Ask a Bartender: 5 Contemporary Classic Cocktails Every Bartender Should Master

Bartenders often like to debate which cocktails should be considered classics vs. contemporary classics.

While there were a bunch of cocktails—such as the Cosmopolitan, Espresso Martini, Bramble, and so on—that popped up in the late ‘80s and ‘90s that could be considered contemporary classics, it’s more common that bartenders look to the 2000s and beyond for contemporary classics that still stand as impressive serves in the modern cocktail landscape where the possibilities of ingredients and spirits are endless. In this decade, bars such as: Milk & Honey, Angel’s Share, Pegu Club, PDT, and Death & Co were homes to bartenders who created timeless, delicious cocktails that are often called on by guests on a daily basis, such as: the Oaxaca Old-Fashioned, Trident, Trinidad Sour, and more.

“There have been lots of bartenders since the early ‘90s and before that have put their stamp on modern cocktails like Dale DeGroff, Jacob Briars, Audrey Saunders, Julie Reiner, Dick Bradsell, and Salvatore Calabrese,” Ryan Gavin, bar manager at Gran Tivoli and Peppi’s Cellar, says. As the 2000s came around, that list of bartenders grew significantly, except this next generation had more ingredients at their disposal as cocktail culture came back into vogue. “I think that a contemporary classic cocktail can be defined as a variation of a known classic that makes the imbiber and the bartender forget that it was just made in the last decade,” Marshall Minaya, beverage director at Valerie, says.

“For example, I think that Sam Ross is the master of contemporary classics. With the guidance of Sasha [Petraske], he created the Penicillin, and the Paper Plane—both cocktails that I make for guests on the regular, as well as being two cocktails that guests ask for on the regular.” Other bartenders such as Phil Ward, Joaquín Simó, Giuseppe Gonzalez, Jim Meehan, Michael McIlroy, Don Lee, and so on also put their stake in the ground with their respective classics—marking New York City as the contemporary classic cocktail capital of the country, and arguably the world. With that, while bartenders should have  a vast knowledge of contemporary classics, here are five that you really must-know.

Penicillin

“I believe that for up and coming bartenders, in New York City especially, should all learn how to make a Penicillin properly,” Minaya says. “This cocktail is on so many menus all over the city, and it is because it checks all the boxes: lemon, honey, ginger, and it makes traditionally non-scotch drinkers drink scotch. The Penicillin is also born and raised in this city, and knowing it first and still sold on Eldridge St. makes it that much more of a New York City contemporary classic.”

Ingredients:

• 2 oz. Blended Scotch
• 3/4 oz. lemon juice
• 1/2 oz. honey syrup (2:1 honey: water)
• 1/2 oz. ginger syrup (1:1 ginger juice: water)
• Islay Scotch float

Preparations: Combine the blended Scotch with the honey-ginger syrup and lemon juice in a cocktail shaker three-quarters filled with ice. Shake until chilled. Strain into a rocks glass filled with one large cube. Layer with the Islay Scotch and garnish with candied ginger.

---

Naked & Famous

“[A] great contemporary classic to keep in your back pocket is the Naked & Famous from Joaquin Simó. At Death & Co,” Minaya says. “This cocktail is a variation of the Last Word, and a Paper Plane. I’m also not sure what it is about a four-ingredient, all equal-parts-cocktail that gets bartenders going and excited, but this trend is definitely real. Mezcal, Aperol, Yellow Chartreuse, and fresh lime juice all equal parts makes for a very balanced and delicious cocktail for those that are more for the agave/smokey shaken cocktail.”

Ingredients:

• 3/4 oz. mezcal, preferably Del Maguey Chichicapa
• 3/4 oz. yellow Chartreuse
• 3/4 oz. Aperol
• 3/4 oz. lime juice

Preparation: Add ingredients to the shaker and shake with ice until chilled and diluted. Strain into a Nick & Nora, or coupe, glass and serve.

---

Oaxaca Old-Fashioned

“The Oaxaca Old-Fashioned is a [contemporary] classic because now people know of mezcal and the balance of sweet to smoky makes it a perfectly complex cocktail that many different people can enjoy,” says Jay Merinque, bar manager at Prospect at Scribner’s Lodge.

Ingredients:

• 1 1/2 oz. El Tesoro reposado tequila
• 1/2 oz. Del Maguey San Luis Del Rio mezcal
• 2 dashes Angostura bitters
• 1 barspoon agave nectar

Preparation: Combine all the ingredients in an Old-Fashioned glass filled with one large ice cube. Stir until chilled, then garnish with a flamed orange twist.

---

Paper Plane

Sam Ross created this bourbon-based Last Word structured cocktail and it has become one of the most popular off-menu whiskey cocktails ordered at bars around the world. “It’s a modern classic for three reasons,” Jan Warren, La Maison and Velier porfolio specialist, says. “It takes a classic, widely known drink recipe, the last word, and turns it on its head; it is made from readily available ingredients that are either bottled or easily sourced and juiced, and it’s goddamn delicious.”

Ingredients:

• 3/4 oz. bourbon
• 3/4 oz. Nonino Quintessentia amaro
• 3/4 oz. Aperol
• 3/4 oz lemon juice

Preparation: Add all ingredients in a shaker with ice. Shake until chilled, then strain into a coupe and garnish with a mini paper plane (optional).

---

Red Hook

Imbibers love a good riff on the Manhattan, and the Red Hook (named after the neighborhood in Brooklyn) fits the bill. “A distant cousin to the Manhattan made with rye whiskey, Punt e Mes, and maraschino liqueur,” Gavin says. “This [cocktail] was created by Enzo Errico at Milk and Honey NY.”

Ingredients:

• 2 oz. rye whiskey
• 1/2 oz. Punt e Mes
• 1/4 oz. maraschino liqueur

Preparation: Add ingredients to mixing glass, stir until chilled and diluted, then strain into Nick & Nora glass.