This is my longtime favorite cocktail, and my dad’s favorite too — it’s the one he first taught me to make. When I was a kid, if I was lucky and if he was in a generous mood, I’d get to make this for him when he got home from work. Ah, a quality New Orleans upbringing — you teach the kids the important stuff early.

The popular myth in New Orleans is that the Sazerac was the first cocktail, but if any case or argument can be made for anything being “the first cocktail,” it’s the Old Fashioned.

As you may be aware, the first published definition of what a cocktail (“cock-tail” or “cock tail”) was appeared in a Hudson, New York newspaper called The Balance and Columbian Repository, in a reply to a letter to the editor on May 13, 1806. After a local Democratic candidate lost his bid for office, the paper published a humorous account of his Loss and Gain; in the gains column was “NOTHING,” and in the losses column there were “720 rum-grogs, 17 brandy do., 32 gin slings, 411 glasses of bitters, 25 do. cock-tail and My Election.” A reader wrote in to inquire as to what this “cock-tail” actually was, as he’d never heard of it. The editor replied,

As I make it a point, never to publish anything (under my editorial head) but which I can explain, I shall not hesitate to gratify the curiosity of my inquisitive correspondent: 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. — Edit. Bal.

See, political snarkiness in the press is far from a modern phenomenon. But there it was.

Spirits, water, sugar and bitters. If you combine the sugar and water into simple syrup, for convenience and to keep any sugar grit out of your drink (because who wants that?), then you’re down to spirit, simple syrup and bitters.

If your spirit is whiskey, then this drink was called a Whiskey Cocktail.

There are origin stories of the Old Fashioned that claim it was invented at the Pendennis Club in Louisville, Kentucky in the 1880s. This is highly doubtful, given that the drink with the exact same ingredients had been swilled for at least 74 years before that, and probably a lot longer. A more believable origin story is that when bartenders like Professor Jerry Thomas started introducing far more cocktails and mixed drinks of all kinds into the American drinking repertoire, especially those involving exotic-at-the-time ingredients like vermouth, those who wanted a good ol’ whiskey cocktail took to asking for it old-fashioned style, an Old Fashioned Whiskey Cocktail.

It was around 1936, if I recall correctly, that the Old Fashioned began its downfall — not because it was a bad drink, but because it started to be made in variations that I just consider to be unworthy.

If you have some time, read Robert Hess’ marvelous article tracing the development of the Old Fashioned, “Renewing an Old Fashion.” For years Robert had the same problem I did — he had a very hard time ordering a decent Old Fashioned at a bar.

They kill it with soda, they leave out the bitters, the grind an orange slice into a disgusting paste, they muddle the fake cherry, for God’s sake. Robert’s essay traces the drink’s history and development, and the proper way to make it (as well as how not to), including recipes from over two dozen sources, some going back over a century.

I’m going to print a few of these out and stick them in the trunk of my car. Next time some bartender tries to insist that the crappy watered-down Bourbon spritzer with a shredded cherry and a mess of finely ground fruit paste he’s just served me is a “traditional Old Fashioned”, I’m going to politely excuse myself, go to my car, fetch the papers, go back to the bar and present them to the bartender with my compliments.

It’s fascinating reading, but if you don’t have the time to go through the whole 36 printed pages’ worth, learn from this:

For myself, the key concepts I think are important to the Old Fashioned are as follows:

Water is only intended to aid in the dissolving of the sugar, and should be kept to a bare minimum. In fact, it can be omitted entirely if you use simple syrup.

A fresh slice of orange, when muddled in the drink at the beginning, adds some interesting and useful flavor notes that play nicely against the bourbon or rye.

A cherry adds a nice visual touch when used as a garnish at the very end, but is nothing but an ugly mess when its crushed carcass lies at the bottom of your glass.

Soda water has no place in this drink. Ever.

Yeah you rite. However, I have to say that I am a purist and I do not care for the muddled orange slice. Yes, I know this puts me at odds with Gaz Regan and Dale DeGroff, but that’s the way my dad taught me to make it, as a true old-fashioned whiskey cocktail: whiskey, sugar, water, bitters. I do like a large swath of orange peel in it, though, either gently muddled or (preferably) with the oil expressed over the top.

I will drink an Old Fashioned in which an orange slice has been GENTLY muddled, removed and replaced with a fresh slice for garnish, but I have never actually seen anyone do this outside of a top professional like Dale or Gaz doing it at a demonstration. 999 times out of 1000 the orange slice is ground into a purée, and gives the drink, for me, a disgusting consistency.

I make Old Fashioneds in myriad ways — different combinations of bitters, different whiskies, different spirits even (I adore Rum Old Fashioneds, Añejo Tequila Old Fashioneds and Mezcal Old Fashioneds). Here’s my “standard,” though, which is a winner.

The Old Fashioned Cocktail
(Chuck’s standard version)

2-1/2 ounces rye or Bourbon whiskey.
1 teaspoon rich simple syrup.
2 dashes Angostura bitters.
1 dash Peychaud’s bitters.

Build in and Old Fashioned glass, add ice to fill and stir for 20 seconds. Garnish with a Bourbon-soaked or brandied cherry, and/or a piece of orange or lemon peel.

Let’s watch master New Orleans bartender Chris McMillian make one.

Chris is The Man here … no club soda (the ruination of any Old Fashioned) and no muddled fruit (I want a strong whiskey cocktail, not a puréed fruit salad). I do like the orange peel in it, though, and I often like Peychaud’s bitters in addition to or instead of the Angostura (I got that from my dad; Peychaud’s was always his favorite).

Most if not all whiskey-based Old Fashioneds you order now (if you can even order one and get it made properly) are going to be made with Bourbon, but if you really want to make this drink great make it with rye.

I occasionally like to make what I call a “Houlihan Old Fashioned” or a “Hot Lips Old Fashioned.” I was watching an episode of “M*A*S*H” once, one of the episodes later in the series when Margaret Houlihan stopped being a one-dimensional ninny and foil to Frank Burns, and started to be developed into a more complex and human character (whom I liked very much). She was in the officers’ club, went up to the bar, and ordered her favorite drink — firmly but politely, and with a tiny grin and a twinkle in her eye…

“Old Fashioned. Straight up. No fruit.”

Margaret was awesome.

[The first version of this article was published on September 8, 2000 and was revised on April 13, 2002; August 24, 2007; and February 4, 2010.]