In the pantheon of cocktails, there is one undisputed grandaddy of them all—the namesake for the term “cocktail”—the old fashioned. The formula is quite simple, and yet unlike anything that came before it.

The cocktail, originally defined as a combination of alcohol, sugar and bitters, is now more than 200 years old. In the early days, the cocktail could be ordered with any base spirit. There was the whiskey cocktail, the gin cocktail, the champagne cocktail (this one kept “cocktail” in the name). When “newer” drinks became popular—the sour (alcohol, sugar, citrus), the fizz (alcohol, sugar, citrus, seltzer), the daisy (alcohol, liqueur, sugar, citrus, seltzer), and so on—a new nickname for the most popular of the first generation cocktails was coined. Whiskey with sugar and bitters became “the old fashioned.”

My obsession with cocktails began long before I started tending bar professionally. The old fashioned, the sazerac, the martini—these were focal points of my early 20s. I bought books and scoured the internet for the history of these classics on my quest to master them. Cobbling together information on how to stir and make syrups and what kind of bitters I should buy, I finally ended up making the old fashioned I had seen in movies and read about in books like John Updike’s Rabbit, Run.

I muddled some cherries and orange wheels and threw in some sugar. I didn’t exactly know what a “dash” of bitters was supposed to be, but I went for it anyway. I remember seeing soda water added in most iterations. This was the drink that was most pleasing to my young palate.

I have given the better part of a decade to cocktails and cocktail bars, and I have since learned that the old fashioned I enjoyed making and drinking more than 10 years ago is not exactly true to the primordial old fashioned.

Picture a nicely etched glass, a huge, clear block of ice and a large strip of orange peel. This clean, elegant version of the old fashioned is primarily found in cocktail bars, and in my experience, it’s a litmus test for cocktail enthusiasts.

The continued evolution of the old fashioned can be tasted at Haberdasher. Previously known as Single Barrel, it lays claim to the title of first craft cocktail-focused bar in San Jose, and owner Cache Bouren has put the old fashioned on tap. After finding the right proportion of whiskey, sugar, water and bitters, the crew at Haberdasher is able to pour the classic in a fraction of the time it would normally take a barkeep to mix one.

Bouren says the process provides consistency and convenience, but also creates a talking point around the drink. Far from cheapening “the king of cocktails,” as Bouren calls the old fashioned, his process pays homage to the drink; it is now perfect for all who order it. I agree with his reasoning.

At Trials Pub, you can find what I would call an “old school” or perhaps mid-century take on the old fashioned. I’ve had many here since I was 22, so I know it’s the best counterpoint to the “craft cocktail” rendition. Thane Ferguson, bartender at Trials, has a particular connection to the drink that’s tied to nostalgia. His great-grandfather drank old fashioneds, Groucho Marx drank old fashioneds, his older brother drank old fashioneds. For 20 years, Ferguson has prepared this cocktail in a very specific and distinctly layered way. Muddle a cherry and orange wheel with a sugar cube. Add bitters, then ice, then whiskey. When served, the guest can stir the drink up to dissolve the sugar if they want it sweeter, or sip off the top for more bite.

Due to its long history and the ebb and flow of quality in bars over the decades, the old fashioned has many variants. To some, the muddled simplicity that was popular in the ’50s and ’60s is the true old fashioned. For many in the Midwest, the brandy old fashioned is a cultural mainstay. For the modern cocktail enthusiast, it’s a clean drink over a large block of ice. All delicious when made with a little bit of care.

‘Old School’ Old Fashioned

  • 2 oz whiskey
  • ¼ oz simple syrup
  • 3 dashes bitters
  • 1 maraschino cherry
  • 1 half-wheel orange slice
  • seltzer

In a rocks glass, muddle cherry, orange, bitters, and syrup. Add ice, then whiskey. Briefly stir. Top with ice and a splash of seltzer.