When Toby Cecchini invented the Cosmopolitan back in 1988, he didn’t intend for it to make its way to a cocktail list at all, let alone become a decade-long bastion of urban drinking.

“When our regulars first started asking for it, I was weirded out,” says Cecchini, now the owner of Brooklyn’s Long Island Bar. “Pretty soon, I noticed that people were asking for it in other bars around town and it just absolutely blew my mind.”

The inspiration for the drink wasn’t so much flavor as it was color. Cecchini, then in his mid-20s and working at Tribeca’s The Odeon, had set out to create a spin on a pink cocktail that a waitress had reported was making its way around San Francisco’s gay bars: The Cosmopolitan, as it was known, was a mix of rail vodka, Rose’s lime and grenadine.

Swapping out Rose’s in favor of fresh lime juice, which The Odeon was using in their Margaritas, Cecchini built his drink as a simple sour. He incorporated two parts Absolut Citron (a new-to-the-market offering that ignited the flavored vodka craze) with one part each Cointreau, lime and Ocean Spray cranberry juice. Served up and garnished with a lemon twist, it’s a notably paler rendition of the cocktail that most drinkers now associate with the Cosmopolitan.

“The Cosmopolitan almost looks like a White Lady,” says Cecchini of the drink, made in a 2:1:1:1 ratio. “The pink is so delicate—it should be just a blush, really—that when it’s drunk you almost can’t tell it from a Margarita.”

But as the drink made its way across New York’s downtown bar scene, the recipe became subject to the proverbial game of telephone—no one knew the proper specs.

“It was always made wrong, and you could tell, because it looked like a Negroni,” says Cecchini. “Nobody was doing the proper amount of lime juice…There was too much cranberry. And still, to this day, people never get it right.”

Adding to the confusion, in the mid-1990s, one of the city’s most famous bartenders gave the Cosmopolitan a personal spin. Dale DeGroff, whom New York magazine credited as the inventor of the drink after he put it on the menu at the Rainbow Room in 1996 (he was quick to reject that claim), garnished it with a flamed orange peel. In addition, his recipe—which graces the cover of his The Craft of the Cocktail, published in 2002—dials back on both the Cointreau and the lime juice and ups the ratio of cranberry to vodka. By the time Sex and the City turned the drink into a nationwide sensation, having first appeared in the second season, it had already earned itself a muddy history.

Cecchini admits that he’s partly to blame; not wanting to go down as “that dick who invented the Cosmopolitan” (his words), it wasn’t something he liked to talk about. In the years since, he’s repeatedly referred to the drink as his albatross—something he’s begrudgingly embraced by virtue of its iconic place in the canon. (The Cosmopolitan, it’s worth noting, is among the only craft cocktails to come out of the ‘80s. Two other notable examples, the Espresso Martini and the Bramble, were both the work of London bartender Dick Bradsell.)

Looking back on the drink today, Cecchini notes its two-dimensionality compared to many of the cocktails making the rounds. “It sort of screams ‘80s… [and] I can’t tell you I’m terribly proud of it,” he says. “What it’s become is bonkers.”

Certainly, thirty years later, there are plenty of bars offering their own tongue-in-cheek plays on the infamous drink, updating them with modern flourishes. Take, for example, Dave Fernie’s riff, created at LA’s Honeycut, which swaps the cranberry for housemade pomegranate grenadine, its tartness bolstered by citric and malic acids. Cecchini also cites an example made by Nick Strangeway that included an herbaceous lemon-flavored vodka, part of the short-lived Absolut Craft series, as being particularly complex.

“If you’re playing Mister Potato Head and swapping something in and something out…that’s sort of charming,” he admits, before brainstorming, in passing, an idea to build the Cosmopolitan using Blanche Armagnac. Still though, Cecchini offers a reminder that the drink was very much a product of its time.

Whereas bartenders have always been prone to riffing on the classics, updating them to reflect the flavor of the moment, there’s also something to be said for taking these drinks at face value. The Cosmopolitan might occupy a nebulous space in time, having arrived just before the onset of “craft,” but looking back, it’s still among the only cocktails from the period that will surely go on to join the modern lexicon, and, surely, there’s plenty to be said for that.

“You have to understand where this was in time: This was when everybody was just drinking Martinis and Gin and Tonics and whatnot,” he says. “Bear that in mind… What it is, qua a cocktail, is a very simple thing.”

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