Of all of the truly classic cocktails available to the modern drinker, few are as venerable as the Old-Fashioned. The drink itself is close to 200 years old. Back then, if you wanted one, you would ask the barkeep for a whisky cocktail.
Back then, the term "cocktail" had a much more specific meaning than it does today. A cocktail was a drink consisting of spirits, bitters, sugar, and a little bit of water. It's sort of like how a martini was once a drink with gin, vermouth, and a dash of orange bitters, but these days includes any stiff drink served straight up in a martini glass.
Through the years, people would add various liqueurs to the drink. For example, if you use Peychaud's bitters and add a few drops of absinthe, you're well on your way to making a New Orleans classic, the Sazerac.
Since there were all of these new-fashioned drinks popping up, anyone who wanted one of the original style drink would ask for an old-fashioned cocktail. Through time, the term "cocktail" came to mean any drink with multiple ingredients including at least one hard liquor.
One small variation to the Old-Fashioned has hung on: A strip of orange zest gets muddled into the drink. Over time, that has somehow evolved into taking the garnish (an orange slice and a maraschino cherry), and muddling the whole thing right into the drink.
If you're doing that to your Old-Fashioneds, I have some simple advice.
Please stop that right this instant.
Muddling the orange slice and cherry does no favors to the drink. It looks terrible, the pith adds unwanted bitterness, the little mashed up bits of fruit get stuck in the straw, it's just a mess all around.
How do you make an Old-Fashioned the right and proper way? It's easy. Take a strip of orange zest (without the pith) and put it in a glass. Add one sugar cube (not simple syrup; the solid sugar abrades the orange zest and helps express the essential oils). Dash a couple of dashes of bitters into the glass, preferably right into the sugar cube to help the sugar dissolve just a little bit.
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Then, muddle the contents of the glass thoroughly. Add your liquor of choice (I usually reach for a nice spicy rye whiskey) and some ice cubes (or one really big one if you have those available). Swirl the drink a few times to melt the ice just a skosh, and enjoy. Simple enough.
Old-Fashioned 1 wide strip orange zest 1 sugar cube (or 1/2 teaspoon sugar) 2 dashes bitters (preferably Angostura) 2 ounces rye or bourbon whiskey
Muddle orange zest, sugar, and bitters in a double rocks glass. Add whiskey and a few ice cubes. Stir gently to combine. Garnish with an orange slice and maraschino cherry if desired.