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Bartender Crush: Matt DiMare, Tapster & Crown Liquors



Bartender Crush profiles Chicago bartenders kicking ass and serving their community with passion, creativity and kindness.


The timeless appeal of a tiny, dark bar is as synonymous with classic American culture as the Old Fashioned itself. For decades, frequenting a bar to sip on a smooth cocktail after hours has been romanticized in various films and literature. For Matt DiMare, that allure is just one of the reasons he became a bartender.


An artist at heart, Matt looks to bartending as both a creative outlet and a craft. He currently leads the cocktail and wine program at self-service bar Tapster and bartends at Crown Liquors. We ventured to the latter bar, an Avondale watering hole, speaking to Matt about Sazeracs, aspirations for the Chicago bar scene, and how his non-traditional path led him to a fulfilling career.


Read our conversation with Matt below. (Note: this conversation has been edited for clarity and brevity.)


LSD: How long have you been a bartender?


MD: I bartended in college, and then after college I didn’t bartend right away but got back into it in like 2011 or 2012, so now like 6-8 years off and on.


LSD: What was one of the things that attracted you to being a bartender?


MD: I liked being in bars at the time (laughs). I’ve always liked the lure of bars, like old-timey dive bars that have that “slice of Americana” kind of feel. At the time, a lot of my friends worked in the service industry, and I really hated the job I had, so I decided to rip the bandaid off and get back into bartending. I was tired of doing things I didn’t care about.


I’m also an artist in other respects, where I’m in a band and do freelance film editing and production work, so working in a bar allowed me to have more of an open schedule and focus on other aspects of my life.


Also I’m like, the opposite of a morning person.


LSD: How did you transition from just liking being in bars to the actual mixology side?


MD: It was odd because it was while I was working at a brewery. I was working for Goose Island and one of the bars I would hang out at a lot, one of the main bartenders there taught me a lot about spirits and classic builds for cocktails. I think that really influenced my passion for [cocktails] and it was kind of on my own exploring and reading more about them. While I was working at Goose Island, we served cocktails and they allowed me to rewrite their cocktail menu. Admittedly, I was still pretty fresh but it was a step that got me into doing more of that.


LSD: What are some of your favorite drinks to make?


MD: I really like riffing off the classics and switching it up. There’s a reason these cocktails have been around for centuries. I would say some of my favorites are Sazeracs, a good Manhattan, and I think there’s nothing better than a well made Margarita. It’s a perfect drink. In the winter, I get a hankering for a really dirty martini.


LSD: What’s your favorite aspect of bartending and what gives you the most satisfaction?


MD: I would say two things. One, is that it’s become an alternate creative outlet for me. Working at Tapster and coming up with large format cocktails that work for a draft system is totally unique. Being able to take a cocktail, extrapolate it out into a large format and then, since we don’t have bartenders touching it, making sure every ingredient, like the garnish, is infused into the drink, you build the flavors into the drink itself.


I think the second part is that it’s fun. The most redeeming part of it is I get paid to hang out with my friends. Why wouldn’t someone want to do that?


There’s something sparkling about nighttime that draws artists to it. Being in a bar is just part of that.

LSD: How do you hope to impact the bartending community?


MD: I would hope that my small, tiny, minuscule influence on the bartending community is that it just becomes—and maybe this is just exclusive to Chicago—more inclusive and accepting of everybody.

If you want to bartend, I’d be willing to train anybody. When it comes down to it, it’s drinking alcohol. I love a really fancy crafty artsy cocktail, but a shot and a beer is also awesome. I want those two ideas to blend more together and I think being able to do both of those things and being really open to everybody’s taste is important.


LSD: What’s the most badass thing you’ve done as a bartender?


MD: So one is having the job at Tapster. Since I’ve been there I’ve probably come up with 200-300 different draft cocktails. There’s a lot more math and food science involved than you might think than in a normal drink. There’s things you should and shouldn’t do, things that get spoiled, and things that just don’t translate to a draft system very well.


I think another more direct answer is two years ago on New Years Eve here, I had the terrible idea of doing a $5 Old Fashioned special. The reason why I did that is because a year prior, there were like 5 people in here at midnight. Well we had a line out the door, you couldn’t even walk through this place. My hands were raw from peeling oranges. We had to have made a thousand Old-Fashioneds that night.


But I’d rather be way in the weeds just holding on for dear life than being bored out of mind. There’s something about embracing the chaos that’s fun.


LSD: Any horror stories or disastrous things that have happened?


MD: My first day on the job [at Tapster] I had an entire shelf of liquor collapse on me. I got hired and the next day I was gonna organize and take inventory and I started stacking all these bottles on the shelves and it literally collapsed. We probably broke 6 cases of booze. An entire case of Campari fell on me, and I was covered in it, bright red and sticky. That was a good way to start a job.


LSD: If you could have drink with a famous person dead or alive, who would it be?


MD: Chris Farley would be fun to drink with—nothing fancy, just, let’s play a game over a bottle of whiskey. The laughs wouldn’t stop.


Watch Matt make one of his go-to drinks, a Sazerac, below.