The Derby

At least three different cocktails bear the name Derby, to commemorate the long bond between drinking and betting on horses.

Irish Cocktail

This classic drink is similar to the Improved Holland Gin Cocktail, but uses Irish whiskey instead of malty genever.

The Bitter Irishman

This St. Patrick's Day-appropriate cocktail is way better than green beer. The whiskey is light and almost floral, and the amaro is spicy and rich. Fresh lemon gives the drink a punch of refreshing sour flavor, and the drink finishes up with the whiskey's bite and a little bitterness from the amaro.

The Emerald

There are pitifully few decent cocktails mixed with Irish whiskey—like scotch, it just doesn't play well with other ingredients—but here's one that's not only suitable for the day, but absolutely enjoyable: the Emerald.

EVR's Whiskey Sour

Two whiskeys (Irish and single-malt Scotch) come together in this rich, leathery-textured sour from Orson Salicetti of EVR in New York.

Irish Coffee

Hold the Bailey's, and don't overdo the cream or sugar.

The Devereaux

We've always liked sparkling wine with a splash of elderflower liqueur, but this highball from Freemans restaurant in NYC raises the bar a bit with the addition of Bulleit bourbon and some tart lemon to even it out.

Diablo

Really, who'd think that the zippy New-World spirit from the agave would match so well with a demure liqueur flavored with an Old-World fruit? But there's just some kind of romance between the two that defies explanation; all you need to know is that separately, they can be very entertaining, but together, they're dynamite.

Irish Coffee Caramel Ice Cream with Shaved Dark Chocolate and Candied Pecans

It has buttery, smoky caramel, a dash of coffee grinds, and a generous helping of whisky for good measure. It's a bracing combination, but oh does it work. First you taste the coffee, roasted and rich, with the pleasant bitterness of an actual cup of joe. Then comes the caramel to sweeten things up just a tad, melting to sweet buttery goodness. Then the whisky: the more ice cream you eat, the more you taste it.

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.