The way I see it, like first loves, pizza, and doctors, your first Old Fashioned probably goes a long way toward defining what the drink is to you. For me that means a not-too-sweet bourbon, a muddled maraschino cherry, a dash of Angostura, and an orange twist swiped around the inside of the glass.
Though I'm really more of a gin guy, and I prefer my bourbon neat, this is a cocktail I'll turn to whenever I want to feel like a civilized grownup. I love how the force of the booze is set off by the delicate sweet-bitterness of citrus skin and the warm spice of the bitters. It eventually hit me that if this combination tastes so good in a cocktail glass, there's no reason it can't be similarly awesome in an ice cream.
This recipe is even easier than your standard vanilla bean, and it preserves all the intensity and surprising delicacy of a real Old Fashioned. If anything, the dilution of all that cream allows the burnt caramel and bitter-sweet citrus flavor of the drink to come through all the more clearly.
To complete the Old Fashioned effect, top your scoop with a couple maraschino cherries, preferably the expensive but oh so delicious Luxardo kind. Other candied sour cherries, like these little Greek guys, also work quite well—frankly they're my budget-minded go-to cocktail standard.
How do you take your Old Fashioned? And what other classic cocktails do you want to see in ice cream form?