The Convoluted History of the Southside
Illustration by Adam Waito.


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The Convoluted History of the Southside

The Southside is a cocktail classic, but even some of the most legendary living bartenders can't agree on how it's made or served.

Whether you like it or not, the Southside is the mascot of the craft cocktail movement. Sure, you won't sound like your mom if you order a martini, Manhattan, or daiquiri instead, and you could argue that they're better drinks. Those stalwarts survived Prohibition (with varying degrees of corruption) to become household names. In contrast, the Southside drifted into obscurity like so many other once-loved classics, only to be resurrected by the first wave of intrepid bartenders of the cocktail renaissance—before arm garters turned into a punchline.


The Southside can be made by any bar with gin, citrus, sugar, and mint.

There were other miraculous resurrections. The Bizzy Izzy Highball remains one of my favorite classic cocktails of all time, but it's the kind of order that makes you feel like a dick at even the most studious cocktail bar. Cold-calling an Aviation is a fine order at most cocktail-friendly bars today, but there was a time when only those clued in knew that meant crème de violette, and not everybody had access to it.

The Southside, on the other hand, can be made by any bar with gin, citrus, sugar and mint. Stocking its most challenging ingredient, mint, is really just a way of saying, "Yeah, OK, we kind of give a shit." And when we order a Southside, that's really all we're asking for.

Today, the Southside is ubiquitous. From the cocktail churches to the corner joints, this drink can be and has been made, included on menus, and taken for granted. Its the sort of drink nobody thinks about often, despite some of us craft bartender types making it a dozen times on a healthy Saturday night. Of course, as anyone on social media with a lot of bartender buddies knows, not putting much thought into something doesn't necessarily stop us from having strong opinions on it.

Being a little controversial never hurt a cocktail. The Manhattan and the martini both have their own naming mysteries (and accompanying legends and lies), but the Southside's almost seems like a deliberate troll. Sure, Chicago has a Southside. So does Long Island. You know what? Everywhere has a Southside. I bet it's named for all of them.


That's not the confusing part. A little storytelling—or even a lot—is fine. It takes a fair amount of bullshit to damage a bartender's reputation. Putting the wrong things in a glass are much more likely to get a guy or girl into trouble with the cocktail mafia. There are other drinks that come part and parcel with heated debate. Another favorite classic of mine, the Jack Rose, is varyingly served with lime or lemon from bar to bar, but the argument over that drink never seems to reach the same pitch as it does in when discussing which citrus belongs in a Southside.

And that's not all. People can't even decide on the presentation of the drink. Is it served, as so often the case today, in the coupe (or a "cocktail glass," as it's sometimes known in the old recipes and we presume is synonymous)? How about on the rocks instead? Fuck it. How about with club soda? Sure.

This is the part where I start calling in favors, reaching out to really famous, super-talented, and downright legendary bartenders to ask them about a drink that I think is totally acceptable. There's an answer, right? There has to be.

"The drink was the house drink at the 21 Club [at] 21 West 52nd street," Dale DeGroff, author of Craft of the Cocktail, tells me. "The drink actually evolved form an older drink called the Major Bailey. The Major Bailey hailed from Jack and Charlie's earlier joint called Puncheon at 42 West 49th Street. There were four locations in all before 52nd street…The Major Bailey recipe was almost the same as the Southside, but it used both lemon and lime juice and it was served short over ice cubes without the soda. Jack and Charlie referred to this drink as 'a mint Julep with gin.'"


Dale points me to "21": Every Day Was New Year's Eve, H. Peter Kriendler's memoir and history of the family of bars that were absolutely essential to New York City at the beginning of the 20th century. It's a great book, filled with colorful historic details, but it's very, very light on recipes. There's been some debate as to what exactly Jack and Charlie's Southside was made of and looked like in its earliest years. While the ingredients for the Major Bailey are missing, I do locate Kriendler's assertion that the Southside was born in-house. As was the Bloody Mary. And the B&B. And, I shit you not, the Ramos Gin Fizz.

How do we get from this nebulous sour with mint, in any old glass, with our without ice and soda, to our tidy little coupe filled with an up gimlet with mint?

The oldest recipe I know of for a cocktail called "Southside" shows up in Hugo Ennslin's Recipes for Mixed Drinks from 1917. This book has the distinction of being the last American cocktail book published before Prohibition and is like a little sliver of New York cocktail DNA frozen in amber. Toward the back of my little reproduction, tucked in the fizz section, is a Southside Fizz. The drink calls for both lemon and lime (because fuck you, that's why), and as with most fizzes of the time, is ostensibly served sort of like a shot with a splash of club soda.

"You're supposed to shoot it down," David Wondrich, author of Imbibe and probably greatest living authority on cocktail history, tells me. "This was before Alka-Seltzer. It was medicinal."


It takes David about ten minutes to track down an older version of the Southside than the one in Ennslin's book. Pulling a clip from an old Life magazine ("But a different Life, not the one you know") he finds a recipe for a Gordon's South Side, circa 1913. This one calls for just lemon juice, but adds more confusion: It's a frappé (a mixed drink served on crushed ice) and is even pictured in the magazine in a tall, frosty julep tin, with ice shards poking out of the top.

"Anyone who hooks his cart to any cocktail history is going to go off road," David warns me, before giving me a brief rundown on what he knows about the drink. The story about it being named after the Southside Hunt Club is as good as any, and it fits into the turn-of-the-century timeframe. If that story is true, all we have is guesses as to what went in the glass … and what the glass looked like.

Ordering a Southside in a cocktail bar in 2016 will get you an almost identical drink, nine times out of ten (with the tenth bartender getting super-pissy about everyone else's Southside). How do we get from this nebulous sour with mint, in any old glass, with our without ice and soda, to our tidy little coupe filled with what bar legend Toby Maloney describes to me as "an up gimlet with mint"?

Thus begins my game of cocktail telephone. I call every bartender I can think of who might know: "When was your first Southside? What was in it? Who served it?"


In 1999 and 2000, Sasha Petraske would have made you a Southside whether you wanted one or not.

This list is embarrassingly long, and I cashed in more favors for five minutes then I rightly deserve. At one point, somebody points out that I'm on a fool's errand.


"There were not many cocktails served at Milk & Honey in the beginning," Toby tells me. "Martinis, Manhattans, daiquiris, and gimlets … not with cordial but fresh lime. Adding mint to a sort-of gin daiquiri was a short step. It was called a Southside cause Sasha [Petraske] must have come across it in a book somewhere. He never revealed any history to me at all."

David echoes this sentiment: "In 1999 and 2000, Sasha would have made you a Southside whether you wanted one or not."(If you have, for some reason, read this this far and don't know who Sasha was, don't waste your time. Stop what you are doing and go find out.)

"By the time I got to Milk and Honey, the Southside was a mint gimlet, served up. It was not double-strained, because there were no double strainers back then," Toby affirms. "If that drink had been introduced to me with crushed ice, I would think it would have gone lemon, like a gin fix. I think it was just the style of glass that Sasha went lime. It makes sense in my head; that that's how it would have made sense in his."

Cocktails, like a lot of passions, aren't always remembered correctly if you're doing them right. Even Dave-fucking-Wondrich can't quite remember if Sasha always served his Southsides up, suggesting that the odd tall Southside maybe came across that bar to him a few times. Imagine the gauntlet of tastings at Milk and Honey in 1999 before Sasha and company decided what his house Southside was going to be. Or those same tastings at the 21 Club (where what went in a South Side over the century is still contested). Maybe Sasha had his version there first, or at some other bar entirely. Maybe we should have focused more on George E. Lee Sr., another Southside advocate who passed away recently.

It might be a fool's errand, but I learned something I didn't know before giving it a go. It doesn't really matter who made the first "gin daiquiri with mint." The person who made it for you probably had it made for them by someone who had it made at Milk and Honey.

The Southside is the mascot of the craft cocktail movement because it's the product of a bunch of stalwart bartenders—all of them authors. And like so very much of what we all do, a lot of us do what we do the way we do because of Sasha Petraske.