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Come for a Brandy Old-Fashioned, Stay for Winslow Wise

At The Caribou Tavern, the longtime bartender does double duty slinging Wisconsin classics and running the legendary griddle.

The Caribou Tavern, or “The ’Bou” as it’s better known, is as old-school Wisconsin as they come. Its glass block windows prohibit peering in from the sidewalk, but its neon sign beckons newcomers and regulars alike to come inside. There, a long wooden bar runs the length of the space, stained glass lights hang overhead, and a griddle at the end of the bar offers snacks like a grilled summer sausage for $5.25, fried cheese curds for $6 or the iconic ’Bou burger for $6.50. In its 57-year existence, more has stayed the same than has changed.

The bar has been a Madison staple since 1966 (its founding owner moved the Dutch Tavern from its location a block away and rechristened it The Caribou Tavern), drawing a crowd that doubles as a cross section of the city’s population: university students, off-duty service industry workers, staffers from the state capitol and out-of-towners. It changed hands in 1970, when the Schmelzkopf family bought it. Dennis Schmelzkopf, a retired police officer, ran the bar until he passed away in 2000; now his son, Dewey, owns it. 

There’s no chef, so the person grilling your burger is the same person stirring brandy Old-Fashioneds, pouring Wisconsin beers on draft or cracking open the cold, cheap beer of your choice. Among those staffing the bar is Winslow Wise, who has been at the ’Bou for 23 years. Wise grew up in Chippewa Falls, Wisconsin, before moving to Madison in 1995 to attend the university. After a short stint at another bar in town, he settled into The Caribou, where he’s become a local favorite as much for his upbeat personality as his distinctive mustache. Punch caught up with Wise to talk about what makes a good bartender, how the neighborhood around the bar has changed and his strategy for cooking all those ’Bou burgers.

How did you get started bartending?
One of my roommate’s girlfriends was a server at the Village Green. Being a poor student, I needed money, and she said that the bar was in need of a bartender and asked if I would be interested. My dad tended bar when he was in school and I look up to my father, so I thought emulating somebody I think is a good person would be a good idea. And so I went in and they hired me.

How did you make the move from there to The Caribou?
I lived half a block from The Caribou, so I would do my studying there during the day sometimes, and after I got done tending bar at the Village Green, I would stop in often for a drink. One night, I was in on a Saturday around midnight and the Saturday night bartender, who would later turn into my brother-in-law, asked me what I was doing at 6 o’clock on Sunday. I said I did not have any plans, and he asked if I would like a job, because the Sunday night bartender had said he was not ever going to come back. I said, “I spend enough time here, I may as well get paid for it.” And I have been here roughly 48 Sundays a year since.

What do you like about bartending?
For about 10 years after school, I had a job doing electronics work for insurance companies, but it was a 9-to-5 that I hated going to every day, so when the opportunity came up to get out of that and tend bar full-time, I jumped at it. I’m happy to be able to go to work. I have a wonderful family that I’ve worked for the whole time that I’ve been here; they take very good care of me. I have really, really good customers. Even with the alcohol that’s involved, it is very rare that there’s an unpleasant experience when I’m working. And I don’t have to take anything home with me. I get to be up at night, which is the way I’m put together. So it is a low-stress, enjoyable job. It’s not really what I was planning on, but it was the slipper that fit.

What qualities make a good bartender?
I like to think that I’m very friendly. I am not as quick as I used to be, but I am always very prompt. People want to be taken care of and have either just worked a hard job or studied hard. I am always watching where everybody is at, either with the food that I’ve made for them or the drinks that they’re working on. When I see that they are almost finished with their drink and I presume that they’re ready for another, I will be moving over there just as they are finishing. Somebody will say, “Could I have another Pabst Blue Ribbon?” and I’ll have surreptitiously snagged a Pabst out of the cooler as I was wandering over there to them, and poof! One will materialize immediately in front of them. Quick service is something that I appreciate as a bartender and I think that the clientele appreciates.

What makes The Caribou a Madison institution?
Its longevity and its location. There is still the laundromat next door and at least a dozen people from the laundromat come in every day. In the afternoon, they have a beer or a soda pop and some lunch while they do their laundry. In the evening, they’ll have a drink and maybe a few shots to make the folding go down a little more easily. This is just a little cinder block place that’s really incongruous with what’s going on in the neighborhood. Madison and Dane County are very popular places for people to move and are growing quickly. But The Caribou Tavern has stayed. The owner, Dewey, is continually getting offers from developers and keeps rebuffing them because this is the place that his dad started and he wants to continue what his dad did. There are 100-year-old houses that are getting torn down and condos are going up everywhere. And still, in the shadow of the Capitol, there is The Caribou Tavern. There’s even the longevity of the people working here. The Schmelzkopf family has been here 53 years. I can count on my hands the number of co-workers I’ve had since I started. There’s Suzy, Wendy, Erin, Kevin, Owen, another Kevin, Jenny, and two Tammys. The two Tammys retired over the pandemic when we were closed for about a year. They were both here for about 23 years. Ruth, who works Thursday and Fridays, has been here 40 years. There is a lot that hasn’t changed, and I think that is comforting for people.

You’re a brandy guy. How do you like your Old-Fashioned?
They’re a little too treacly for me. I like things distilled from grapes because I do like things sweet, but there is a limit. I will enjoy a couple every year with dinner at a supper club since that’s obligatory in Wisconsin. But I certainly enjoy making them—and I make a whole bunch of them.

You have to make drinks and man the grill at the same time. What’s your strategy?
It is all about getting everything ordered in my head so that I know I have enough time to be able to take care of everything. Forty percent of the food I’m putting out is burgers, and since I have made thousands and thousands and thousands of them over the years, I now just instinctively know what temperature everything is at when I’m cooking. So when I’m in the middle of a drink, I can race over and flip something on the griddle then get back and finish whatever round of drinks I’m doing.

The ’Bou Burger is an iconic Madison food. What makes it so good?
We have a griddle that has about 15 years of seasoning on it that imparts a very delicious flavor. It was a sad day when the original griddle died and [we] had to get a new one in there and reseason it. We use good quality buns and get our meat fresh from Jenifer Street Market every morning.

What’s your burger order?
I often get a “Make me whatever you would like, Winslow” request and I like to ask what box people play around in when they have a burger to suss it out, because I want people to get whatever they’re in the mood for. But I like just a straight-ahead burger, maybe with some pepper jack, and a whole bunch of really yummy sautéed onions.

What advice would you give a young bartender just entering the profession?
Bartending can be fun, and if you’re having fun it can be infectious, and hopefully, the customers will enjoy themselves too. And most importantly, they will come back, which is key to most bartending jobs. So, if you’re going to be in the hospitality industry, have fun and enjoy yourself. But the fun also comes with many temptations. I’ve seen many lives in the business get chewed up and some sadly end having succumbed to the seductions. So my advice to anyone I care about who is new to bartending would be to pass along my received wisdom: “Just use good judgment.”

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Amy Cavanaugh is the dining editor at Chicago magazine and a freelance writer. A Massachusetts native, she specializes in cocktails, food, wine, and travel in Chicago, the greater Midwest and beyond. Her writing appears regularly in Chicago magazine in addition to publications such as Food & Wine, Conde Nast Traveler, Fodor’s and Plate.