On the road to Roundup, a new restaurant with a flair


Ed Kemmick/Last Best News

Alex Henderson is the general manager of the original Dirty Oscar’s Annex in Tacoma, Wash., and is temporarily running the show at the new DOA south of Roundup.

Let’s say you live in Billings and you’re in the mood for some substantial food that is also imaginative, even a little edgy. And maybe you’d like to wash it down with some fun cocktails containing ingredients you’d never thought to mix with booze.

Where to go?

How about 30 miles north of Billings on Highway 87, to a roadside tavern on the outskirts of hell-and-gone?

Welcome to Dirty Oscar’s Annex, 16 miles south of Roundup at the base of the Bull Mountains in what used to be the Branding Iron Saloon. The restaurant, modeled after the original Dirty Oscar’s Annex in Tacoma, Wash., opened in mid-August and is already popular with folks in Roundup and workers at Signal Peak Energy’s nearby coal mine.

If it’s good enough for Guy…

As part of my preparation for this story, I watched the “Diners, Drive-Ins & Dives” clip in which host Guy Fieri samples the Tasso Tacos at the original Dirty Oscar’s
Annex in Tacoma.

Fieri and executive chef Aaron Grissom made the tacos look so good that I figured I’d have to order them during my visit to the DOA south of Roundup. Gary Acklin, the head chef there, told me he makes the tacos just as Grissom did for Fieri.

First he cures a fresh pork shoulder for two days, smokes it for four hours, then slowly braises it for six more hours. The spicy, succulent pork is served inside three soft tacos with manchego cheese, green chili crema and pickled apple.


The Tasso tacos.

I’m no food critic, but I venture to say they were the best tacos I’ve ever had. Several diners I reached out to via Facebook felt the same way.

Thinking my meal was adventurous enough, for a cocktail I had the relatively simple Pack Mule—bourbon, ginger beer, lime and bitters.

Next time? Maybe the Elk Sliders (with homemade garlic mayo and provolone), Parmesan Tots and the Buckshot Mojito (see main story for ingredients).

The restaurant’s most popular offering is the Down and Dirty Burger, topped with white cheddar, caramelized leek, homemade garlic mayo and hickory bacon. The more exotic Dead Elvis Burger is popular, too, topped with an egg, candied bacon, peanut butter and mayo.

Two other well-liked dishes are the Parmesan Tots and the Tasso Tacos, both of which were featured on “Diners, Drive-Ins & Dives,” the Food Network show featuring spiky-haired gourmand Guy Fieri.

Cocktails include the Buckshot Mojito, made with Malibu, Silver rum, mint and jalapeno, and the Montana Mary, featuring Original Moonshine, honey cinnamon syrup and lemon juice. The most in-demand drink, General Manager Alex Henderson said, has been the Cowgirl Up, made with Original Moonshine, peach schnapps, cranberry juice and lime.

Stephanie Moncalieri lives west of Roundup and said she and her husband have eaten at the new restaurant at least 15 times already.

“My husband said he single-handedly wants to insure that they stay in business,” she said via Facebook.

Sandy Church, who was there with her husband and a friend one night last week, said the Branding Iron went through five or six owners in the 20 years they’ve lived about five miles up Highway 87.

“We like to give our business to the local people,” she said. “We really hope this one sticks. It’s so refreshing to have something unique.”

The owner of the DOA, as it is called, is Jake Barth, a Tacoma contractor and businessman who also owns some businesses in the Bakken oil fields and was constantly driving back and forth between Washington and North Dakota.

Henderson said Barth was making the drive four years ago and “he kind of stumbled on Roundup and just fell in love with it.”

Barth was already the co-owner of the Dirty Oscar’s Annex in Tacoma, which opened in 2005, and after that first visit he moved to Roundup with his wife and three children. He soon made the acquaintance of Troy Evans, an artist, woodworker, designer and contractor in Roundup.

Evans ended up working for Barth, redesigning the original DOA and then working on another, separate restaurant Barth was developing in Tacoma. Meanwhile, Evans began looking for property in and around Roundup, because Barth wanted to get involved in a business close to his new home.

It was Evans who told Barth that the Branding Iron was for sale. Barth decided to open another DOA in the longtime saloon, a decision that Henderson didn’t understand at first. He was used to Tacoma, where the DOA is located on a busy urban street not far from a college campus, the University of Puget Sound.

But then Henderson came out in May to have a look at the area.

“The second day we were here it all made sense,” he said. In Tacoma, it would be a tough sell to ask someone to drive 15 or 20 miles for a meal, “but out here, everybody’s driving 400 miles a day and it’s nothing,” he said.

Evans did much of the demolition and renovation at the old Branding Iron, which included gutting and completely redesigning the kitchen and building a mahogany back bar. Other changes will be made as time goes on, Evans said, but for now the DOA has a welcome, wide-open feel, with lots of nice woodwork.

During construction, Henderson, who has been with the original DOA since it opened, made multiple trips to Montana with Barth’s executive chef, Aaron Grissom. Grissom, who describes the DOA’s offerings as “New American” cuisine, was featured in the Guy Fieri Food Network segments and later competed on the “Top Chef” television show.

Grissom has been heavily involved in getting the new restaurant going, but he plans to stay in Tacoma, as does Henderson once the new DOA is well established. The head chef at the Montana DOA is Gary Acklin, a native of Seattle who has been in the food business all his life.

He has already found a place in Roundup and looks forward to indulging in his outdoor pastimes, which include target shooting, kayaking and backpacking. He said he learned a lot from Grissom and will bring his style to the new DOA.

“I’d like to think I know how his mind works and what his expectations are,” Acklin said.

If you’re wondering about the name, there’s not much to tell. Henderson said it was the result of “intoxicated logic” when Barth and some associates stayed up drinking one night, brainstorming about a name for Barth’s Tacoma restaurant. The business was located on an alley, which got Barth thinking about Oscar, of “Sesame Street” fame, who lived in a garbage can.


Ed Kemmick/Last Best News

Head chef Gary Acklin and line cook Brandi Berdan, at work in the kitchen of Dirty Oscar’s Annex.

So the concept of Dirty Oscar was born. Barth thought the last word should start with an “A” because he liked the DOA acronym, and after several more leaps of intoxicated logic, Annex was tacked on. It’s a relief for Henderson that there is finally a second DOA.

“Everybody for the last five years said, ‘Oh, annex. Where’s the original one?’ Now I can say, ‘In Washington.’”

Henderson said word of the new DOA has been spreading fast, and locals are getting used to the somewhat exotic fare, which Henderson described as “something you recognize, with a twist.”

The partners decided at the last minute to add pizza to the menu, which turned out to be a good idea. DOA has been doing a lot of takeout business, especially among the miners, and pizza is the most popular takeout dish.

“The whole idea is to do something better for Roundup,” Henderson said, and that doesn’t just mean offering good, fresh food. Building on the kind of relationship they had with restaurants in Tacoma, the new DOA has been looking to partner with other eateries in Roundup, to cross-promote events and to eat at each other’s establishments.


Ed Kemmick/Last Best News

Dirty Oscar’s Annex, 32 miles from the top of Billings Heights, 16 miles south of Roundup on Highway 87.

“If we can dig into the community spirit, that’s going to be something. People will see that,” Henderson said. “That’s not competition. That’s a community.”

Evans has seen that, too. He said he, Barth and Grissom have eaten at the Grand Bar in Roundup on several occasions, and people from the Grand have been eating at the DOA. Barth and his associates have made it clear they want what’s best for Roundup, Evans said.

“It’s really been a nice exchange,” he said. “I really I see our community having a shift in energy because of the interaction. I think Roundup is on a really good track right now.”

Evans said his wife Coila, also an artist, had a writing workshop in her studio recently, and all eight participants, who came up from Billings, ate at the DOA either on the way to Roundup or on the way home. Roundup residents, by necessity, pour a lot of money into the Billings economy, Evans said, so it’s nice to see some money flowing in the other direction.

The new DOA has seven employees and is open from 11 a.m. to 11 p.m. seven days a week. A lot of people have asked when the restaurant plans to start serving breakfast, Henderson said, so that is something the partners are seriously considering.

Becky Criswell, a loan officer at First Security Bank of Roundup, said she has gotten to know the Barths well and considers them, and their restaurant, “a great asset to the community.”

She said she’s eaten at DOA three times and once went there with 13 family members. They tried most of the items on the menu, she said, and “everything was excellent.”

So excellent that her bank has already scheduled its Christmas party at Dirty Oscar’s Annex.

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