brewery, winery, golf course, and art gallery. And in the otherwise residential Northeast neighborhood, the Kennedy School, a former K-8, has been lovingly converted into a hotel, movie theater, and restaurant.

It takes a certain sense of humor to enjoy the Kennedy School. Even as a 30-year-old, I began to panic pulling up outside at midday. It felt like being caught off school grounds during class. It must be a common reaction, because the brothers have preserved — celebrated, even — every last scholastic detail. Guests sleep beneath chalkboards in converted classrooms, and they can choose to drink at either the Honors Bar or the Detention Bar. Enormous black-and-white portraits of former students cover the walls, along with murals depicting children and teachers. Overall, the effect is charming and slightly unsettling. It sticks with you.

Whenever a Portlander describes the Bagdad or the Kennedy School—or any of the McMenamins’ operations—to an out-of-towner, the response is usually something along the lines of “Pizza and beer at the movies? Why isn’t every place that way?” There are a few reasons. The first may have something to do with the eccentric character of the Pacific Northwest. In a land where liberal politics and a predilection for the offbeat are all points of pride (“Keep Portland Weird,” reads one bumper sticker), people readily embrace the McMenamins’ carnival aesthetic. Despite enormous, somewhat creepy murals of elderly men riding wheelchairs through the sky, shared dormitory-style bathrooms, and the vague asylum feel at the Edgefield, families overrun the place every weekend. (“I’m terribly sorry, sir,” the receptionist politely tells a caller as I wait to check in, “but all the haunted rooms are taken.”) Another reason is the cost of local real estate. Beautiful, empty buildings in Portland and the surrounding area go begging, and the brothers have developed an eye for a bargain. And as their enterprises grow larger, their patience grows with it: The Edgefield lost money steadily for 15 years and is just now beginning to show a profit. (The Kennedy School, weirder and more luxurious, was an immediate hit.)

The McMenamins were also lucky enough to be just ahead of a trend. “In the ’80s, it saved us money to go on midnight runs to abandoned homes and raid them for old fixtures and old wood,” Mike says. His brother adds, “Now that the antique look is all the rage, it costs a fortune.”

But in the end, what makes McMenamins, Inc., uniquely successful is the brothers’ ability to spot a winning property in a charming neighborhood in their part of the world, and to open the right business there. These guys love old buildings, but they’re not overly sentimental, and they’re not foolish. Although they claim ignorance of any formal real estate wisdom, the pair have a few rules they’ve learned to obey. “You can mix movies with bars, and bars with live music, but you can’t mix movies and live music,” Mike says. They receive several emails a day from admirers all over the country, suggesting classic, vacant buildings ready for the McMenamin touch. I point out hopefully that my hometown of San Francisco has plenty of gorgeous old movie theaters we’d all love to drink beer in, and Mike nods. “Sure, we looked at a lot of places down there,” he says. “But the parking’s a problem, and we just haven’t found the right combination of factors in one building.”

I get the sense that Mike is dancing around something difficult to articulate. Maybe in the same gut-driven way they make all their decisions, the brothers stood in the brisk sunlight of Northern California, sniffed the sea air, watched the BMWs roll by, and just decided it wasn’t their kind of place.

The company has no plans to open anything new for a few years, anyway. The brothers say it’s time to take care of their house for a bit, rather than build another addition. The Old St. Francis, their latest school-to-hotel conversion, opened last year, and they’re developing a line of baked goods and vinegar, which, like their beer, wine, and liquor, are sold only at their restaurants. It’s not that Mike and Brian are afraid of growing too big. They long ago got over any fear of becoming a chain. With 52 locations, let’s face it: They are a chain. But in this corner of the increasingly bland American landscape, the McMenamins are changing what that means.