As I explored various cocktails over time, I eventually reached a point where I realized I probably needed a bottle of whiskey for some of the recipes. I knew very little about whiskey, but assumed a Whiskey Sour would be something worth trying. So in the fall of 2015 I took a ride over to a large, liquor store not far from me (my first mistake) and asked for recommendations. They suggested a bourbon they said would be good for beginners, and I headed home, eager to try my first whiskey cocktail.
Still learning, I figured a simple Old Fashioned would be a good place to start. It seemed like an easy enough recipe from my basic bar book. That turned out to be mistake number two. I had no idea at the time that a sugar cube was a standard unit of measure, nor that a single Domino sugar cube was actually half the expected portion. I also had no real clue what a “dash” of bitters meant, and naively assumed it was equivalent to a single drop. So I basically had made myself a glass of whiskey, with only half the sugar and just three drops of Angostura. I followed the book’s dated instructions to add a few drops of water and muddle the bitters and sugar before adding the bourbon. At this point, there were too many mistakes to count.
As you can probably guess, this was not a great bourbon, not a good first whiskey, and definitely not a good choice for a first impression. The result was very far from stellar. The first sip was unpleasant; the second didn’t improve things. Inspired by probably every Western with a bar scene, I also poured myself a shot to try it neat. A warm shot of bad bourbon did nothing to redeem the experience. My wife summed it up best after one sip of my failed Old Fashioned: “Uck. Only an alcoholic would like that.”
The bottle went on a shelf, out of mind unless I needed whiskey for a recipe, which I assumed would be rare or perhaps… never. At that point, I was sure I didn’t like whiskey.
A few months later, though, in late January, my wife told me about a great cocktail she’d had at lunch with a friend at one of our favorite spots in Stony Brook, Pentimento (long gone now but always remembered). It was called a Brown Derby. When I looked it up, I was surprised to see it was whiskey-based, but I figured some of them must be good. Just a couple of days later, we were out to dinner at Plan B Burger in Springfield on our way up to Vermont and noticed a surprisingly similar drink on the menu: a Gold Rush. We ordered it and enjoyed this equally awesome cocktail.
It was an eye-opening moment: we actually liked bourbon. We just hadn’t had the right introduction.
While that bad introduction had convinced me I didn’t like whiskey, understanding how well-balanced a cocktail could be with it literally changed everything. I started seeking out other whiskey cocktails, learning how it worked with a wide range of liqueurs and ingredients, and perfecting how to make great drinks with it. As you can imagine, I’ve learned what makes a fantastic Old Fashioned, as well as some exceptional modern variations. I also began exploring better bottles, learning the differences between bourbons and ryes, as well as Scotch, Irish whiskey and a few others. Along the way, I added plenty of whiskey-based drinks to my regular rotation while building a collection that spans everything from reliable everyday bottles to some harder-to-find gems. Over time, I came to appreciate the complexity and depth whiskey offers, and today, it’s my favorite spirit, whether I’m enjoying it on its own or in a cocktail like a well-made Manhattan, one of my favorites.
Looking back, that terrible first Old Fashioned wasn’t a failure; it was just the first step in learning what good whiskey could really be.
