Old-Fashioned-5England & America (mid 18th century)
Pendennis Club, Kentucky (1888)

The Old Fashioned is essentially The Original Cocktail, with roots going back to the mid 1700s at least. Back in the day, it could’ve been any kind of booze (in Wisconsin, they still do this one with brandy). Bourbon respects the drink’s established Kentucky roots.

Bitters are what makes this drink. Research into their history by David Wondrich and Brad Thomas Parsons indicates the first known bitters were patented in London in 1712 as a cure-all tonic to help settle the stomach. Roots, barks, spices, dried fruit peel, flowers, and just about anything else was fair game to be tossed in the pot along with grain spirit (to extract their essential compounds). These bitters would be combined with white wine or brandy, often taken as a hangover cure. Around 1750 or so, someone came up with the idea of adding a bit of sugar and water to make the mix more palatable. As these things tend to go, this combination spread to Colonial America as not just a healthy quaff, but a recreational delight. The word “cocktail” was first used in print in by the Hudson, New York newspaper The Balance, and Columbian Repository in 1806 to describe this trendy little number as such:

“Cock tail, then is a stimulating liquor, composed of spirits of any kind, sugar, water and bitters it is vulgarly called a bittered sling, and is supposed to be an excellent electioneering potion inasmuch as it renders the heart stout and bold, at the same time that it fuddles the head. It is said also, to be of great use to a democratic candidate: because, a person having swallowed a glass of it, is ready to swallow any thing else.”

All drinks using this template were called “Cocktail” for years and years. It would’ve been “Rum Cocktail” or “Brandy Cocktail” or “Whiskey Cocktail.” As the 19th century marched along and all kinds of new drinks emerged with unique identifying names (Martinez, Manhattan, Martini), people came to ask for this original version as the “Old Fashioned” cocktail. The bar at the Pendennis Club in Louisville, Kentucky helped standardize this name and recipe – specifying bourbon as the preferred spirit. As the century turned and Prohibition restricted access to “the good stuff,” people took to adding all kinds of adulterants to make the drink less awful: muddled oranges, cherries, lemons – even pineapple and mint on occasion. A drowning in seltzer was the final disgrace. And wouldn’t you know it, that formula stuck all the way through the next turn of the century, when people got their hands on copies of old 19th-century recipe books that called for the original, simple style of spirit, sugar, water (as ice) and bitters – with just a little hit of orange oil that perfectly unifies the caramel and vanilla of the bourbon with the holiday spices of the bitters.

THE KIT

Hardware: Jigger, Barspoon, Vegetable peeler or sharp knife
Ice: Ice rock or ice cubes
Glassware: Old Fashioned glass
Spirits: Bourbon whiskey – overproof (100 or more) stands up well (recommended: Bulleit, Four Roses “Yellow Label”, Wild Turkey)
Mixers & Liqueurs: Rich simple syrup (2:1)
Juices, Accents, & Garnishes: Angostura bitters, Orange twist, Orange wheel (optional), Cherry (optional) (recommended: Filthy amarena, Luxardo maraschino)

HOW TO

Using a vegetable peeler or a sharp knife, cut a strip of orange peel to make:

1 orange twist

Don’t include too much of the bitter white pith, if any. Holding the twist with the outside facing down over an Old Fashioned glass, pinch to express orange oil into the glass. Reserve the twist for a garnish. Into the glass, add:

3 dashes Angostura bitters
1/4 oz rich simple syrup

Add an ice rock or two to three ice cubes then add:

2 oz bourbon whiskey

Stir briskly to blend and chill. Insert the orange twist as a garnish.

Some people like an additional orange wheel and cherry garnish, some say all that does is take away from the whiskey. As you like it.

manhattan2New York City (1870s)

The Manhattan is where we start to get all fancy and what-have-you. Break out the cocktail glasses. If you don’t like whiskey, you’ll hate this one. And it could care less. Take it or leave it. The Manhattan is commonly made with bourbon, but the real authentic style is with rye. Check out how just two ingredients (whiskey and vermouth) take a couple dashes of bitters for a ride and create an amazing depth of flavor. Here’s where you’ll see why stirring spirits-only drinks makes a difference versus shaking. If you’re curious, try one shaken really hard so you can see the difference – and so you’ll know why to send one back if it’s made wrong.

Like many of our favorite drinks, the origin of the Manhattan cocktail is murky. I’ve heard stories:

  • 1846: Created by a bartender in Maryland to aid a wounded duelist (bullshit, vermouth wasn’t imported to the US prior to 1870)
  • 1860: Created by a bartender named Black near Broadway & Spring (bullshit, see above)
  • 1874: Commissioned by Winston Churchill’s mother at a Manhattan Club party celebrating the election of Governor Tilden (bullshit, she was in England at the time, eight months pregnant)

What we do know is this: vermouth hit the streets of New York City around 1870, and by 1880 it was the hot ingredient in cocktails. Taking the idea of the “improved” basic cocktail of spirit with sugar, bitters, and a touch of something extra, savvy bartenders nixed the sugar and “something extra” in favor of vermouth. They found the dry French kind paired well with gin (Martini, Turf Club) and the sweet Italian kind got along great with rye whiskey (Manhattan).

Vermouth is simply wine that’s been spiked with a spirit, usually brandy (“fortified”) and enhanced with a mix of botanical ingredients (“aromatized”). These botanicals may include wormwood, cinchona bark, gentian, cinnamon, citrus peel, lavender, saffron, vanilla, or dozens of others. Each vermouth maker has their own special blend. If you’re interested, read more about vermouth here.

The Manhattan most likely began as a 1:1 ratio of whiskey to vermouth, but I’ve also seen 2 vermouth to 1 whiskey in recipe books from that time. Somehow, over the years, the Manhattan has dodged a bullet and retained its respect, only occasionally dipping to a 2 whiskey to .5 vermouth ratio. That’s still the recipe most dive bars and restaurant bars use (they also will use whatever “well” bourbon is on hand – you really need a good rye here for spicy balance against the sweetness of the vermouth).

A properly-made Manhattan is truly a thing of beauty, capturing balance and brevity in four quick sips and priming your appetite for a great meal.

THE KIT

Hardware: Mixing glass, Jigger, Barspoon, Cocktail pick, Hawthorne strainer, Fine-mesh strainer
Ice: Ice cubes, Cracked ice
Glassware: Cocktail glass
Spirits: Rye whiskey – overproof (100 or 101) stands up well (recommended: Bulleit, Rittenhouse 100, Old Overholt)
Mixers & Liqueurs: Italian vermouth (recommended: Dolin, Noilly Prat, Martini & Rossi, Carpano Antica)
Juices, Accents, & Garnishes: Angostura bitters, Cherry (recommended: Filthy amarena, Luxardo maraschino)

HOW TO

Chill a cocktail glass in the freezer at least ten minutes.

In a mixing glass, add:

2 oz rye whiskey
1 oz Italian vermouth
2 dashes Angostura bitters

Add a mix of ice cubes and cracked ice to cover well above the liquid level. Stir well to blend and chill, then double-strain (to catch small bits of ice) into the prepared, chilled glass. Garnish with a cherry pierced on a cocktail pick.

Cuba-LibreHavana, Cuba (1900)
Townhouse Bar & Grill, Emeryville, CA (1995)

This spin on the Cuba Libre is one that can open the minds of your friends who don’t drink cocktails – except for Rum & Coke or Jack & Coke.

Coca-Cola was invented in the 1880s by John Pemberton, a pharmacist in Georgia. His product, originally called “Pemberton’s French Wine Coca,” was marketed as a patent medicine, a cure-all for various popular ailments including constipation, morphine addiction, impotence, and “extreme mental exertion.” Pretty sure its mix of Bordeaux wine, sugar, caffeine, and cocaine would put some pep in anyone’s step! Georgia enacted Prohibition laws in 1886 (trendsetters, way ahead of the national ban in 1920), so in order to keep his popular product moving, Pemberton reformulated his tonic to remove the wine, and it became even more popular.

But Coca-Cola seemed to be missing its booze, and eventually it found a natural companion in Caribbean rum. The original Cuba Libre goes back to just after the 1898 Spanish-American War in Cuba. U.S. soldiers stuck around and brought Coca-Cola with them, adding it to the typical rum and lime in an easy blend: a shot of rum, a squeeze of lime, top it off with Coke and toast with the battle cry of the day: “Free Cuba!” The Cuba Libre / Rum & Coke may be the most popular highball of all time, even inspiring a hit song in the 1940s (originally by Lord Invader, then covered by The Andrews Sisters). By this time, of course, the cocaine content in Coca-Cola had been nixed, just leaving the twin turbos of sugar and caffeine. And beginning in the ’80s, even sugar was booted in favor of the cheaper high-fructose corn syrup. Coke is still made with cane sugar in certain international markets like Mexico – read the ingredients list and look for “The Real Thing.”

Flash forward to the ’90s: Paul Harrington is working the bar at Townhouse up in Emeryville. He gets with two people from Wired magazine to launch a cocktail section on their web site (an incomplete archive by Robert Hess is here for the curious) that helps spur the current cocktail renaissance. His tweak to this tired old drink, suggested by a Venezuelan customer: Add a hit of gin and Angostura, cut back on the Coke – suddenly the high-school drink is all growed up. If you only know the standard version, you might be surprised by the magic that gin & Angostura work on the flavor: rounding down the sweetness and boosting the earthy spiciness.

THE KIT

Hardware: Shaker, Jigger, Barspoon, Straw (optional)
Ice: Ice cubes, Cracked ice
Glassware: Collins glass
Spirits: Light rum (recommended: Havana Club 3, Caña Brava, Cruzan), London Dry gin (recommended: Beefeater, Tanqueray)
Mixers & Liqueurs: Coca-Cola (if you can find imported Mexican Coke, your drink will be even better)
Juices, Accents, & Garnishes: Lime juice, Angostura bitters, Lime wedge

HOW TO

In a shaker about a third-full with ice cubes, add:

1 1/2 oz light rum
1/2
oz London Dry gin
3/4
oz lime juice
2 dashes Angostura bitters

Shake well to blend and chill, then strain into a Collins glass filled about two-thirds of the way up with cracked ice. Top with:

3 oz Coca-Cola

Stir lightly to blend and garnish with a lime wedge. Optionally, serve with a straw.