Darkside

This smooth sipper from Adam Bernbach of Proof in Washington, DC has undertones of cherry and anise.

Italian Buck (Amaro and Ginger Beer Highball)

This fizzy, spicy, sweet-tart, and bitter drink was created by Jamie Boudreau of Canon in Seattle, and appears in Amaro by Brad Thomas Parsons. It's a little like a bitter, gutsy take on a Dark 'n Stormy, but instead of rum, the drink is made with two bittersweet Italian liqueurs: orangey Montenegro and vegetal Cynar.

Mela d'Alba (Apple Brandy Negroni)

This apple brandy–based variation on the classic Negroni cocktail is spicy, rich, and bittersweet.

Blonde Redhead

This cocktail, created by Douglas Derrick of Ava Gene's in Portland, Oregon, is a masterful combination of just three ingredients: spicy whiskey, luscious vermouth, and complex Barolo Chinato, a bittersweet, herb- and spice-dosed digestivo made from one of Italy's best wines. The result is chocolaty, smooth, and deep. Though it's in the same family, it's subtler than a Boulevardier.

Architects and Kings

Bartender Josh Relkin developed this recipe for Sable Kitchen & Bar in Chicago. It plays on the bitter side of coffee, adding herbal amaro and spicy bitters. Topped with whipped cream, it's a great way to wind down after dinner.

Dutch Alps

This variation on the classic Irish Cocktail uses genever instead of Irish whiskey, and herbal genepy instead of absinthe. Rather than sweetening with orange curaçao, this one calls for rich, citrusy Amaro Nonino.

Aviary's Bitter

The Bitter cocktail, from the Aviary in Chicago, is served in a glass that's been smoked over a piece of smoldering bourbon barrel stave, which is custom-cut by the cocktail lounge's industrial designer. Fear not—we love this cocktail with or without the touch of smokiness! But if you're feeling adventurous and want to truly re-create this drink at home, used small-format, seasoned barrels are available for purchase online from New York's Tuthilltown Spirits, makers of Hudson whiskey.

Basin Street Blues

This cocktail, adapted from Domenica in New Orleans, is pretty low in alcohol, but not at all low in flavor. It reminds us of caramel and lemon drops, with an essential smoky addition from a few drops of Scotch.

Blood Orange Negroni from Bottega

This Negroni variation from Chef Frank Stitt appears on the menu at Bottega only in deep winter when blood oranges are in season. "It makes us reminisce about aperitif time in the gorgeous cafes and bars of Torino and Venice," says Stitt. Serve with a slice of orange and a bowl of green olives.

Bellissimo Aceto (Lambrusco-Amaro Cocktail)

The garnet color of this sparkling Lambrusco-based cocktail, from Corey Phillips of Bellina Alimentari in Atlanta, makes it feel festive. But the real reason to serve it this winter is that the bittersweet, tart, and fruity flavor is perfect with rich cocktail-party fare.