Behind the Bar with Benjamin Schiller

It’s no secret that I’m a fan of the Weston, the coffee and tobacco infused whiskey cocktail that has become the signature cocktail across Fifty/50 Group bars and restaurants.  Thus, I was excited that Benjamin Schiller, the creator of that cocktail, agreed to sit down with me for an interview.  I met him in Lincoln Square at The Sixth, a cozy mid-century cocktail bar and one of the establishments for which Schiller serves as beverage director.  The interview kicked off with a tasting of his hand-picked Wild Turkey Kentucky Spirit and covered a variety of topics, from shoemaking to what happened when he tried to make a cocktail that encapsulated his day off.


Tasting a hand selected Kentucky Spirit with Benjamin Schiller.
Tasting a hand selected Kentucky Spirit with Benjamin Schiller.


Chicago Bourbon:  What’s your background?  What led you here?

Benjamin Schiller:  “As a young man, I was always impressed with that stereotypical movie scene where the hero of the story looks at a bottle of wine and knows everything about it – even though it’s in a different language.”  At one of his early jobs in the food and beverage industry, many of his bosses had just come from Charlie Trotter’s, and since he “had no bad habits to break,” he learned from all of them, taking in everything like a sponge.  He later ended up at Boka Restaurant group, where his responsibilities included bartending at GT Fish & Oyster and opening Girl & the Goat.  He came over to Fifty/50 about three and half years ago to help open the Berkshire Room.  Since then, he has also been involved with opening The Sixth and most recently Steadfast.


To read Chicago Bourbon’s recap of Steadfast, click here.


CB:  What are your main responsibilities?

BS:  “Product, staff, environment are the main things.  […] I try to stay away from kitsch.  I try to think of an environment that is going to be relevant 2 years, 5 years, 10 years down the road.”  His other aim is to try to make sure the environment remains approachable for guests, not just trying to serve fellow bartenders and mixologists.


CB:  What does it take for you to bring a new spirit into the bar?

BS:  When it comes to picking spirits, Schiller tries to balance his personal preference, what the guest wants, and what provides the most bang for the buck.  He warns of the dangers of leaning too far in any direction.  If he were to rely too heavily on customer preference, his guests would likely miss out on trying new expressions and widening their knowledge.  Swinging too far in the other direction, however, can be intimidating to customers – even beverage directors.  “Sometimes I walk into a bar and I don’t know what […] half the stuff is,” he explained.  “What the hell is my aunt from Crystal Lake, Illinois going to do?!?”  Finally, while he keeps in mind what is trendy, he also sticks to the classics.  He gestures to the bottle of Kentucky Spirit on the table.  “Can I pick out a lot of other products that are 10 years old, 101 proof, no caramel coloring, no additives, that I can sell for 12 dollars?  That’s that good?…I don’t know…”


A bottle of Wild Turkey Kentucky Spirit hand selection by Benjamin Schiller.
A bottle of Wild Turkey Kentucky Spirit hand selection by Benjamin Schiller.


CB:  How many people have kissed you for inventing the Weston? 

BS:  “Ya know, that one I put out there as, well, I don’t want to say a joke, but a little tongue-in-cheek.”  He went on to explain that it came about during a period while he was with Boka group when his phone was ringing off the hook and he barely had a moment to himself.  If he ever did manage a day off, he would go through the same routine.  “I would get some Dark Matter espresso and have, like, 10 of those.”  Then he would head to Whole Foods for grocery shopping.  “You know when you get to the checkout and they have those brutally expensive chocolate bars?  I’m a sucker for those,” he admitted, shaking his head.  Next he would pick up some spicy Panang curry and head home to relax on his porch with a cigar and some whiskey.

He realized that the profiles in coffee, chocolate, curry, whiskey, and cigars are all surprisingly similar.  So, he decided to figure out how to make a cocktail that represents his day off, sort of as a joke.  He figured out how to incorporate the coffee and how to make the syrup for the cocktail.  “I don’t really like garnishes that much,” he explained, “but I like things that smell nice, so [I made] tobacco the aromatic garnish.  Less is more, so what’s the simplest format in the world?  Pretty much the Old Fashioned.”  After combining all the flavors, he gave the drink his middle name, since at the time this was meant to be a bit of a joke.  He simplified the drink a little from its first iteration, and it took off.  Schiller brought the drink with him to Fifty/50. Based on guest feedback, the group has the Weston on the menu at all the bars he’s worked on.


CB:  Now I know why it was so refreshing after a rough day at work.  It’s a day off in a glass!

BS:  [laughs] Exactly.


The last sips of a Weston, the coffee and tobacco infused whiskey drink.
The last sips of a Weston, the coffee and tobacco infused whiskey drink.


CB:  How typical is that of how you go about crafting a cocktail?

BS:  “Everyone is different.  I like to start with a concept or a name or an idea and then be real simple about it.  […]  I want it to be simple and beautiful, and I want it to smell nice.”  He points out that some of the other bartenders use different methods and that he is happy to have variation – he wouldn’t want everyone producing similar cocktails.


“I want it to be simple and beautiful, and I want it to smell nice” —Benjamin Schiller


CB:  Have you ever had a cocktail just totally flop?

BS:  “I had a series that went down in flames!”  [we both laugh] “I tried doing this whole series of Armagnac cocktails.  I was reading this article and I thought of this big, highfalutin reason.  There was this 16th century who said there were forty-some virtues to Armagnac.” Schiller released three cocktails in a row that were a complete failure.  “They would get sent back,” he bemoaned in the same tone I use when I admit to wearing blue eye shadow in seventh grade.  “So, you step back and you say ‘What cocktails are successful and why?’”  Instead of trying to reinvent a drink, he began to think it might be better to start with tweaks to classic formats.

He then told a story to illustrate.  Several years ago, a group of his industry friends would head to the River North bar Sable after work.  Despite a cocktail list with around 100 options, some would insist on a “dealer’s choice” drink from the bartender.  “This would really annoy the bartenders,” he said.  “Now, it takes some time and effort to come up with 100 cocktails, and price them out, and then get the spirits, and do inventory…and they would constantly do that.”  One night, the dealer’s choice cocktail was particularly impressive, and of course the recipient was curious about what it was.  “It’s a daiquiri,” was the deadpan reply.  “It’s three ingredients.  That’s all I did for you.”  This story stuck with Benjamin, and so he generally tried to stick with a twist on a tried and true format for a more classic, timeless appeal.


CB:  When you’re developing a cocktail, how do you know when you have it “just right?”

BS:  “When there is nothing left to remove.”

Seeing that I was a little surprised by such a concise answer, Benjamin continued on to talk about the importance of listening to his customers not only when testing a new recipe, but more generally.  “It’s important to listen to people who are not me:  […]  the woman in her fifties, the first generation immigrant, or the girl who just turned 21.”  In general, he says it’s important not to play to your own audience.  “I just judged this competition last week and I could tell that a lot of those cocktails were meant to impress other bartenders:  people who use the same lingo, keep the same hours, know the same things, go to the same bars.  They’re not thinking of whoever is going to walk through that door.  We have a really diverse clientele, and that’s the way it should be.”


” I could tell that a lot of those cocktails were meant to impress other bartenders:  people who use the same lingo, keep the same hours, know the same things, go to the same bars.  They’re not thinking of whoever is going to walk through that door.”  —Benjamin Schiller


CB:  How have you seen your customer evolved over the years you’ve been in the business?

BS:  “Well, on the spirits side, I’ve seen people go from getting offended that we didn’t carry their […] blueberry flavored vodka, and now we get complaints that we don’t carry the aquavit from a block and a half away.”


Schiller arrived for the interview undercover, sporting a Weller cap.
Schiller arrived for the interview undercover, sporting a Weller cap.


CB:  What trends do you see emerging now, spirit-wise or cocktail-wise?

BS:  [long pause] “I see a lot of oversaturation and I see a lot of people repeating the exact same thing. […] There must have been an ordinance passed in Chicago that a new taco place has to be opened every ten days.”  He has seen several instances of people trying to replicate a very successful establishment but in a different neighborhood, in everything from speakeasies to tiki bars.  Meanwhile, other more original ideas put forth by very dedicated people are being overlooked.

As far as spirits, he doesn’t see a lot of change anytime soon.  “I don’t think whiskey’s going to go anywhere, I don’t think gin is going to go anywhere.  Everyone thought rum was going to be the next big spirit, but for a lot of reasons I don’t think it’s going to enjoy the success that whiskey has.


CB:  I’d actually like to talk more about that.  I hear often that rum is up and coming.

BS:  “I think regulation is very, very good for spirits.”  In his view, regulations in spirits serves the purpose of putting a floor on their quality.  “It’s nice to know that when that label says ‘bourbon,’ it’s bourbon.  It’s not a mixture of neutral grain spirits and caramel coloring.  It’s nice to know that there’s an age statement, and that represents the youngest drop of whiskey.”  Today, such regulations don’t exist in the rum industry, and in his view, pulling together rum producers from all over the globe is no small task.


CB:  When you’re not behind the bar, do you have any hobbies or interests outside of work?

BS:  “I’m fascinated with shoemaking.”


CB:  I would not have guessed that!

BS:  I don’t even have an interesting reason, other than I just find it interesting.”  He was once mesmerized by a video he saw of a craftsman turn a single, large piece of leather into a briefcase using only simple tools.  “I think if I get good enough, my girlfriend is going to want me to make her shoes one day, but I’m not that good yet!”


CB:  Do you have any advice for anyone who wants to get into a similar role?

BS:  “Think for yourself,” he replied without missing a beat.  “Don’t ever drink or buy anything because someone else thinks it’s cool.”



These words of advice seem to summarize my impression of the beverage director.  Despite Schiller’s success you won’t find him showing off to his peers.  Instead, you might find him behind the bar quietly mixing up cocktails.  His focus is clearly on his customers and creating a welcome environment for them.  His simple, timeless style, both in cocktails and décor, have proven to be a recipe for success.  The Berskshire Room, The Sixth, and Steadfast all have a great selection of whiskeys for either neat pours or cocktails.  The menus are broad enough, however, to please non-whiskey drinkers as well.  I certainly recommend checking them out, especially if you need a Weston after a rough day at work.


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