I think this is my favorite drink. It’s one that can also tell people a lot about how you like your cocktails. That sounds pretentious, but it is what it is. I also feel that you can judge the quality of a beverage program based on how a bartender puts together one of these classics. I shit you not there is a “high end” steak house that served my friend an old fashioned made with crushed ice and Splenda. After that I ordered a Miller Lite.
I was hesitant to even write this recipe because everyone seems to enjoy their Old Fashioned differently. I find that people who really enjoy bourbon, enough to enjoy it neat, will desire an Old Fashioned that is barely sweet with just a hint of bitters, topped with a cherry and orange peel. At the end of the day they want to taste the bourbon. Others will gravitate to something a bit more sweet, maybe a bit more disguised with bitters that takes the edge off the bourbon flavor. There isn't a right answer here.
There are wrong answers though. At least in my opinion. There are two areas that I am adamant about when talking about Old Fashioneds; Big Ice and Stirring.
Ice: The ice you use here should be in large chunks. Avoid crushed ice like the plague. You want to be able to control the dilution of the drink. Introducing water is critical, but the smaller the pieces of ice used, the less control you will have as you prepare and later drink the cocktail. Which leads me to…
Mixing: A good old fashioned should be stirred. Shaking just muddies up the cocktail, brings in little chunks of ice, and makes it foggy. Frankly, I hate it. There are people who say it needs to be stirred for at least 60 seconds but those are the same people who say you aren’t a man if you flip a steak more than once, take them with a grain of salt. I’ll drink my Old Fashioned while watching you try to come up with excuses to explain away your shitty, unevenly-cooked steak to your drunk neighbor at the block party. Ignore these “rules” and figure out what gets you to the flavor you want with the ice you use. I find it to usually be between 15-30 seconds before it gets to the point I like.
This is a bourbon forward drink, so you will want to go with a middle of the road to good-bang-for-the-buck bourbon. I like to use an Old Forester, Bullet (or Bullet Rye), or 1792.
2 Oz Bourbon
.5 Oz 2:1 Simple Syrup
3 Dashes Orange Bitters
2 Dashes Aromatic Bitters
Maraschino Cherry (Luxardo when possible)
Step 1 - Set up a rocks glass with a large piece of ice
Step 2 - Set up a Cocktail mixing glass with enough ice to get about ⅓ of the way full.
Step 3 - Add bourbon, simple syrup, and bitters to the mixing glass
Step 4 - Mix for at least 15 seconds. Give it a quick try with a straw, and repeat until you figure out the timing for yourself
Step 5 - Strain over fresh ice into the rocks glass
Step 6 - Garnish by twisting the orange peel over the top of the glass to release it’s oils, and drop a cherry on a toothpick into the drink
Old Fashioned Advice
Look, at the end of the day, this is a highly personal drink. The good news is that there ain't that many ingredients to experiment with balancing. Don't be afraid to give different bitters a shot either, there are some really cool craft ones out there.