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Drinks Pairings

Whiskey Cocktails: The Manhattan, Old-Fashioned, Sazerac and Mint Julep

Aug 9, 2013 | By Jack Bettridge
Whiskey Cocktails: The Manhattan, Old-Fashioned, Sazerac and Mint Julep

When it's mixing time, American is the natural choice in whiskey. Not only does the notion get history's endorsement—the cocktail was born in the U.S. of A.—but American straight whiskeys-Bourbon, rye and Tennessee sour mash-all have deep, bold flavors. The better for standing up to all manner of sweeteners, liqueurs, aperitifs and bitters.

They also play well with strangers, allowing a synthesis that is greater than the sum of the parts. New flavors seem to be unveiled as they work their magic on whatever is added. And every brand name, every label, seems to spawn a different drink when mixed into the same formulation.

Furthermore, American whiskeys are unafraid of the deep end. They take the plunge in all manner of effervescence—from club soda to ginger ale, bitter lemon to cola—and their charms bob right to the surface. Nor will fruit juices and fruit proper scare them off.

The great drinks that start with patriotic fuels would fill a book. Here are some of the classics.

The Manhattan

The prototype vermouth-and-spirits cocktail, the Manhattan is also the standard against which all other creations are judged. From its basic formula marched a parade of classics: the Martini (gin or vodka, now mixed with dry vermouth) the Rob Roy (Scotch whisky, with sweet vermouth), the Metropolitan (brandy and vermouth). Moreover, the Manhattan has emboldened an army of bartenders to try every manner of aperitif and liqueur with every kind of spirit. It deserves its own wing in the Drinking Hall of Fame.

It's a great a story that the first Manhattan was made for Winston Churchill's mom, but sadly it's just that: a story. Invented around 1870, the drink started as a rye-based cocktail and later morphed into a Bourbon drink. Either way it perfectly bespeaks the New York City borough for which it is named. It's a compact mix that vibrates with dozens of flavors and energy, a melting pot of a cocktail. Whatever whiskey you choose, think out the spirit-to-aperitif ratio based on the brand. Each one creates a markedly different cocktail.

Stir or shake according to your own taste. Stirring results in a clearer drink. But if cold and frothy is what you want, shake. The less traditional, shaken version was the choice of both Bart Simpson and The Thin Man's Nick Charles (his to a fox-trot rhythm). You can also dispense with the pitcher and shaker altogether and mix it on the rocks in an Old-Fashioned glass or, as Marilyn Monroe did to great effect in Some Like It Hot, in a hot water bottle. The mix got cold, but the scene stayed hot.


The whiskey-vermouth proportion is only a guideline. Take it up to 5:1 if you want. Rule of thumb: Use more whiskey when it's sweeter or low-proof; less when it has spice, a bite or high-proof.

2 ounces Bourbon, Tennessee or straight rye whiskey
1 ounce sweet vermouth
2 dashes bitters
1 maraschino cherry

Pour whiskey, vermouth and bitters over ice in a shaker or pitcher. Shake or stir. Strain into a cocktail glass. Garnish with the cherry.

Note: The drink becomes a Perfect Manhattan when sweet and dry vermouth are mixed, a Dry Manhattan when you use only dry vermouth. It can also be endlessly varied with different aperitifs, bitters and garnishes.


Deep into the screwball comedy of the 1963 movie It's a Mad, Mad, Mad, Mad World comes a scene in which Jim Backus, as a besotted pilot, asks non-flier Buddy Hackett to take the controls so he can make "an Old-Fashioned the old-fashioned way." Hackett worriedly replies, "What if something happens?" To which Backus answers in his best Larchmont lockjaw, "What can happen to an Old-Fashioned?"

Apparently a lot.

Originally it was styled a Whiskey Cocktail, a simple mix of spirit, sugar and bitters. Then came the rococo post-Civil War era of drinking, when bartenders fell to bombarding concoctions with syrups, cordials and fruit juices. Patrons who favored a return to a less bumptious cocktail—one that hewed to the original definition from the beginning of the century—would ask for their drink served the old-fashioned way, and the Whiskey Cocktail was renamed the Old-Fashioned.

Later it became more specifically a Bourbon drink—as in the one made at Louisville's Pendennis Club. Now you'll typically see it tricked out with fruit. Purists may complain, but it makes for a great drink.

When you think about how long the Old-Fashioned has been around the name makes sense. Fittingly the cultural references abound: from Huck Finn describing (but not naming) it, to Updike disparaging it, to Don Draper demonstrating it on "Mad Men."

Place the syrup, bitters, cherry and orange in an Old-Fashioned glass, and muddle to a paste. Add large ice cubes and the Bourbon. Stir well. Variations include experimenting with fruit (lemon and lime, of course, or even pineapple) and leaving out the muddling step. Add seltzer water if you want fizz.

The Sazerac

Originating in New Orleans, the Sazerac wasn't born American. It's ancestor was made of Cognac and Peychaud's bitters. After the Civil War and the phylloxera infestation conspired to shut down imports of French brandy, rye whiskey stepped in and was joined by absinthe (so the cocktail could still claim a Gallic heritage).

Even though O. Henry drank gobs of them when he installed himself in New York City, the Sazerac will forever be the official New Orleans cocktail, with its links to characters such as Huey Long and Tennessee Williams. Oddly, it gets a lot of play with fictional spies. W.E.B. Griffin's Cletus Frade of the OSS took them with oysters.

When James Bond visits New Orleans in Live and Let Die, CIA sidekick Felix Leiter goads the consummate Brit into sampling the local tipple, asking, "Where is your sense of adventure?" Of course, 007 takes one. A Gin & Tonic would have blown his cover.


This drink has evolved so much that it's now hard to call any version authentic. For old time's sake, try it at least once with Cognac in place of rye.

1/2 teaspoon absinthe or pastis
1 sugar cube
2 ounces straight rye whiskey
4 dashes Peychaud's bitters
1 lemon twist

Coat an Old-Fashioned glass with absinthe. Pour the excess absinthe back in the bottle, and place the glass in the freezer. Muddle the sugar cube with a little water in a mixing glass. Add some ice cubes, the whiskey and bitters to the mixing glass. Stir. Retrieve the glass from the freezer, and strain the contents of the mixing glass into the Old-Fashioned glass. Twist the lemon over the glass, and use for garnish or discard.

Note: Peychaud's is the bitters to use. Angostura, for its part, has the good grace to not even mention the Sazerac on its company's website.

Whiskey Sour

Just like movie and book storylines, cocktails can be boiled down to a few basic scenarios. The characters (read: ingredients) may change, but the plot stays the same.

One that gets used over and over (perhaps because it's so good) is called the Sour. And it goes like this: spirit meets citrus juice, they fall in love and live happily ever after.

The list of titles goes on and on: from Daiquiris and Fizzes to Greyhounds and Screwdrivers. The Whiskey Sour is one of the earliest—and best. Some recipes, dating to the 1870s, call for lime juice, but really lemon is perfect for tarting up whiskey, and that's the modern standard.

Some would attack the Sour as rather wimpy (in The Seven Year Itch, Richard Sherman suggests it's a breakfast drink). But when Raymond Chandler puts one in the hands of heavy Moose Malloy (the name explains it all) in Farewell, My Lovely, the hard-bitten private dick Philip Marlowe doesn't flinch.


The reason we don't use crushed ice—as in a slushy—is that it melts too quickly and ruins the proportions. The reason we don't use pre-made, powdered mixes is that they suck.

1/2 ounce simple syrup
1 ounce fresh lemon juice
2 ounces Bourbon, Tennessee or straight rye whiskey
1 tablespoon egg white (optional)
1 maraschino cherry
1 lemon slice

Combine syrup, lemon juice and whiskey over ice in a shaker glass. Shake for 15 seconds. To achieve a fizzy froth, add the egg white and shake until your arms tire, then shake some more. Pour in a cocktail glass. Garnish with the cherry and lemon slice.

Note: Those who cook their own simple syrup can make this drink a little livelier by muddling tarragon or basil leaves in with the sugar and water.

Mint Julep

We all know that the Mint Julep is the official drink of the Kentucky Derby, but don't limit this drink. Its geography covers the entire South (and really we're all south of somewhere). And it's in season whenever mint grows—whether there's a horse race going on or not.

What makes this quaff gallop is that it layers bracing aromas, whiskey's bite and soothing sugar all on a bed of ice chips. Originally Juleps raced with any manner of spirit, but Bourbon eventually got the inside track with its corn-based sweetness.

You can make them up North, but be forewarned, Johnny Reb will never approve your results. This contempt has been going on for a long time. When H.L Mencken, from the border state of Maryland, made them with rye instead of Bourbon, columnist Irvin S. Cobb sniffed that the result was like putting "scorpions in a baby's bed."

But Southern folk nevertheless love to share their pride. Kentucky's Henry Clay made Juleps a national panic when he brought them to Washington, D.C., in the 1850s. Faulkner may have used them to fuel his protracted sentences, but most Southerners see fit to limit consumption. At least, that's the musical warning behind the Clovers' hit "One Mint Julep."


One point of contention is the proper sugar source. We think simple syrup (boiled sugar and water) mixes better than granular types.

1 dozen mint leaves
1 tablespoon simple syrup
2 dashes Angostura bitters
2 ounces Bourbon or Tennessee whiskey

Place the intended serving vessels in the freezer at least half an hour before post time. Combine half the leaves with the syrup and bitters in a mixing glass. Gently muddle (crushed leaves reveal a bitter side). Add the whiskey, and muddle some more, while stirring. Retrieve the glasses from the freezer. Fill them with crushed ice, and pour the mixture in. Garnish the mouth of the glass with the remaining mint. Serve with napkins.

Note: While crushed ice can ruin many drinks, it's perfect here as it melts quickly and cuts the unmitigated alcohol dose. Silver or pewter cups are traditional, but short, chimney-shaped highball glasses equipped with short straws do just as well at funneling the mint bouquet to the nose.

Whiskey Cocktails Bourbon

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