The cops couldn’t get rid of the speakeasies, and, as it turns out, legalization couldn’t either. We just can’t help ourselves. The cocktail industry, and indeed the cocktail drinking public, have been reliving the 1920s through the era’s “secret” bars for almost two dozen years. There’s something quietly exciting about them: the hidden entrances, the dim lights, the renewed focus on quality ingredients and excellent cocktails.
They feel like a passageway to the past. But for all the twisty mustachios and suspenders, there was one thing missing from the Roaring ’20s revival: the roar. Having just put the Great War and the Spanish flu behind them, the whole 1920s world seemed to dress up and hit the town, Prohibition be damned. Now, 100 years later, and after more than a year of being cooped up, we’d love for ebullience to once again be the flavor of the day.
With that in mind, we’re highlighting cocktails that reflect that irrepressible era. Some of these are still front of mind, some have faded from memory, but all evoke a bygone time that seems nonetheless strangely present. All parties this year and next are Roaring ’20s parties, whether explicitly or not. Have a cocktail to match.
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Southside
Image Credit: Chelsie Craig There are conflicting claims about the Southside. It was invented on Long Island, at the South Side Sportsmen’s Club. Or was it invented on the South Side of Chicago during Prohibition, a favorite of Al Capone? Both sides stand their ground, but we know two things for sure: First, in the 1920s it was the house drink at Manhattan’s most popular speakeasy, the 21 Club. The second is that it is almost prototypically delicious so everyone loves it. No wonder they all fight over paternity.
2 oz. gin
0.75 oz. lime juice 0.75 oz. simple syrup 6–8 mint leavesAdd all ingredients to a cocktail shaker with ice and shake for eight to 10 seconds. Strain off the ice into a coupe glass and garnish with a mint leaf.
Modern Twist: Add a few slices of cucumber to the shaker and top it with soda water after you shake it, and you have an Eastside Rickey, perhaps the most viscerally refreshing drink in the entire cocktail canon.
In image: (clockwise from left) Baccarat Massena Coupe ($390 for a pair); Waterford Talon and Circon Coupe ($320 for a mixed set including noth). Ki No Bi Kyoto Dry Gin ($75)
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Stinger
Image Credit: Chelsie Craig At the time this cocktail was invented, a “stinger” meant a quick punch to the head, which fits: Weighing in at a record low of just two ingredients, this little bruiser doesn’t disappoint. The Stinger defies categorization—it’s boozy like an Old Fashioned, which suggests after dinner, but bright with mint, which suggests before. There is no time of day or year you’re “supposed” to drink it, which is ideal, because that means you can have it whenever the fancy strikes.
2 oz. Cognac
1 oz. crème de mentheAdd all ingredients to a cocktail shaker with ice and shake for six to eight seconds. Strain into a rocks glass over crushed ice and garnish with a mint sprig.
Modern Twist: Whether this is a fabulous before-dinner drink or a fabulous after-dinner one depends entirely on the quantity of crème de menthe. After dinner, make it sweet, as printed above. Before dinner, bring the liqueur down to 0.5 oz and enjoy a bracing appetite stimulator with a cooling minty exhale.
In image: Baccarat Faunacrystopolis Tea Tumbler ($530 for a pair)
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Boulevardier
Image Credit: Chelsie Craig Invented in Paris in 1927 by expat American playboy Erskine Gwynne, the Boulevardier is the perfect mixture of European refinement and American impetuousness. In a world full of primo Negroni variations, the Boulevardier remains the best of the lot. Gin’s crystalline sharpness is replaced by the broad shoulders of American whiskey, robust with oak and vanilla, which gives the cocktail force and depth. If drinking a Negroni is like wearing a tailored suit, drinking a Boulevardier is like wearing it with a grin and a big cigar.
1.5 oz. bourbon
1 oz. Campari
1 oz. sweet vermouthAdd ingredients to a rocks glass with as large a piece of ice as you have. Stir until cold, 10 to 20 seconds, and garnish with an orange peel.
Modern Twist: While the original cocktail calls for bourbon, many modern palates have adjusted to spicier rye whiskey, which brings more heat and some much-welcome tension. The higher the rye content, the better.
In image: Baccarat Harmonie Tumbler ($280 for a pair). Balvenie 15 Single Barrel ($110)
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Mamie Taylor
Image Credit: Chelsie Craig What’s that ginger beer cocktail that everyone can’t get enough of? Before the Moscow Mule and the Dark and Stormy, the Mamie Taylor, made with scotch, ruled the day. The cocktail was invented at the turn of the 20th century, named for an opera singer who, after a warm afternoon on the lake, asked for something “long but not strong.” It was hugely popular—ginger beer, as it turns out, is a magic ingredient, as capable of bringing life to vodka as it is taming the eccentricities of scotch, and making either appropriate for any occasion.
1.5 oz. Scotch whisky 0.5 oz. lime juice
4–5 oz. ginger beerAdd ingredients to a tall glass filled with ice, then stir briefly with straw or spoon to combine and chill. Garnish with a lime wedge or a piece of candied ginger.
Modern Twist: Give it the mule treatment with a dash or two of Angostura bitters, to further highlight the spice in the ginger beer.
In image: Ralph Lauren Stirking Highball ($125 for a pair). Colonel E.H. Taylor Straight Rye ($70)
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Mary Pickford Cocktail
Image Credit: Chelsie Craig The Mary Pickford is one of those drinks that looks and tastes exactly how it sounds. During Prohibition, it was invented in Cuba, where drinking was still possible for any and all Americans lucky enough to get there. You don’t even need to know who Mary Pickford was, or that she was one of the most recognizable actresses of the 1910s and ’20s, to appreciate that the Mary Pickford cocktail—beautifully pink in an elegant glass—has been answering the call of “fruity and not too sweet” for nearly a century.
2 oz. white rum
1 oz. pineapple juice 0.25 oz. grenadine 0.25 oz. maraschino liqueurAdd all ingredients to a cocktail shaker with ice and shake for eight to 10 seconds. Strain off the ice into a martini glass or coupe and garnish with a maraschino cherry on a pick.
Modern Twist: The original recipe called for 2/3 pineapple juice, 1/3 rum, ratios that we reversed in our recipe. If you prefer your drinks on the softer side, feel free to move the rum down and pineapple juice up as desired.
In image: Baccarat Massena Coupe ($390 for a pair)
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Aviation
Image Credit: Chelsie Craig Hugo Ensslin, in his 1916 cocktail book Recipes for Mixed Drinks, doesn’t say why he named the Aviation as he did, but it’s not like he had to. This pale sky-blue cocktail, invented during the heady dawn of air travel, was forgotten after Prohibition, only to be picked up and dusted off by the early craft cocktail renaissance bartenders of the 2000s. It’s bright and tart, fruity and floral. It’s a drink to sip while admiring the color of the sky and dreaming of possibilities.
1.75 oz. gin
0.75 oz. lemon juice 0.5 oz. maraschino liqueur
0.25 oz. crème de violetteAdd all ingredients to a cocktail shaker with ice and shake for eight to 10 seconds. Strain off the ice into a martini glass and garnish with a maraschino cherry on a pick.
Modern Twist: Bartending books as early as 1930 omit the crème de violette, as it used to be hard to find. Feel free to make it that way if you like (it’s still totally delicious), but if you do, throw a dash of orange bitters in there—this turns it into the Casino cocktail, a Prohibition-era charmer all its own.
In image: Waterford Lismore Black Martini Glass ($250 for a pair)
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Sidecar
Image Credit: Chelsie Craig Cognac’s intrinsic associations are all about snifters and smoking jackets, but then there’s this juicy little number, likely invented in Paris in 1919. The Sidecar couldn’t be simpler—it’s Cognac enriched by orange liqueur and electrified by lemon juice—and has been delighting fair-weather brandy fans for more than 100 years. The drink’s particular magic comes from the citrus, which spotlights the fact that behind all the oak presence, Cognac is a grape-based spirit, with a rich and fruit-driven core.
2 oz. Cognac
0.75 oz. lemon juice 0.75 oz. CointreauAdd all ingredients to a cocktail shaker with ice and shake for eight to 10 seconds. Strain off the ice into a sugar-rimmed coupe glass and garnish with an orange peel.
Modern Twist: Opinion divides on whether the sugar rim is appropriate: Its function here is to add a little kiss of sweetness to a drink that is, frankly, too tart. If you’d like to omit it—or just to bring a little supplemental balance—add about 0.25 oz. simple syrup to the cocktail before you shake.
In image: Tom Dixon Puck Coupe Glass ($95 for a pair)
