If you happened to patronize Chicago’s The Violet Hour during the summer of 2008 and snagged a menu, you may have a rare collector’s item on your hands. There, under the whiskey section, is a drink featuring bourbon, lemon juice, Amaro Nonino and Campari. It was called The Paper Airplane.
If that spec reminds you of a better-known drink called the Paper Plane, made with Aperol instead of Campari, there’s a reason.
Toby Maloney, who helped open The Violet Hour, asked bartender Sam Ross, with whom he had worked at Milk & Honey in New York, to create an original cocktail for the Chicago bar. Ross came up with a drink he called the Paper Plane, after a song by M.I.A. (The tune’s name is actually “Paper Planes.”) Ross, who is based in New York, relayed his recipe via a “slightly buzzed 3 a.m. voicemail.” When Maloney played the message, he misheard the name as “The Paper Airplane.”
The drink first served at The Violet Hour did contain Campari; that was not a misunderstanding. The Italian aperitivo was original to the drink that Ross conceived as an equal-parts riff on the Last Word, the pre-Prohibition cocktail that was resurrected in the aughts by Seattle bartender Murray Stenson. Ross combined the Campari with lemon juice as the citrus element, bourbon as the spirit and Amaro Nonino, which Ross had recently discovered, as the herbal part of the equation. But two days later, he was having second thoughts.
“I tried it again and the drink wasn’t quite balanced,” remembers Ross. “It was slightly too bitter and the sweetness wasn’t there. I subbed in Aperol and was immediately satisfied with the result.”
Thus was born the bright orange drink that has gone on to conquer the world (and one Canadian city in particular) while inspiring riffs of its own, a T-shirt and even a bar’s name.
The Paper Plane got its initial leg up because it was simultaneously promoted at prominent cocktail bars in two cities. At The Violet Hour, it quickly became a favorite. “People still order it to this day,” says Maloney, “some even with the original Campari.” (For the record, Maloney prefers the original Campari version, which he considers “an Aussie Rules football match made into a cocktail: chaotic, but structured.”) Meanwhile, Ross immediately began serving it at Milk & Honey and Little Branch in New York.
Soon enough, Toronto joined the fan club.
“The majority of cocktail bartenders in Canada definitely caught wind of the Paper Plane around 2009 to 2012,” says Robin Goodfellow, who worked at Czehoski in Toronto when he first mixed up the drink in 2010. Within a few years, it made the leap to restaurants. According to Goodfellow, people who were familiar with the drink by reputation only started ordering it—without even knowing what it contained. “Who wouldn’t want a bourbon Cosmo?” Goodfellow asks, referring to the drink’s pinkish hue.
Ross caught wind of Canada’s affection for the drink in 2014, when he was dating a woman from Toronto. “Whenever bartender’s choices were being ordered,” he recalls, “Paper Planes were coming out.”
That the Paper Plane took flight was predictable. Ross created it with that purpose partly in mind. He wanted to invent a drink that was not only balanced and delicious, but straightforward, too, relying on four ingredients that were readily available, and requiring no special syrups or infusions. In other words, a cocktail that could be whipped up at any spot with a decent backbar or at home. The drink doesn’t even have a garnish. (As for the most obscure of the four ingredients, Amaro Nonino, the Paper Plane helped put it on the map. “Thanks to Sam Ross, now Amaro Nonino is a must-have in any cocktail bar,” says Elisabetta Nonino.)
Just as the Last Word inspired a hundred riffs, the Paper Plane has spawned its share of equal-parts sours, including the Amen Corner by Nick Brown (bourbon, Aperol, Amaro Nonino and mint) and, perhaps most famously, Joaquín Simó’s Naked and Famous (mezcal, yellow Chartreuse, Aperol and lime juice), which has gone on to become a modern classic cocktail in its own right.
Simó was already tinkering with a variation on the Last Word when he first sampled a Paper Plane at Milk & Honey. “Trying the Paper Plane for the first time made me rethink the possible candidates for a maraschino substitute, as I had been stuck in an initial rut of single-flavor liqueurs—Curaçao, gentian, et cetera,” Simó explains. “I turned my attention to more complex liqueurs like Aperol, Campari, Pimm’s, Cynar and Montenegro. The Aperol-yellow Chartreuse marriage was a big hit, and from there, it was just finding the right mezcal.”
Variations are all well and good, but you know your drink has truly hit the big time when a bar is named after it. That happened when partners George Lahlouh, Dan Phan and Johnny Wang opened Paper Plane in San Jose in 2014. Inspiration struck during a bar-concept reconnaissance trip to New York, which included a round of Paper Planes at the Manhattan cocktail bar Raines Law Room.
“We all loved the cocktail,” said Lahlouh, “and the name fit the bill on being obscure, phonetically fun to say and had some hipness to it.” In addition, it was an apt handle for a bar that intended to focus on modern classic cocktails.
Attaboy, the Lower East Side bar that evolved from Milk & Honey, has gone beyond mixing up the drink to bolster the cocktail’s notoriety. In 2019, the bar collaborated with apparel maker ambsn to manufacture a Paper Plane shirt. The result—short-sleeved, pink, with a design made of little cocktails and paper planes—was offered via the Attaboy Instagram account during the early weeks of the pandemic. The stock sold out in a week.
Today, the Paper Plane has reached such a level of popularity that, 13 years after its creation, it has begun to raise the question: Is it now more popular than Ross’ other modern classic cocktail, the Penicillin?
“I still think the Penicillin is more popular, but I’m actually prouder of the Paper Plane because of its simplicity, deliciousness and its uniqueness,” says Ross. “I had never had anything that tasted like that before this drink.”