The Red Hook

Here's a relative of the Manhattan that dates to within the past five years, a drink created by New York bartender Enzo Errico that utilizes its ancestor's rye whiskey base, matches it with the bitter Italian vermouth Punt e Mes, and fills in the flavor with a hearty dose of funky maraschino liqueur. Named for a once rough-and-tumble Brooklyn neighborhood that's since changed with the times, the Red Hook is one of the more memorable variations of the Manhattan.

The Brooklyn Cocktail

A spirited riff on the better-known Manhattan.

The Claridge

But while the Slope keeps me coming back to the magical interaction between rye whiskey, apricot brandy, and bitter vermouth, the Claridge keeps the stone fruit's appeal alive when it's mixed with gin and dry vermouth.

Manhattan Cocktail

The stiff, smooth union of whiskey and vermouth is a classic of the cocktail canon.

Man About Town

This cocktail from Gramercy Tavern in NYC is a take on a Boulevardier (which is like a Negroni, but with bourbon instead of gin). Here, however, spicy rye is the star, complemented by the bittersweet Sicilian amaro, Cynar.

Manhattan Cocktails (for a Crowd)

Batch up a bottle of Manhattans for your next party!

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.

The Bronx

Let's be honest: The Bronx is unlikely to be anyone's favorite drink. But while it's not exactly bottled excitement, The Bronx is actually pretty good, and surprisingly refreshing. Be sure to use fresh-squeezed orange juice (and if you add a dash or two of Angostura bitters, you've got a somewhat tastier Income Tax Cocktail on your hands), and approach it with an open mind.

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.

The White Manhattan

The White Manhattan takes one of the 19th century models of a Manhattan—whiskey, vermouth, bitters, and a trace of liqueur just because—and tweaks it to accommodate the bright, malty flavor of unaged white dog whiskey.