Whiskey can be a strange animal when used in cocktails. Gin is kind of the workhorse of the cocktail world; it works in pretty much everything and fails in almost nothing. But whiskey is a fickle thing. There aren’t a ton Irish whiskey cocktails, because Irish whiskey has a pretty unique profile. Cocktails made with smoky Islay whisky basically don’t exist, and the vast majority of bourbon cocktails are spirit-driven, with the exception of variations on a Whiskey Sour.

Why is that? Well, for one, bourbon kinda clashes with a lot of fruit juices. Bourbon has all of this vanilla and caramel and candied orange peel that goes well with some fruits and not others. Think about it for a minute: how many delicious bourbon drinks have you tried with lime or orange juice? One? At best? Bourbon and lime juice go together like red velvet cake and sardines, let’s just admit it.

But lemon juice? Totally. Cranberry juice? Oh, definitely. But what about grapefruit? Well, oddly enough, the most polarizing of citrus fruits is a beautiful match for bourbon, or at least it can be. You just need one more ingredient that can bridge the gap between bourbon’s sweet, earthy, caramel flavors and grapefruit’s acidic, floral tang.

Honey is this weird ingredient that can tie flavors together when you need it to. And by some miracle it sits in this perfect place between bourbon and grapefruit. Credit goes to the bartenders at Billy Wilkerson’s Vendôme Club in Los Angeles, who oddly named it for a neighboring bar, the Brown Derby. A quick search reveals the basic components go back to the Savoy Cocktail book, in a curiously similar drink titled the De Rigeur.

At any rate, the Brown Derby is one of those back pocket drinks, for the times when a guest or friend is looking for something different. And as whiskey cocktails go, this one couldn’t be much more different. And if you need a break from Mint Juleps in preparation for the Kentucky Derby, this should do the trick.

Brown Derby

• 1.5 oz Bourbon
• 1 oz grapefruit juice
• .5 oz honey syrup (1 part honey, 1 part hot water, dissolved together)

Directions

Combine ingredients with ice cubes in a cocktail shaker and shake well until cold. Strain into a chilled cocktail glass. This drink requires no garnish, though a grapefruit peel or wedge of the fruit does work well.