When did the Old Fashioned become old fashioned? It's not an easy question to answer: the first mention of the cocktail as 'old' occurs around 1880 in a bar called the Pendennis Club in Louisville, Kentucky, suggesting that the basic formula -- bourbon, some sugar, a dash or three of bitters, a twist -- might have been around well before that. In fact it seems plausible that the drink was around for the inception of the cocktail, making the drink itself not just old, it's positively primordial, cocktail-wise.
Like many other early life forms, its simplicity is one of its greatest virtues: the combination of spirit, sugar and bitter fit together with the natural symmetry of a golden mean: The bite and backbone of bourbon ameliorated by a dash of sugar, given depth and fortitude by a dash or two of bitters, makes for a drink so cozy and yet so poised it seems close to perfect. So perfect, in fact, that it's one of the seven classic drinks cited in David Embury's classic 1948 book, The Fine Art of Mixing Drinks.
As such it hardly seems like a cocktail to sully. Use a high-quality bourbon like Bulleit, Four Roses or Buffalo Trace. If you're feeling randy you may wish to substitute brandy, as they do in my home state of Wisconsin and almost nowhere else.
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You may also wish to find something slightly less simple than simple syrup. A worthy substitute is Madeira, a rich Boal or Malmsey Rainwater, which adds maple or molasses notes and comes in a bit drier than sugar (with Grenadine, this would be another near-classic, the "Take the A Train.") Sherry, too, can be employed for the sweet component, though only if it's a cream sherry.
And since we live in a world of endless bitters possibilities, experimenting with the back end seems like a very good idea -- the sour cherry from local producer Miracle Mile, for example, might give off just enough subtle fruit, or consider either of Anderman's citrus flavors, yuzu and orange, which would brighten the topnote delicately. But don't digress too much -- messing with perfection can disrupt the chi of a perfectly good drink, one with the proper warmth for a cool fall evening.