When it comes to renowned Logan Square bar Scofflaw, gin is the headliner, but not the only draw. Since opening over a decade ago, this cocktail stalwart has fine-tuned its snazzy-but-not stuffy atmosphere and refined-yet-playful rotating menu, and continues to serve warm cookies on the house each night at midnight. The bar is a beautiful place to visit, and particularly cozy in the colder months, with hardwood floors, exposed brick walls, dim lighting, two fireplaces, and a scatter of arrow-backed antique chairs.
Danny Shapiro and his partners Andy Gould, Kristofer Nagy, and Mandy Tandy opened Scofflaw in 2012, and it was well received from the get-go — especially at a time when there was a dearth of gin-focused bars in Chicago. Shapiro met two of his now-partners at a spirits education class and quickly connected over their shared proclivity toward gin. “I think that gin [naturally] lends itself to cocktails,” he says. “It’s the most versatile spirit, and I would drink it in a cocktail 95% of the time. With other spirits, it’s a toss-up as to whether I would have it neat or on the rocks.” Opening a gin-centric cocktail bar seemed like a natural next step.
Scofflaw’s customers share one thing in common: a willingness to try new flavors.
In addition to a healthy gin list which includes their own, Scofflaw Old Tom Gin — a smooth and bright floral spirit produced by North Shore Distillery — there are plenty of gin-less options. And, although they serve a few uncommon spirits and unusual flavor combinations, the menu is approachable and contains a full glossary to make sure no customer is left bewildered.
Today, Shapiro and his partners have grown their business, adding several other establishments through their restaurant group, Scofflaw Group. But their pioneering bar remains a beloved staple of the Chicago bar scene. And they continue to keep it interesting: several times each year, the cocktail menu, now on its 42nd iteration, changes with thoughtful new creations. Here, Shapiro sits down with us to walk through six of his favorites.
“The most popular drink on the current cocktail menu is called Past Life, created by Becca Peterson, one of our bartenders. This drink is a combination of Letherbee Gin, which is made by a local distillery that’s always been a big supporter of Scofflaw; Salers, an aperitif with gentian which gives it its bitterness and special quality; and mezcal, grapefruit, and lemon. It’s served in a rocks glass and given a grapefruit swath. It’s a pretty refreshing, floral, botanical drink. And it’s cool in that it’s a split-base drink, which we’re big fans of here. We’re using gin and mezcal together, which is not super common, although nowadays split-base drinks are becoming more popular.
This drink’s popularity goes to show how hot the agave category is now, and mezcal especially. That being said, it’s not surprising that a gin drink is the most popular option at a gin bar — although that wasn’t always true. When we first opened, whiskey drinks were often as popular as some of the gin drinks. I’d say five years ago, American whiskey was bigger than agave spirits and gin in our locations, and I think now that has changed.”
“A swizzle just means a drink served on crushed ice that is traditionally swizzled (or churned), rather than shaken, stirred, or built. We are on our 41st Swizzle, hence the name. It’s actually the 42nd menu but the first menu didn’t have a swizzle. This particular swizzle is a rye whiskey base, which is relatively uncommon for us because we usually use gin or some kind of clear spirit. It also has Amaro Dell’Etna, pineapple, lemon, and Angostura bitters. It’s tropical and fun, but because of the rye whiskey base, it’s also a perfect cocktail for cooler weather. The Angostura bitters complement the flavors because they have a lot of baking spice, a lot of cinnamon and clove. The amaro in there has some cacao notes and a Tootsie Roll vibe, but the bitterness balances it out. The cocktail is served in a Collins glass and garnished with a pineapple wedge and a little parasol. It’s tropical, bitter, and warm.”
“This drink is by Jimmy Crigler and is basically a riff on a New York Sour. New York Sours are essentially a whiskey sour with a red wine floater on top, which gives a very cool effect. This drink is an aquavit and gin version of that. Aquavit is a Scandinavian spirit, which is why I called the drink Scandi. We’re using Norden aquavit, London dry gin, ginger syrup, and lime, shaking that all up, putting it on rocks in a rocks glass, and then floating red wine on top. So aesthetically, it looks very similar to a New York sour. But flavor-wise, it’s totally different.
Aquavit is a caraway version of gin. If you were to do the drink with 100% aquavit and no gin, it would be pretty aggressive on the palate. And that’s why we changed it to a split base: we stuck with something familiar, and then threw in a little bit of something less familiar. Aquavit has a rye bread/caraway profile to it, which adds a complexity to the cocktail and goes really well with the ginger and gin. Ginger adds that spice and then gin offers juniper and those other tingling botanicals.”
“This one has been a subject of a very minor controversy because of its name. Basically, I’d made this drink before and was really fascinated by the fact that the combination of ingredients yielded something that tastes like coconut but didn’t have any coconut in it. It’s kind of like a grown-up version of a flaming Dr. Pepper or something like that, where you combine these things that aren’t Dr. Pepper, but you drink it and you’re like, whoa, that tastes exactly like Dr. Pepper. This was me accidentally stumbling into something that tasted like coconut, which I’m a big fan of.
So this drink is shaken and served in a coupe, and uses El Dorado 12-year rum, apricot liqueur, lime juice, and Cocchi Americano. Somehow those four things together make something that tastes like coconut.
It’s inspired by one of my favorite cocktails, the 20th Century, which is one and a half ounces of a London dry gin, half an ounce of lemon, half an ounce of Cocchi Americano, and half an ounce of a clear cacao liquor. We took that structure and swapped in an aged rum and swapped in the lime for lemon, kept the Cocchi Americano, and instead of cacao, I used apricot just to try to mess around with a different profile. I was really happy with the result.
The controversy is that we named the cocktail ‘No Coconut’ and wondered if people who don’t like coconut would order it, thinking it doesn’t taste like coconut, and would also potentially scare away those who do like coconut. We’re kind of tricking people on both sides.”
“Originally, this drink was conceived in the late summer as a riff on a Negroni. It’s non-traditional in the fact that there’s no base spirit, by which we mean something that’s 40% ABV — you know, gin, rum, tequila, whiskey, or whatever. The Scapegoat has Amaro Noveis, it has a sherry, and it has Bonal, which is an aperitif with gentian and quinine. The Bonal takes the place of your sweet vermouth, the Amaro Noveis takes the place of Campari, and the Cigarrera Manzanilla sherry acts as the base spirit. It’s served in a chilled coupe, similar to if you were to ask for a Negroni “up” — but it is lower ABV so you can drink a few of them without falling asleep. It’s very light and will give you a comfortable buzz. Again, it’s along the lines of a Negroni but a little bit softer, rounder, and less bitter. Sherry gives it a nuttiness which I think also works in the transition to fall and the cooler weather. It’s prune-y, vegetal, and complex without being too aggressive, like Negronis can sometimes be.”
“Shipwrecker is named for my friend Liz, who is the sister of my co-host, Tim — I host a podcast called Joiners. We were all on a boat recently, and Liz took control of the steering and almost wrecked us. Luckily, no one was hurt and the boat was fine. So there’s the shipwrecker part of it. But Liz always gives me a hard time for never having mixed her a drink in person, face to face. Of course, she’s come into the businesses and had drinks that I’ve created, but she’s never had me personally make her a cocktail. Anyways, that’s her claim. So, I wanted to have a drink on the menu as a nod to her and as a way of saying, maybe I haven’t made you a drink with my own two hands, but this drink is named for you.
It uses her favorite things. We’re using a London dry gin, passion fruit syrup, Cappelletti, which is kind of a bizarro Aperol, and then a little bit of lemon. It’s served in a Collins glass over ice and has a pretty fun garnish, a rosemary sprig through a fresh strawberry, which was my business partner Andy’s idea. Liz had one on the patio and sent me a picture and she enjoyed it. She was flattered to have a drink named after her.”