This is part of my Weekend Classics series of recipes that use entirely classic cocktail ingredients/methodology.

There’s sort of a progression that most cocktail lovers go through. First they probably start off with vodka. Your standard sweet, fruity, college kid drinks eventually give way to vodka martinis (extra dry, of course) shortly after you become of drinking age. Eventually you acquire the taste for rum and then gin, realizing that if you use good dry vermouth you don’t have to hide it as much as possible, and start drinking those instead.

Eventually you work your way around to whiskey. It probably starts with a sour then a Manhattan. And finally you work your way around to what is probably the first and arguably still the best cocktail ever made, the Old Fashioned.

What’s interesting about the Old Fashioned is it isn’t so much a cocktail as a template. The generally accepted version of an Old Fashioned today is a cocktail comprised of whiskey, bitters, sugar, and water. No more, no less. One could even argue that whiskey could be replaced by any liquor, as that was once the definition of a cocktail before the word was usurped. The original definition, from 1806:

Cock-tail is a stimulating liquor, composed of spirits of any kind, sugar, water, and bitters—it is vulgarly called bittered sling, and is supposed to be an excellent electioneering potion, in as much 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.

Eventually the word cocktail came to mean any mixed drink, much the same way “martini” has, over the last thirty years, come to mean anything served in a martini glass. Hence after it’s reinvigoration what used to be called merely a cocktail became an Old Fashioned Cocktail.

It’s natural for a newly-minted mixologist to try to make the Old Fashioned. What drink is sexier? It’s brown and served on the rocks, easily the most manly presentation of a beverage. There can be muddling. While Roger Sterling drinks Gibsons (basically a martini with an onion) and vodka on the rocks, Don Draper made an Old-Fashioned for Conrad Hilton.

One who is studious will find dozens of differing recipes for an Old Fashioned on the internet. People are very opinionated about it. Over the years I’ve tried nearly all of them in search for the perfect Old Fashioned. So I thought for this week’s classic cocktail I’ll break it down for you the way I like it best.

My one caveat here is that my goal isn’t to make the cocktail as close to the original version as possible. My general motto is “no sacred cows”. We of course want to stick close to the template. We could venture pretty far off of liquor, bitters, sugar, and water and make some great cocktails, but we might as well not call them an Old Fashioned when we do. I do, however, believe one should at least be open to the idea that someone came up with a better way to make a cocktail while remaining true to form in the last 150 years.

1. Liquor

I have had great Old Fashioneds made with rum and tequila, but for my money you can’t beat whiskey. But the question is, what whiskey? I tend to agree with Dave Arnold’s sentiment in Liquid Intelligence, use something tasty, high-proof, and not too expensive.

Dave recommends Elijah Craig 12, a fine bourbon for the buck, but for my Old Fashioned I like a good rye. Not one quite as spicy as an Old Overholt (which I love for Manhattans) but still with some kick. My favorite so far is probably Rittenhouse Bonded, which (like all bonded liquors) comes in at 100 proof. The extra alcohol helps as we’re going to dilute it a bit when we build. Shamefully I must admit I have not yet managed to acquire every quality whiskey on the market, so if you have a recommendation please do send it my way in the comments.

2. Sugar

For my money, nothing beats demerara simple syrup (1:1) for an Old Fashioned. Here’s probably my first and largest break from tradition. I don’t like sugar cubes. I realize that muddling them is sexy, but you get a cocktail that has little sweetness at the top and too much at the bottom. I want my drink to taste great 100% of the way through rather than 33%.

Plain simple is fine too. I’ll use a sugar cube if I have to, also demerara if available. But I’d pick plain simple over a demerara cube.

One needs substantially less sugar when working with simple because you don’t end up with half of it as a sludge on the bottom as you do with a cube. So I use one teaspoon (which is what most barspoons measure) of the stuff.

3. Bitters

Yet another (smaller) break with tradition. I use two dashes Angostura, one dash orange bitters. The orange adds an extremely complimentary flavor to the drink. Lots of people muddle oranges and cherries into the drink (I’ll get to that in a second) because the flavors meld so well with whiskey and sugar. I think it’s even more true of bitters.

4. Water

One does not need to add any water to an Old Fashioned. You see this often, and I think it’s a mistake. People often do this with a sugar cube, though even then I think the bitters are enough liquid.

When using simple syrup, you’ve already got over half a teaspoon of water. Also we’re building this drink in the glass, and a glass has a large thermal mass, which means more ice melts to get the drink to the same temperature. This is why you want a higher proof liquor to start with. If any water beyond what we’re starting with is added, I feel the drink becomes watered-down. Same if we stir rather than build, then add to a warm glass.

I also want this drink to stay on the warmer side. It’s best to think of an Old Fashioned as a slightly-adulterated straight whiskey, rather than a cocktail like a martini that you want served cold. For this reason I also don’t chill the glass before building and I don’t stir much when building. (If you like your Old Fashioned colder you can build it in a chilled glass and stir more to get similar dilution. That just isn’t my preference.)

So here’s my recipe:

1 tsp. demerara simple syrup (1:1)

2 dashes Angostura bitters

1 dash orange bitters

2 oz. Rittenhouse Bonded Rye

1. Add the simple, bitters, and 1 oz. of rye to a rocks glass.

2. Add about half the total ice you’d use for a whiskey on the rocks. Stir briskly three times.

3. Add the rest of the whiskey and the other half of the ice, stir another three times. Garnish with a cherry and orange flag.

4. Kick back and watch Mad Men, lamenting the boozy ending of the greatest drama on TV.

Modification: New Fashioned

For the last couple decades, it has been popular to muddle the cherries and oranges into the drink. This is quite delightful, but I feel falls outside of the definition of an Old Fashioned. At the bar I work at we call it a New Fashioned.

The process is mostly the same, with the exception of a muddling step. Here’s how I do it.

1. Peel an orange wedge, reserving the peel. (I’d say we’re using about 1/6th of a small orange here, or 1/8th of a large one. I am sorry there aren’t more precise measurements for citrus wedges.)

2. Place bitters, sugar, two brandied cherries, and the peeled orange wedge (we don’t want to muddle the pith in) in a rocks glass and muddle.

3. Add one ounce of the whiskey, half of the ice, and then proceed as in the Old Fashioned.

4. At the end, twist the peel over the drink and wipe the rim with it. One needs no garnish with the New Fashioned.