The Old Fashioned is a classic drink.  It's one of the oldest cocktails, which, yes, led to the name.  If you walked up to a bar in 1840, this is what you might get if you just ordered a "cocktail."  Back then, you could specify your spirit, and there was an entire world of different types of bitters that might be used.  Depending on when and where you were, you might get a little absinthe or other liqueur in the drink, and there was probably some orange involved somewhere.  Bar books in the late 1800s began specifying some version of that as an "old fashioned whiskey cocktail," and the name entered common parlance together with various versions of the recipe.

 

Lately, by which I mean in the past 80 years, the Old Fashioned recipe has become somewhat codified as rye or bourbon, a bitters-soaked sugar cube, muddled orange, and a maraschino cherry.  Old Fashioneds made thusly can be fine.  But they aren't great: the muddled orange slice usually falls apart and junks up the drink; the maraschino cherries (in spite of my questionable and possibly unhealthy desire to eat them straight out of the jar) aren't any good in a sophisticated cocktail; the sugar doesn't dissolve, leaving a grainy residue; and bartenders who learned their trade from Tom Cruise movies shake the drinks to mix them, leading to bits of broken ice in the drink.  None of that is any good.

 

We can fix all of that.  Read on for the steps.  It's a very simple process, but I'll explain a few things along the way.

This version of an Old Fashioned will let the clarity of your bourbon shine through, gently mellowed with the warmth and sweetness of orange and sugar.  It will not feature mangled orange bits, candy-red cherries, or icy slush.  We'll go piece-by-piece, then assemble the whole thing.

 

Orange flavor is a big part of a Old Fashioned.  The traditional way to get that is to muddle orange with a sugar cube and a bit of water.  We're going to bump up the orange flavor a bit and remove some of the troublesome parts by combining all of those into a single step to make orange-flavored simple syrup.  Not familiar with simple syrup?  It's a 50/50 mix of sugar and water, which works well as a sweetener because the sugar is pre-dissolved.

 

Start by zesting an orange. Microplane-type graters are by far the best choice for this; the one linked here is just about the best.  Place the zest in a bottle that you can seal -- a wide-mouth Nalgene or other sports bottle works well for this, or a wide-mouth Mason jar (choice of color!) is good, too -- then add one cup of water, one half-cup of white sugar, and one half-cup of brown sugar.  Shake the mixture until the sugar is dissolved -- about four or five minutes -- then put it in the refrigerator for 8-12 hours.  Strain out the orange zest, and you're good to go.  The simple syrup will last about a month. 

Once you have some cold simple syrup, you're ready to mix the drink.  Start by gathering the rest of the ingredients.

• Whiskey.  If you're not familiar with different types of whiskey, start with a decent bourbon.  Weller is my favorite inexpensive one; Jack and Jim are OK.  Evan Williams will also do the job.  Nicer is better, but don't use your best stuff, either, because you ARE going to be adding a fair amount of sugar to this.  That said, definitely use something you can sip.  If you can't do that, you won't like your drink, either.  Feel free to experiment with rye and other whiskies, but Scotch does not work.

• Angostura bitters

• An orange.  This is for the garnish.

• Ice.  Cubes are best.  Make sure they're fresh, please.  Old ice can ruin the drink because it can pick up flavors from the freezer which can be transferred to your drink.  Subtle hint of freezer-burned ground beef in your drink?  Bleh.

You'll need some version of all of these, but you certainly don't have to go buy everything I've linked to make this drink.  So long as you can accomplish the steps in the mixing process without compromise, use what you've got.  But don't cheat, or else your drink will suffer.

• Mixing beaker or other container (I usually use a pint glass)

•  Measuring cup or jigger

•  Eyedropper.  More on this later.

•  Stirrer.  If you don't want to buy a proper bar spoon, use a table knife, not a regular spoon.  

•  Strainer.  Or be creative.  The strainer in the link is a julep strainer, which works well here because all we need to do is hold back some ice.

•  Coupes.  Hit the thrift store for something attractive, delicate, and relatively small.  Or you could use any number of other types of glassware.

•  Channel knife.  We'll cut a decorative strip of orange with this.

Once you've got all of that, we're ready to go.  First, put your glassware in the freezer.  All of it.  Go away for a while; maybe 10 minutes.  The glasses need to be cold.  Ordinarily, Old Fashioneds are served on the rocks, but we're going to take care with how we do this so that we don't have chunks of ice diluting our drink.

 

Assembly is pretty easy.  For each drink you make, here's what you need:

• Two ounces of whiskey

• 3\4 tablespoon of orange-infused simple syrup

• Two drops of bitters, dispensed using the eyedropper

 

Combine all in your (cold) beaker with perhaps 4-5 cubes of ice, or whatever fits.  Use the stirrer to, well, stir.  Keep stirring.  If you want a cold drink -- and you do -- then you need to stir vigorously for about 60 seconds.  Seriously, keep stirring.  Done?  OK, grab your glasses from the freezer.  Use the strainer and pour the chilled mixture into your glasses.  Done?  No, you're not.