The Ultimate Bourbon Cocktail You've Never Heard Of

By Kara Newman |

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The Paper Plane—a straightforward box-step of a recipe made with precisely equal proportion of four ingredients—may be the best bourbon cocktail that you’re not drinking. You should be.

Though it’s easy to put together and it’s plenty easy-drinking, it offers a complex flavor profile: still bright and fresh, but with enough heft to make it autumn-appropriate.

Bonus: If you’re not quite ready for a full-on bourbon bomb of a drink (like an Old Fashioned or a bourbon-based Manhattan), this drink involves only a moderate amount of whiskey.

How The Paper Plane Started Flying

There’s some confusion about the drink’s origins, being that it involves a now dearly-departed drinking institution. Was it created at New York’s Milk & Honey or Chicago’s Violet Hour? Sam Ross, now partner for New York’s Attaboy, explains: It was a drink he created for the Violet Hour in 2008, at the request of then-proprietor Toby Maloney.

“He wanted me to riff on a summer drink,” Ross recalls. “Usually drink creation is pretty organic for me, I’m inspired by something or riff on something. This time I sat down and thought of some combinations and worked on it. It’s a riff on a Last Word cocktail,” a classic drink also made with equal parts. Further confusing the issue, the Paper Plane was also made at Milk & Honey, then Ross’s home base, “but we never had any menus,” so the first recorded instance of the Paper Plane would be on the Violet Hour’s summer 2008 drink menu.

Another common point of contention: Is the Paper Plane made with Campari or Aperol?

“The original was Campari rather than Aperol,” Ross admits, and it likely first appeared on the Violet Hour menu as such. But it was later revised to Aperol, and that’s now officially the right ingredient for the drink. Bourbon, however, was always a non-negotiable component.

“That .75-ounce of bourbon,” Ross recalls. “To be sure, I tried it with every type of spirit—rye, applejack, brandy—to really make sure that bourbon was the right fit. And it was.”

Meanwhile, the drink was named for a song by M.I.A., “Paper Planes,” then newly-released (“a spectacular track,” Ross enthuses. “I was listening to it all the time when I was creating the drink.”). But the name of the cocktail only houses one lone aircraft: The Paper Plane.

How Best To Make It

Although this drink is almost impossible to screw up, Ross offers a couple of tips for making an Attaboy-worthy Paper Plane. Although he doesn’t have a preferred bourbon for the drink, he does suggest using a slightly higher-proof bourbon—43-percent to 46-percent ABV—to “add a bit of body.”

Another tip: Don’t over-shake the drink. “You don’t want to over-dilute it or make it watery, but you still want it very cold,” he advises. Other than that, “as long as your lemon juice is fresh and all proportions are equal, there’s no secret to making it right.”

The Paper Plane

Contributed by Sam Ross

  • .75 oz Bourbon
  • .75 oz Aperol
  • .75 oz Amaro Nonino
  • .75 oz Fresh lemon juice

Glass: Coupe

Add all ingredients to a shaker and fill with ice. Shake, and strain into a coupe glass.

Kara Newman is at work on a book about equal-parts cocktails, to be published by Chronicle Books in 2016.

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