The Old Fashioned is whiskey, sugar and bitters, and somehow that's enough. If it's your drink, these are the ones to try next, each with a note on what it shares with the original.
The Manhattan (also has bourbon and Angostura bitters); the Mint Julep (also has bourbon and simple syrup); the Sazerac (also has bourbon and simple syrup); the Flying Scotchman (also has Angostura bitters and simple syrup).
How are these drinks picked?
From the recipes, not by hand: drinks that share at least two ingredients (sugar aside) with the Old Fashioned come first, then ones with the same base spirit, a similar flavor profile, the same kind of drink and the same method.
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