The British are known for their gins, Ireland has their whiskeys, the West Indies their rums.
Every Alpine country has a bitter digestif, and we’ve got the trinity of France, Spain, and Italy to thank for vermouth.

Melting pot that we are, the US made a name for ourselves bringing it all together. Around the turn of the twentieth century, our shores (with some help from Harry’s New York Bar in Paris during Prohibition) saw the coalescence of these disparate elements into a cocktail culture that’s still booming today. And despite a few years’ dip into Cosmos, Appletinis, amaretto sours, and Jaeger bombs, the old faithfuls are back on top. These days, most bars have a Manhattan on their menu, and it seems like everyone knows their Sidecars from their Sazeracs. But what we don’t talk about much? How to pair these big, boozy flavors with cheese.

For some help in this endeavor, we turned to the guy who literally wrote the book on classic cocktails, Frank Caiafa. Caiafa wrote The Waldorf Astoria Bar Book while working as bar director at the Waldorf Astoria hotel in New York City, Art Deco landmark and one-time haunt of Cole Porter, Grace Kelly, Elizabeth Taylor, and Frank Sinatra (to name just a few). The Waldorf was one of the first hotel bars to offer a free lunch, which according to Caiafa certainly included a variety of cheeses. “They also featured many cobblers, punches, and cocktails, and I’m sure the availability of both inspired plenty of pleasurable pairings,” he says.

In Caiafa’s professional opinion, the best drinks to have with cheese employ some type of fortified wine, i.e., sherry or vermouth. “They bridge the gap between the strength of both the cheese and the base spirit of the cocktails,’ he says. One of his favorite match-ups? “A head-clearing martini and a few savory shards of Parmigiano Reggiano.”

Of course, this topic can’t be introduced without a note on selection—there are dozens of beloved classic cocktails, which means some very cheese friendly faves had to be left out here. The Manhattan is a big one, along with the Aviation, Vesper, Rob Roy, Paloma, Mint Julep, Tom Collins, Corpse Reviver No. 2, and Martinez. Other obvious choices, such as the Martini and Old Fashioned, we jettisoned based on their majority-spirit composition. (Might as well save those for a future article focused on gin or whiskey pairings!) We also omitted milk punches, Mai Tais, the Ramos Gin Fizz, egg white sours, flips, and anything else that leans creamy, as those can often feel like palate overkill beside the richness of cheese.

So, what remains? A lean crew of food-friendly mainstays with bright, herbal, nutty, floral, and refreshing flavors uniquely suited to draw out all the nuance on your cheese plate.

1 ROELLI CHEESE HAUS DUNBARTON BLUE + BOULEVARDIER
Bourbon, Campari, sweet vermouth

This drink, essentially a bourbon Negroni, dates to 1927 and gets its title from a Parisian New Yorker–style magazine published by expat Erskine Gwynne. At once zesty and nutty, it’s perfect for cutting through the fudgy, nut-buttery, and sharp complexity of Dunbarton Blue.

2 MEADOW CREEK DAIRY GRAYSON + SAZERAC
Rye, absinthe, Peychaud’s bitters, sugar cube

Hailing from the Virginia Highlands and New Orleans, respectively, Meadow Creek’s Grayson and the Sazerac cocktail are both a little bit Southern, a little bit French, and a good deal funky. Both are “washed,” so to speak, and together, both can transport you to simpler times.

3 TOMME CRAYEUSE + SIDECAR
Cognac, orange liqueur, lemon

Named for the motorcycle accessory in which one notable WWI captain was driven to his favorite bar, the Sidecar is a glamorous sweet-and-sour libation perfect for washing down the chalky and earthy profile of Savoie-region mainstay Tomme Crayeuse (not to be confused with Maverick).

4 VEIGADARTE CASADO + HEMINGWAY DAIQUIRI
White rum, Luxardo Maraschino, grapefruit, lime

At his favorite bar in Cuba, Papa ordered his namesake cocktail with double rum—not the cheese-friendliest variation. We prefer the traditional preparation, whose lively acidity cuts through the mouth-coating paste of an ash-ripened Spanish goat cheese.

5 18-MONTH MIMOLETTE + THE LAST WORD
Gin, Green Chartreuse, Luxardo Maraschino, lime

Hailing from the Detroit Athletic Club circa 1915, this pre-Prohibition classic is an easy-to- master equal-parts cocktail. Its notes of sweet grass, wild herbs, and citrus liven up the subtle caramel quality and craggy texture of mimolette, making for a very sophisticated combo.

Linni Kral

Linni Kral is a writer, editor, activist, and friend living in Brooklyn, with past lives in Boston, L.A., and Chicago. Her writing has been featured in the Atlantic & Atlas Obscura, among others. She’s happiest in the company of cows, books, and groceries.