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.

negroniFlorence, Italy (1919)

A classic cocktail with a surprising number of devotees, the Negroni is distinguished by its use of Campari, the bitter-orange aperitif that is – to put it kindly – an acquired taste. But I’ll say this: once you do acquire the taste, there’s no going back.

The Negroni is a great appetite stimulant – perfect before a big dinner. It works equally well on the rocks (in spring and summer) or up (in fall and winter). You’ll want a good, sharp, juniper-forward gin here – one that won’t get beaten down by the other two bullies in the drink.

The drink has an interesting origin story: Italian-born Count Camillo Negroni had spent time in America as a cowboy and in London as a bon vivant. On his return to Florence in 1919, he asked the bartender at the Caffè Casoni for a stronger take on the popular Americano cocktail, swapping gin for soda water, and serving it up (or on the rocks). It caught on locally, and his namesake cocktail became a hit internationally. Anthony Bourdain is on record as a fan; Gaz Regan is famous (infamous?) for his “finger-stirred Negroni.”

There’s something magical about a well-made Negroni: it’s like a reset button for your day, signaling the start of a great night when anything is possible.

THE KIT

Hardware: Mixing glass, Jigger, Barspoon
Ice: Ice cubes
Glassware: Cocktail glass (or Old Fashioned glass)
Spirits: London Dry gin (recommended: Beefeater, Tanqueray) or Plymouth gin
Mixers & Liqueurs: Italian vermouth (recommended: Carpano Antica, Noilly Prat, Dolin), Campari
Juices, Accents, & Garnishes: Orange twist

HOW TO

Chill a cocktail glass (or Old Fashioned glass) in the freezer at least ten minutes.

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

1 oz gin
1 oz Italian vermouth
1 oz Campari

Stir well to blend and chill, then strain into the chilled glass. As an alternative, this drink may be served in an Old Fashioned glass over rocks.

Pinch an orange twist over the drink to express oils onto its surface, then rub the twist around the glass rim to coat. Garnish with the twist laid across the surface of the drink.

nuinuiDon the Beachcomber (1937)

File under “semi-obscure-but-completely-delicious.”

When Don the Beachcomber moved into an expanded location across the street from their original spot in Hollywood, they also expanded the drinks menu. The “Pupule” was one they added to the lineup – another dimensionalized riff on the Planter’s Punch, this time mixing orange and lime for the sour element, and merging sweet and spicy with flavors of allspice, vanilla, and cinnamon. I imagine Donn’s customers had a good number of juvenile laughs at the name (Poo Poo? Purple? Pustule?) before he changed it to “Nui Nui” around 1941 (much better, it means “Big-Big” or “Extra-Large” in Maori).

In spite of the boastful name, booze-wise this drink is no big deal. Same amount of rum as a little Daiquiri – but they still enforced a three-per-customer limit on this one. Most likely to appeal to the macho types who felt their masculinity threatened by all the orchids and whatnot. “Are you man enough to handle three of these?” and so on.

A note on orange juice – lemon and lime juice is always fresh in these recipes, but it’s easy to assume that pasteurized orange juice from concentrate, the breakfast staple, is the same thing as fresh-squeezed. Short answer: it ain’t. You gotta squeeze an orange, sorry. But before you do, prepare the garnish, a long orange peel – like a whole orange peeled all the way around and around with a Y-peeler. Feel free to use whatever size peel you like and decorate as you prefer: the original hung the peel out of the drink and down the side of the mug or glass; I like coiling it up like a crown and loading with more ice.

You’ll need three syrups or liqueurs for this: pimento dram, cinnamon syrup, and vanilla syrup – see recipes here if you’re up for the effort (and the necessary time) to make them yourself at home… but a great alternative is BG Reynolds‘ fantastic line of tiki syrups from Portland, Oregon.

If you’re going through all the fun to make this fantastic drink, why not serve it in a vintage tiki mug? Great finds can be had at thrift stores occasionally, or check online at Etsy‘s vintage shops.

THE KIT

Hardware: Electric blender, Jigger, Straws (optional)
Ice: Cracked ice
Glassware: Tiki mug or Collins glass
Spirits: Amber rum (recommended: Cruzan Aged Dark – or Havana Club Añejo Especial if you can get it)
Mixers & Liqueurs: Pimento Dram, Vanilla Syrup, Cinnamon syrup
Juices, Accents, & Garnishes: Lime juice, Orange juice, Angostura bitters, Orange peel

HOW TO

In an electric blender, add:

2 1/2 oz amber rum
3/4 oz lime juice
3/4 oz orange juice
3/4 oz cinnamon syrup
1 tsp vanilla syrup
1 tsp pimento dram
1 dash Angostura bitters
3/4 cup cracked ice

Flash blend five seconds to quickly mix – meaning just turn the blender on, then off again. Pour unstrained into a tiki mug or Collins glass. Garnish with a long orange peel. Optionally, serve with two straws.