Ingredients: Bourbon or rye whiskey, sweet vermouth, bitters
Backstory: We presume the cocktail was first poured in Manhattan, but whether that was at the snooty Manhattan Club in the 1870s or in other locales on the isle in the years beforehand has yet to be determined. The drink has always had sweet vermouth, bitters, and whiskey, but over the years that latter ingredient has jumped around between bourbon, rye, and even Canadian Club. As rye made its triumphant return in the last decade, it has come to rule the roost. And new variants of the easily-made, 2:1 cocktail have also emerged, many with Brooklyn neighborhood names like the Red Hook and Bensonhurst.
Why it’s a classic: “A Manhattan brings the spiciness of rye whiskey balanced by the sweetness of fortified wine vermouth. This is a great entry level cocktail for the person just discovering American whiskey, yet still a joy for the more developed cocktail consumer.”—Laboy
2 oz rye whiskey 1 oz sweet vermouth 2 dashes Angostura bitters
Stir the ingredients with cracked ice, then strain into in a chilled coupe. Garnish with an orange twist or brandied cherry (none of that cheap maraschino bullshit).