Anyone who’s ever attempted to create a cocktail knows the difficulty balancing the characteristics of widely disparate ingredients. The margin of difference between sublime and repugnant is often measured in drops. A cocktail shouldn’t be too potent, too tart, or too sweet. If it has too little flavor the drink is perceived as lackluster; too much flavor and it becomes overbearing. The more attempts you make, the more respect you’re bound to develop for the cadre of drinks referred to as the Classics.

“In this age of microchips and nanoseconds, it’s difficult for some to see the relevancy of things deemed classics. Fortunately, that’s not the case with cocktails,” says Charlotte Voisey, noted drinks authority and brand ambassador with Wm. Grant & Sons. “Collectively they’re the foundation upon which all other cocktails are based. And let’s face it, these drinks have withstood the test of time because each successive generation has found them as irresistibly delicious as the one before.”

Adam Seger contends that a working familiarity of these drinks constitutes the beginning of a bartender’s transformation into a mixologist. A highly celebrated bar, and sommelier, and general manager of Nacional 27 in Chicago, Seger adds that gaining insight into the inner workings of the classic cocktails is the field-tested path to excellence behind the bar. “There are so many factors at play in a well-devised cocktail and it’s important for a mixologist to understand why certain dynamics succeed, while others don’t. For example, the Margarita works for essentially the same reasons the Sidecar does.”
The present generation of cocktails owes much of its resounding success to the structure, balance and timeless appeal of those that preceded them, and to the Principal Barkeeps who gave them life. And though you may not make these drinks every day, here are some sterling examples of cocktails that illustrate their points.

Aviation Cocktail
Cocktail glass, chilled
Pour ingredients into an iced mixing glass
1 1/2 oz. Plymouth Gin
1/2 oz. Luxardo Maraschino
1/4 oz. Rothman & Winter Crème de Violette
3/4 oz. fresh lemon juice
Shake vigorously and strain
Garnish with cherries

Combine all ingredients in an iced mixing glass, shake contents vigorously and strain into a chilled cocktail glass. Garnish with poached Maraschino cherries, which are poached in brandy, sugar, cinnamon/pear syrup and a whole vanilla bean.


Cinnamon Fig Sidecar
Sugar-rimmed cocktail glass, chilled
Pour ingredients into an empty mixing glass
1 black mission fig, diced
1 1/2 oz. fresh sour
Pinch of cinnamon
1 1/2 oz. VSOP Cognac
1/2 oz. Orange Curacao
Muddle ingredients and add ice
Shake vigorously and double-strain
Garnish with a fresh fig slice

Combine all of the ingredients in an empty mixing glass, muddle and add ice. Shake contents vigorously and double-strain into a chilled, sugar-rimmed cocktail glass. Garnish with a fresh fig slice.

Cavalier Cocktail
Cocktail glass, chilled
Pour ingredients into an iced mixing glass
2 tsp. apricot jam
1 1/2 oz. Remy Martin VSOP
1/2 oz. Cointreau

1/2 oz. orgeat
3/4 oz. fresh lemon juice
Shake vigorously and double-strain
Garnish with a lemon twist (discard)

Combine the ingredients in an iced mixing glass beginning with the apricot jam and shake vigorously. Double-strain the contents into a chilled cocktail glass. 
Express the essential oils of a lemon peel into the finished drink. Discard lemon twist before serving.

Kentucky Sidecar
Cocktail glass, chilled
Pour ingredients into an iced mixing glass
1 1/2 oz. Makers Mark Bourbon
1/2 oz. Marie Brizard Apry Liqueur
1/4 oz. Sonoma Co. Vanilla-Infused Simple Syrup
1 1/2 oz. fresh lemon sour mix
Stir until well chilled and strain
Garnish with an orange peel and a cherry

Combine ingredients in an iced mixing glass. Stir until contents are well chilled and strain into a chilled Martini glass. Garnish with a Maraschino cherry and quarter-size piece of orange zest. Express the peel’s essential oils into the finished drink.


Hemingway Cobbler
Collins glass, crushed ice
Pour ingredients into an empty mixing glass
2 grapefruit slices
2 lime wedges
3/4 oz. Stock Maraschino
1/4 oz. Luxardo Maraschino
1/4 oz. simple syrup
Muddle ingredients and add ice
2 oz. Appleton Estate White Jamaica Rum
Shake vigorously and double-strain
Garnish with a lime wheel and cherry

Combine the grapefruit, lime, liqueurs and simple syrup in an empty mixing glass, muddle ingredients and add ice. Pour in the white rum. Shake contents vigorously and double-strain into a Collins glass filled with crushed ice. Garnish with a lime wheel and cherry.


Radical-Free Raspberry Sidecar
Organic raw sugar-rimmed cocktail glass, chilled
Pour ingredients into an iced mixing glass
2 oz. V.S. Cognac
1/2 oz. Monin Organic Raspberry Syrup
1 oz. organic lemon juice
Shake vigorously and strain
Garnish with a fresh fig slice

Combine all ingredients in an iced mixing glass, shake contents vigorously and strain into a chilled cocktail glass. Garnish with a fresh fig slice.