If you passed through New York’s iconic Times Square this past June and looked up from your smartphone, you would have seen the world’s largest Paper Plane cocktail.
Seven times an hour for two weeks, a 15-second advertisement for the Italian Amaro Nonino ran on a giant 8,500-square-foot billboard. It showed a bartender making a Paper Plane, which calls for bourbon, Aperol, Amaro Nonino (naturally), and lemon juice.
While this certainly gives you a taste of how well known the drink is, it’s hard to overstate its popularity around the country. It’s gone old-school viral and now appears on the menus of countless bars and restaurants. And that’s not to mention the San Jose, CA, bar, which is named after the cocktail.
No one would blame you for thinking that—like the old-fashioned or Manhattan—the Paper Plane dates back to the 1800s, when the rest of the cocktail classics were invented during the first golden age of bartending. But you’d be dead wrong.
The Paper Plane wasn’t created in the 19th century or even the 20th century. It came into existence just shy of 20 years ago by Australian bartender Sam Ross.
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He learned to bartend in his native Melbourne before moving to New York after the turn of the century and finding his way to Sasha Petraske’s trailblazing Manhattan bars, including Milk & Honey and Little Branch. These establishments played a central role in kicking off the craft cocktail movement.
“A friend told me to check out Milk & Honey, and the second I stepped inside I knew this was where I needed to be,” Ross remembers.
He later bought the bar with fellow bartender Michael McIlroy. The duo still operates the establishment under the Attaboy name. In the spring of 2008, Ross had agreed to create a cocktail for the James Beard Award-winning Chicago bar The Violet Hour.
He started to think about reinventing the Last Word, a classic Detroit cocktail that combines gin, Green Chartreuse, maraschino liqueur, and lime juice. At the time, it was wildly popular with craft bartenders but was largely unknown by consumers.
The Paper Plane came together in the wee hours on a Sunday night. Ross was working at the Lower East Side bar Milk & Honey. Once the crowd cleared, he started trying different combinations of ingredients.
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Coincidentally, a few days before, a regular at the bar dropped off a bottle of Amaro Nonino, which he thought Ross might like to try. Not only did Ross like the amaro but he incorporated it into the recipe he was working on. Ultimately, he settled on a mix of amaro, Elijah Craig 12-Year-Old Bourbon, lemon juice, and Campari. (Later, he switched the Campari out for the softer Aperol.) That summer, Sri Lankan rapper and singer M.I.A.’s song “Paper Planes” was played non-stop in the city, so Ross borrowed the name for his new drink.
Almost immediately Ross knew he created a very special drink, since it combined sweet, sour, and bitter in perfect proportions. “I knew right then and there that I’d done something pretty good,” he says. And sure enough, “it was a hit from day one.” The cocktail ultimately became one of the all-time best-selling drinks on the menu at The Violet Hour. How did it feel for his drink to be proudly displayed over Time Square, the proverbial Crossroads of the World? “Well, if you’d asked little 21-year-old Sammy who just moved to New York from Melbourne if that was going to happen, he would’ve said that’s outrageous,” Ross says with a laugh. “But it was awesome.”
While the Paper Plane is enough to secure Ross a spot in the Bartender Hall of Fame, he created another wildly popular cocktail in 2005: the Penicillin.
Dillon Burke
The drink is very similar to a classic whiskey sour. It calls for blended Scotch, lemon juice, and honey ginger syrup. But the genius lies in a bar spoon of smoky whisky that’s added right before the drink is served. Ross did the impossible: With one recipe, he proved that Scotch can—and should!—be used in cocktails, even the peatiest and smokiest drams.
That was quite a reversal given that many bartenders, distillers, and whisky know-it-alls were in the habit of telling people Scotch could only be enjoyed neat or, if you must, with a few cubes.
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“At the time, there was a stigma that good Scotches should never be mixed with anything and it’s kind of ridiculous,” says Ross. He even admits that when the cocktail recipe was first featured by food magazines online, some of the comments were from readers who were offended by the premise.
The Penicillin has become so popular that many people often mistake it for a vintage cocktail that was discovered in some dusty book. “I’ve certainly had to convince guests in real time that this is my drink and I’m not dead—or 80 years old,” Ross says.
He created the drink one night at Little Branch. A few days before, John Glaser, the founder of boutique Scotch company Compass Box had visited the bar and given the staff a tasting. He and Ross immediately hit it off as long-suffering New York Mets fans. Glaser had encouraged the bartender to make cocktails with his different whiskies. So Ross dutifully mixed up a sour with the Compass Box Asyla Blended Scotch and, instead of using simple syrup, decided to sweeten the drink with Little Branch’s housemade ginger-and-honey syrup.
“It was great,” Ross recalls. “It was a solid whiskey sour riff for sure, but it could be elevated a bit more.” He pulled a giant clear cube of ice from the freezer—which was a real show stopper at the time—and served the drink over that magnificent rock. But the drink still seemed like it needed a final touch.
Ross was impressed by Compass Box’s aptly named, super-smoky Peat Monster. “I just splashed a bar spoon’s worth on top of the rock and purposely served it without a straw,” he says. “I wanted the drinker to bring it up to their nose—get that ferocious smoke and be a little surprised by the mellow, tart, sweet underlying drink.” The cocktail’s ginger, lemon, and honey notes made Ross think of chicken soup with matzo balls, which is often called Jewish penicillin for its supposed healing properties. He simply shortened the name to Penicillin, which gave the drink an old-timey feel.
It took all of 10 minutes to create the drink. “Honestly, I didn’t really think too much of it,” Ross says. “I went to bed that night and it didn’t even cross my mind again.”
Courtesy Dillon Burke
Unlike the Paper Plane, the Penicillin was not an overnight sensation. In fact, when Petraske first tried the drink, he wasn’t particularly impressed, but Ross is quick to point out his boss “didn’t really like smoke” and wasn’t a fan of boozy whisky cocktails. (To be fair, Petraske wasn’t a fan of the Paper Plane, either.)
Slowly, word got out about the Penicillin and—thanks to the dawn of social media—it started to pick up momentum. Fast forward nearly 20 years and now seemingly every bartender in America knows the drink and thousands have been served.
Ross has a theory why it caught on: “The Penicillin is a great entry-level whisky drink,” he says. “But it’s also complicated enough to satisfy the expert drinker as well with the nuances of the smoke and ginger.”
It’s incredible that since the rebirth of the cocktail in the late 1990s, only a handful of drinks, including the Cosmopolitan, espresso martini, and bramble have broken through and become household names.
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Amazingly, Ross’ two drinks are the only modern classics to contain whiskey. And, unlike the Cosmopolitan, he didn’t have help from Carrie Bradshaw and the rest of the cast of Sex and the City.
So, which does he like more? “Just in terms of its cleverness,” Ross says, “I’ve always been more fond of the Paper Plane.”
However, he never tires of making or talking about either of them. He’s still blown away that so many people enjoy the drinks as much as he does.
“If I do nothing else at least those two will be on the tombstone, which I’ll be fine with,” Ross says. “But I still plan on doing some other things between now and then.”
