In 1880, a decade marked by economic prosperity and innovation, James E. Pepper changed the world, perhaps forever. It was at the The Pendennis Club in Louisville, KY where it happened. Pepper took a lump of sugar, Angostura bitters and some whiskey and created The Old Fashioned Cocktail hereafter known as an old fashioned.
If you are one to imbibe, with a penchant for spirit forward beverages, you've undoubtedly heard of this drink and likely had an excellent one at a favored cocktail bar. No sooner than your next outing, you've probably had a bad one, and perhaps it looks completely different, for some reason pink in color with pulp floating in it. Sure, you're not one to complain, but you know that you deserve better.
Well I am here to give you what you deserve, in perpetuity. I am going to teach you how to make the perfect old fashioned. I share with you the details that make an old fashioned incredible. I explain all of what those fancy cocktail recipe websites don't tell you. Please pay attention, and follow every step closely. Each step matters and I won't waste your time with minutia if it does not add something to the finished product. If you would like to cut to the chase, you can go to liquor dot com or many other places on the internet, but if you want to know how to impress every tailored suit clad businessman that ever sets foot in striking distance of your bar cart, stay put, and keep your eyes on this screen. Take notes, and bookmark this page if you need to. I've fully illustrated the process for greater clarity and bartending accuracy. Here we go.
The first thing you need to do is have the right tools. No matter how thirsty you are right now (thirsty for a first class cocktail experience ). A quality axe cuts a better log and barmanship is no different. Please budget for premium results. You'll need the following items:
A Mixing Glass. Contrary to popular belief, a shaker is not going to come in handy for this spirit lead beverage. You'll need a 24 ounce tempered stirring glass with a spout poised for smooth dispensation of your mixed drink. These can be difficult to find at traditional department stores. Pull out the credit card and visit a place that can provide you top notch kitchen and bar ware or find quality mixing glasses online.
A Bar Spoon. It's easy to come by a bad bar spoon, just as it's easy to find a bad bartender. What you're looking for is a stainless steel spoon that has some weight to it, not sheet metal that has been stamped out. The best quality spoons will have a small scoop, a twist pattern to the handle, and a little extra weight at the top. This helps with the comfort and efficiency of the stirring process.
A Jigger. Accurate measures are essential in bartending, and the industry forefathers have created a measuring device specifically for their line of work. A jigger has two cone or semi-spherical cups on top and bottom measuring one ounce for one and two ounces for the other. With proper foresight in your investment, you can acquire a jigger with additional markings for fractional measurements. I like the Leopold Jigger but the more cone shaped Japanese Jigger is best for most users not comfortable with the metric system. I'll base the directions on this measuring system.
A Strainer. In an attempt to maintain the purity of one's libation, a strainer is a must have tool to ensure you get all of your beverage in the glass and none of the refuse obtained from the production of the drink. A quality strainer looks somewhat like a metallic paddle with slots through which liquid can flow, and a spring on the underside to aid in straining out impurities. The Hawthorne strainer made by Koriko is excellent for large mixing glasses.
A Double Old Fashioned Glass. Glassware is as important to any drink as the very ingredients within it. The old fashioned is chic and exudes a fashion forward attitude. Serving your drink in a rocks glass enhances the enjoyment by allowing the beverage to deliver its premium experience, and have room for the drink, the garnish and a large base of ice. You'll want tempered glass or crystal glasses, 12-13.5 ounces. There are countless options, but do not get a glass with a trendy shape. Just get a classic round plain glass or etched crystal.
You will not need a muddler. Muddling fruit in an old fashioned is a tradition, but it is the wrong tradition. It introduces a significant amount of juice and pulp into the drink, takes extra time and does not look as good in the glass. When you introduce juice, shaking is required, which introduces air and increases the melting of the ice. You do not want this for the perfect old fashioned. This is not a tiki drink, it is a bold, boozy, spirit first drink.
 Cocktails don't quench your thirst except perhaps psychologically. If you need hydration, use water. Always drink water with all alcoholic beverages, allowing water intake to outpace and outweigh your fermented or distilled beverages.
Next, you have to have the right ingredients. I'm not going to be able to provide you a comprehensive list of acceptable brands for your old fashioned. There are many acceptable ryes and bourbons, and some which are less desirable. Let me just put it this way, if your back hurts from grabbing your whiskey, you've bent down too far. Pick up some quality supplies. Do not spend top dollar, but do not spend bottom dollar either! Here are the items you'll need to have on the bar table.
Aromatic Bitters. There is one brand that has led the pack for generations. Angostura bitters are in the original recipe and as far as I'm concerned, they are unmatched to date. There are many options for bitters that are acceptable as a stand-in, or if you are looking for a different flavor profile, but there is not a better one. Bitters add depth, balance, spice and color to your drink.
Simple Syrup. Make this at home. Do not buy this at the store. Doing so would be lazy, and result in you paying multiple times the cost and ultimately give you a less pure product because store bought simple syrup typically has additives to make it shelf stable. To make your own, start with equal parts water and Demerara sugar (raw sugar) measured by volume. Cook it slowly in a small pot over medium heat, stirring the water and sugar together until dissolved. Let it cool and you are ready. Doing this yourself is easy, and it is worth it.
Quality Whiskey (rye or bourbon but probably rye). According to tradition, rye was often preferred over bourbon, but the drink was first invented in bourbon town and likely made with bourbon. Both are acceptable. The key is to have a flavor profile that is not too much bite, and not too sweet, most times, you'll depend on your product being aged at least four years in new oak barrels. A 90 proof whiskey (or maybe slightly higher). Usually something made with a high corn presence for a sweet buttery flavor, and rye for spice and fruit notes. My personal preference is rye. A good starting point is Bulleit Rye as a representative quality and flavor profile.
A Fresh Orange. While you're out and about, be sure to grab the freshest orange you can. This will be used for garnishing the drink, and if fresh will add flavor, aroma and enhance the presentation of the drink. Look for deep texture on the rind, and bright, glossy color. An orange without character may not introduce the character you want it to bring to your drink.
So let's get started. We're going to use the 3-3-3 recipe. This is my tried and true recipe designed to give you enough drink to satisfy you, but impress enough to leave guests eager to find out what's next. It all starts with an empty mixing glass and your bottle of bitters.
Preparing your Old Fashioned Cocktail
Three shakes of aromatic bitters. Let me tell you what not to do. (1) Don't use the big bottle, until you are more experienced. Economy sized bottles of bitters deliver more juice per shake, which may end up being too much. (2) Don't shake angry. Shaking too hard will overpower the drink and mess up your evening. (3) Don't shake scared. If you are unsure of yourself, you will produce an underdeveloped drink and shame your whole family.
Shake with confidence. Shake three times.
Three quarter ounces of simple syrup. Next up we have sugar, also known in this context as simple syrup. There is a lot of opportunity at this stage. Opportunity to impress your guests, or opportunity to wish you could switch to beer. Volume is everything here, and it's very specific.
You will be measuring your simple syrup in the one ounce side of your jigger with a 3/4 ounce mark on it. Don't measure each quarter ounce separately. Measure them all at once. When you measure, measure just under the line. That is "leave the line". Put another way, when you measure your simple syrup, I want you to get as close to the 3/4 ounce measurement mark as you can, without getting it wet. Do not measure more. If you're making two drinks in the same mixing glass, measure each drink separately.
Three ounces of whiskey. Your spirit is ready to be added. Start by measuring the first ounce in the one ounce side of the jigger. Since you've measured simple syrup, there is a trace amount left in there. I want you to use the wash of the whiskey to draw the balance of the sugar out of the jigger. Fill the jigger up to the brim, nearly if not literally overflowing. This is known as a convex fill. concave is a fill that reaches the top, but just shy of passing the brim of the jigger. Let the surface tension of the whiskey show, and then pour it directly into your mixing glass. This is important for optimal ratios and flavor profile.
As you've let the whiskey drain from the jigger, you'll see it is flipped to the two ounce side. Fill it up–convex again. You might make a little mess doing this. Don't worry about that. Grab a towel and clean up after yourself, but don't be afraid to do this right.
1x1 inch purified water ice cubes. Now that your ingredients are in the mixing glass, it's time for ice. Ice is often an overlooked ingredient. This is not wise. By volume, ice is the main ingredient in your cocktail, so skimping on quality is not advisable. What you want is clear ice when possible. At a minimum, purified water (not distilled) frozen into cubes roughly 1 inch by 1 inch squared. This is not elitist. It is important. Every bit of surface will melt and introduce water into your drink. You want this, but you want it to be right. Introducing water blends the flavors and allows it to bloom. 1 inch squared ice melts at the proper rate and meets your cooling and serving needs. You can find appropriate ice molds from Peak.
Fill the mixing glass up with ice. Fill it full, well above the height of the ingredients. The ice should heap over the liquid ingredients by about double if possible. Overfilling the container with ice is not something to be overlooked. I want the ice to be heaping.
Stir 48 revolutions. With the generous level of ice, your drink will now start to cool and dilute. The dilution adds a desirable smoothness to the drink while allowing the spirit to remain strong and provide a distinguished flavor, thanks to the hearty cubes of ice. With your weighted bar spoon, stir the ice around inside the liquid 48 times. This ensures proper dilution levels and provides you with a crisp, ice cold drink.
Prepare your double old fashioned glass. Grab your double old fashioned glass. Placing it in a fridge or freezer to frost the glass is ideal, but not necessary. Set the empty glass near your ingredients, but do not pour yet.
One big rock. Next, you will need a big ice cube. Optimal size is about 2 to 2.5 inches squared. You can get silicone ice molds for 2.25 inch ice cubes from Peak as well. Spherical ice cubes are desirable as well, as they provide the least surface area in contact with the bourbon so they last longer. This ice should be made from the same purified water that you used to make the smaller cubes, but this is where clear ice is all the more desirable. Place the purified rock in the empty glass in preparation of receiving the outpouring of the spirit.
Prepare to strain. Place your strain over the top of your mixing glass. Hold the strainer firmly, pressing forward gently.
Strain over ice. Pour the drink directly over the large ice cube. The strainer prevents any small amounts of ice from escaping the mixing glass, as your drink is poured over a fresh block of ice.
Rest. Your drink should pour to just below the depth of the ice cube, or just a little above, depending on the dimensions of your double old fashioned glass. Your drink is ready to be garnished. It's okay for it to rest and breathe while you prepare your garnish.
Swath of Orange Peel. Take your fresh orange, and peel a single swath of substantial girth from the top of the orange to the bottom. The swath of orange rind should be thin enough to manipulate, but not too thin to be firm. Hold the orange rind just over the top of your drink with the outside of the peel facing the beverage. With your fingers in both hands, pinch the peel allowing the oils within the rind to express the essence overtop of the drink. Caress the top rim of the glass with the rind to introduce some aroma on the rim and then place the rind gently into the drink vertically, with a portion of the peel exposed and a portion buried under the ice.
Done. You just made the perfect old fashioned. Please relax and enjoy.
To Cherry Debate. Although the maraschino cherry is not a part of the original tradition, it is okay to add a cherry if that is your preference, but underinvesting in cherries would be a mistake. Make sure you buy the best of the best if you're going to disrupt the perfect drink with additional fruit. The only cherries worthy of the old fashioned are the Luxardo Marchino cherries. They are not cheap, but if you wish to change the profile of your perfect old fashioned, it better be worth it.
Your drink is now complete. You're now prepared to have literally any conversation you may need to have if it doesn't require legal representation or the operation of any heavy machinery. The old fashioned is best enjoyed as an after dinner drink. Enjoy with friends or a loved one.