Always Glad You Came

Illustration by Nate Otto

On the day after Christmas, as buckets of freezing rain and sleet fell on the Chicago area, I white-knuckled my way to the 61-year-old Uptown Tavern in the suburb of Westmont to interview the owner, Bill Carlson. I wasn’t expecting to find anyone at the bar, but when I walked in, there were 15 people drinking, chatting and watching TV.

It’s always busy at the Uptown, which hosts fundraisers, serves a free turkey dinner on Thanksgiving and provides a place for local third-shift workers to unwind in the early morning. Not bad for what Bill calls “a little shot and a beer bar.” He knows that even a humble tavern needs to keep evolving to survive. Pop open a can of Old Style and settle in for a story about a friendly neighborhood dive.


WAILIN: Bill Carlson has two rules when it comes to bartending. Number one: Always pay attention when you’re behind the bar. Bill takes this principle so seriously that eight years ago, he stopped smoking months in advance of the state smoking ban so he wouldn’t have to step out for breaks.

BILL: I’m so anal about waiting on customers that I wasn’t going to be outside when a customer might need a beer or a drink. So, you know, I get very upset with my bartenders if they turn their back to the bar to have a conversation. You can have a conversation and still scan the bar to see if somebody needs something.

WAILIN: Bill’s second rule of bartending, which relates to the first one: Listen to your customers.

BILL: You just try to be a good listener and not offer too many solutions. That seems to work out better than just — being a good listener is, I think, very important and remembering what they’re telling you. So if they come back in a day or two, you can ask them about it. Yes, I do believe that’s very big.

WAILIN: Bill has been listening to his customers for a long time. He started bartending in 1977 and has spent most of his career as the owner of the Uptown Tavern, an unassuming watering hole in the Chicago suburb of Westmont that’s been open since 1955. Bill describes the Uptown as just a little shot and a beer tavern, but the bar has been constantly evolving beneath its wood-paneled surface, and that’s largely because of Bill’s listening skills. Not just lending a sympathetic ear at the end of a long day, but paying attention to what his customers want. For example, no one seems to order Cutty Sark or JB Scotch anymore.

BILL: Now you better have Johnnie Walker and Dewar’s and onto the next line of ’em, you know. Bush Mills Bourbon, you know, I’d never heard of it. “You gotta get Bush Mills, everyone likes Bush Mills.” Okay! We got Bush Mills, you know? So just stuff like that. So you gotta keep up with the times, ask your clients or your customers what they like, what’s the new trend, you keep up, you’ve gotta keep up, you know, think young. You want a younger crowd to come in and spend their money as far as the bar business, think young and ask questions, ask your people, ask the customers at night what they want, you know, what they’re looking for.

WAILIN: Pull up a stool at the Uptown Tavern on this episode of The Distance, a show about long-running businesses. I’m Wailin Wong. The Distance is a production of Basecamp. Introducing the new Basecamp Three. Basecamp is everything any team needs to stay on the same page about whatever they’re working on. Tasks, spur of the moment conversations with coworkers, status updates, reports, documents and files all share one home. And now your first basecamp is completely free forever. Sign up at

BILL: It’s a blue collar town, it’s a working man’s town.

WAILIN: The Uptown Tavern is located in downtown Westmont, Illinois, a town that earned the nickname “Whiskey Hill” during Prohibition because the alcohol kept flowing. The bar is across the street from a commuter train station and kitty corner from where the legendary blues musician Muddy Waters used to live. For decades, the Uptown opened at 6 am and drew an early morning crowd of workers coming from overnight shifts at the nearby hospital and manufacturing plants. In 2009, the village of Westmont banned alcohol sales before 9 am, and those regulars disappeared.

BILL: They stopped coming in because they, you know, if they get off of work at 7 and we couldn’t open ‘til 9, they’d go get something to eat or something. They’d go home and start doing a project or doing whatever, found other places that were open earlier, so kind of lost all that trade.

WAILIN: Bill fought to get the time moved earlier, and the town relented. Starting January first of this year, the Uptown got to open at 7 am, and Bill is hopeful that his morning regulars will return in a few months as word gets around. Here’s how a typical day at the Uptown unfolds.

BILL: It’ll be an early morning crowd. It’ll thin out around, you know, after The Price is Right because it’s very — Price is Right is big around here, from 10 to 11, you know, and then it’s the Jeopardy crowd from 3:30 to 4, and you’ve got your after-work crowd. About 6, they start clearing out, and then about 7, 8 o clock, when we have our live entertainment for the evening starts up, it picks up again.

WAILIN: The Uptown is a modest place, located in a building that used to be a taxicab stand. There’s a large U-shaped bar, four tall tables with stools along the side wall, six TVs, five video gaming machines, a machine that sells Lotto tickets, and a digital jukebox that no one is allowed to play during Jeopardy. Aside from a collection of model race cars and some beer posters on the walls, there’s not a lot of decor. It would be easy to look at the Uptown and think this is the way it’s always been. But the place is very different from how it was in 1988, when Bill started working there after 13 years at another bar around the corner.

BILL: Oh boy, it’s totally changed. It had a drop ceiling. It had one TV that was in that corner that was about a 20-inch TV. It had an antenna, like on the roof, to pick up Bear games ’cause back then, they were getting blacked out because they couldn’t sell out all the time, so you’d pick the signal up from Rockford. It was a bunch of older people in here that were very bigoted, lack of a better word, I mean, and they were, and it was horrible. There were a lot of fights and we cleaned the place out.

WAILIN: A few months after Bill started working at the Uptown, the owner of the bar, an older man who had been in the hospital and wanted to retire, offered to sell him his share of the business. Bill had a young family to support and jumped at the chance. A few months after that, the previous owner’s business partner wanted to sell his share, so Bill brought in a friend to buy that stake. That was in 1989. And there was no real passing of the torch. Bill and the old owner closed their deal at 2 in the afternoon, and Bill was behind the bar that evening when his predecessor came in.

BILL: He walked in at five o’clock, took all the money out of the cash register, and walked out. And that was the only advice he gave me was: Don’t leave that cash register open. ‘Cause I was so appalled, I called my lawyer, and he goes, “Don’t worry about it. In a year from now, you’re not even going to think twice about it.” Twenty-six years later, I still think about it! How could he do that? He had a snoot full and he said, “Hey, you know, we closed today so I guess I get today’s receipts too.” So he just came and took all the money out of the cash register. I was standing behind the bar with my mouth ajar. I was like, what did you just…? And he walked out the door. That was the last time I actually saw him.

WAILIN: And with that, Bill was left to run the Uptown. At the time, the bar had just two beers on tap: Miller Lite and Old Style. The place was the kind of friendly neighborhood dive where you could get your paycheck cashed on Fridays instead of going to a currency exchange, and where you could spend two dollars to enter a non-legal, low stakes betting pool. None of that exists anymore, but Bill’s strategy for running his business is the same as it was back then: Give customers a reason to visit. And the Uptown is popular. On the day after Christmas, in the middle of a downpour of freezing rain and sleet at three thirty in the afternoon, there were 15 people at the bar. Bill knew pretty much all of them. And he was expecting even more people in the evening.

BILL: We’re a little shot and a beer bar, but we’ve expanded as far as the liquor we carry, the beer we carry. We’re trying to keep up with the Joneses kind of a thing, but in order to attract people, you give people a reason to come in, my philosophy, and you make it priced accordingly, you know, to draw ’em in and you have different things to bring ’em in. The poker machines, karaoke, live music, whatever it takes.

WAILIN: You can still get Miller Lite and Old Style at the Uptown, but the bar also stocks a rotating selection of 15 craft beers and a wide variety of liquor. Bill has tried a lot of other things to get people in the door over the years. He’s hosted a yearly pig roast, a blues night, and Super Bowl parties where you could fill up a 25-ounce mug of beer for a dollar. His bar was the first one in town to have a CD jukebox. For the last eight years or so, the Uptown has featured live entertainment. Tuesday is open mic night, where you can play an instrument or read poetry. Thursday is karaoke. And bands play on Friday and Saturday nights. Bill stopped working nights when he turned 50, but sometimes you can still find him behind the bar on busy evenings, washing glasses and getting ice.

BILL: At night, it’s definitely gotten younger, especially when I quit working nights, you know, we went younger with a younger girl bartender, which brought in a younger crowd and it just makes sense, I mean, without a doubt. And as I’ve gotten older, you know, I could see like the crowd getting younger and younger and when I come in here at night, from knowing 95 percent of the people, that’s down to, like if I come in here at 10 o clock at night, five percent of the people know who I am. Who’s the old guy over there, you know? Or I’ll go behind the bar and do something, you know, who’s that? They don’t know me. Which is nice, it really is.

WAILN: The daytime crowd tends to be older and more price conscious, and Bill is sensitive to that. He’s kept his prices down, charging just two seventy five for a pint of Miller High Life or Miller Lite, and he offers different specials each day. The Uptown crowd might be price conscious, but it’s also very generous. Bill holds a lot of fundraisers. It started years ago, when he raised money to cover the funeral expenses of a friend who had died without the means to be buried, and the philanthropy grew from there. The Uptown raised over ten thousand dollars for Make A Wish in 2015. For the last four years, Bill’s hosted a summer cookout to raise money for disabled American veterans.

BILL: So I like the fundraising. I enjoy it, you know, I think it’s for a good cause and people get behind it, even people who don’t have a lot, you know, we try to do raffles and stuff like that for people that don’t have a lot of money but they want to give, so it’s not the upscale raise a hundred thousand dollar kind of a deal, but it’s more local, you know, and people get behind it.

WAILIN: Bill estimates he’s raised ten thousand dollars for disabled American veterans over the years. There’s a bucket over by the video gaming machines for unredeemed vouchers. When someone is left with just a few cents and they don’t feel like cashing out such a small amount, they can toss their voucher in the bucket.

BILL: They don’t care about two cents or five cents, and I spend the time to redeem them all and turn it into cash. Hey, if it’s a couple hundred here, a couple hundred dollars there, it means something to a disabled American vet. If it’s a car ride to a doctor, whatever.

WAILIN: Bill likes to take care of people, whether it’s the beneficiaries of his fundraisers or his customers. The Uptown is open 365 days a year. It’s hosted weddings, including the ceremony and reception of a couple that met at the bar. On Thanksgiving, the Uptown serves a free turkey dinner with all the trimmings. And on any day, if you come in while Bill’s behind the bar, you’ll get friendly service and a sympathetic ear from a guy who looks a lot like the actor Sam Elliott.

BILL: I love people. I love tending bar. I feel like I’m on stage when I’m behind the bar. I’m a very shy person when I’m not behind the bar, and the bar seems to bring out the best in me.

WAILIN: At 61, with almost 40 years of bartending experience behind him, Bill has perfected the art of listening and making his customers feel at home. His son, Bill Junior, who goes by Billy, worked briefly as a bartender and remembered how his dad taught him to always be scanning the bar and not talking too long.

BILLY: I went away to college and I got a bartending job and that was my hardest part, was I didn’t want to say like, “Okay, I have to go now, nice story!”

BILL: People talk and you just gotta walk away and go serve and walk back, and they’ll just continue where they left off. They don’t mind. They want to tell you what they want to tell you. They don’t care.

WAILIN: Bill doesn’t drink and he hasn’t for years — Billy has never seen his father drink. Bill has taken to walking six to seven miles a day. He thinks he’ll work for another five years and then look for someone to buy the Uptown. His business partner — the friend who bought a minority stake in the bar 27 years ago — is still involved with the business, taking care of the bookkeeping and ordering, and at some point he’ll want to retire too. Bill thinks they’ll get out together, although he’s not ready to say goodbye entirely.

BILL: Part of the sale would be contingent on me still getting to work here because I really like what I do, and I really think I’m good at it, and my partner tells me, he goes, you’ll know when it’s time to stop. You’ll know. People will tell ya. Why are you such a crab ass? Or for whatever reason, you know. So, I mean, as long as I get good reports, I’m still busy. People come in and they ask me when are you gonna work or when are you working? You know, you know.

WAILIN: The Distance is produced by Shaun Hildner and me, Wailin Wong. Our illustrations are done by Nate Otto. Special thanks to Billy Carlson for introducing me to his father. I’ve started posting transcripts of each episode. If you want to check those out, visit, where you can also sign up for our newsletter. The Distance is a production of Basecamp, the leading app for keeping teams on the same page about whatever they’re working on. Your first Basecamp is completely free forever. Try the brand new Basecamp Three for yourself at