Where can one find greater enchantment than in the poised simplicity of the archetypal Old Fashioned cocktail? A historic concoction of whiskey, sugar, and bitters, ornamented with a twist of orange, this libation has been captivating drinkers since the 19th century.

A cocktail whose popularity has proven to be enduring, the Old Fashioned is simply a blend of spirits, sugar, bitters, and water. Over the years, as various versions of this cocktail blueprint began to materialize, fans would often request their mix in the “Old Fashioned” style - and the name caught on.

“Old Fashioneds have demonstrated their longevity for a solid reason,” observes Resa Mueller, the general manager at Philadelphia’s R&D Cocktail Bar. She asserts, “These cocktails are sufficiently straightforward and accessible for the most novice home bartender, yet, they are complex enough under the expertise of a skilled bartender to feature a truly exquisite whiskey.”

Presently, the Old Fashioned primarily employs American whiskey, but traditionally, it could be crafted with a variety of spirits. Lindsay Matteson, the beverage director and general manager at Hell or High Water in Louisville expounds, “You could order a Whiskey Cocktail, a Gin Cocktail, and so on. The minor addition of water and bitters would dissolve the sugar cube. The use of fruit seems to have been during Prohibition to conceal inferior quality spirits.”

Indeed, the modern Old Fashioned would likely be served with a large ice block and exquisitely garnished with a slim slice of orange peel. “Given that it only involves four ingredients, the whiskey selection will drastically influence the flavor of the drink,” advises Matteson.

Choosing the right bourbon for an Old Fashioned requires careful deliberation. Matteson continues, “When opting for a bourbon for an Old Fashioned, balance is crucial. Depending on your taste buds, you may prefer something bright with orange flavors, or dryer variants with black pepper notes.”

A similar belief is held by Mueller, who asserts, “Consideration for the balance of flavor is also vital. I generally prefer bourbons with a more robust proof and a dominant flavor profile that corresponds well with other ingredients in the cocktail.”

Today, there is a myriad of quality bourbon options on the market. To aid in the selection process, we observed a few of their preferred bourbons used by bartenders across the country when crafting an Old Fashioned.

Elijah Craig, an individual allegedly the first to commercially distill whiskey in Kentucky, lends his namesake to one of the finest modern Kentucky Straight Bourbons. Matteson shares, “Elijah Craig consistently cultivates a decent Old Fashioned. Remarkable proof with an excellent body, it fuses grassy notes with bright citrus flavors, producing something remarkably complex for the price.”

Less acclaimed, but no less impressive, Old Grand Dad Bottled in Bond has gained a cult following from connoisseurs and bartenders alike. It offers value for money with noticeable flavor notes of butterscotch, caramel, and baking spice.

On the other hand, there's Few Straight Bourbon, a relative newcomer from the Chicago area. Mueller says, “Few Straight Bourbon is one of my preferred whiskeys for a classic Old Fashioned. It has a high-rye character that takes center stage, and its beautiful spice level makes you crave more.”

Another noteworthy bourbon is the Widow Jane, crafted in Brooklyn and is perfectly suited to bolster an Old Fashioned cocktail. Matteson extols, “The proof brings out more spice in the whiskey that compliments the bitters in an Old Fashioned perfectly, and there are great dried fruit notes for added complexity.”

Rounding out the exceptional list of bourbons is Maker’s Mark, possibly the most recognizable bourbon on the market. “Maker's Mark is my choice for a dessert Old Fashioned, it's hard not to love,” confides Matteson.

For some, no list would be complete without a mention of the famed Buffalo Trace distillery. Based in Frankfort, Kentucky, Eagle Rare is a crowd favorite. When stirred with sugar and bitters in an Old Fashioned, the decade spent maturing in oak gives the bourbon a rich, toasty character with just a hint of wood tannin.

The old adage stands true: the perfect whiskey creates the perfect Old Fashioned. Here's a toast to timeless classics and trusty favourites.