The first week in May is always a dilemma in the making here at Drink of the Week Plaza as it actually pits two of the year’s biggest drinking excuses holidays against each other. Since tomorrow is Derby Day and Cinco de Mayo is in the middle of next week, I’m going to start with that and follow it up with a belated Mexican-themed cocktail for next week. Not ideal, I know. It is, of course, entirely coincidental that mysterious forces bribed gifted me with a free bottle of Wild Turkey 101 Straight Bourbon and this week’s intriguing, imaginative variation on a traditional Mint Julep.

Though I still have a spot soft for good Old Fitzgerald when you can find it, I have to admit that this expression of one of the best known names in American whiskey is about as good a high-proof bourbon as you’re likely to get for under $20.00 for a fifth. It offers a very nice balance of sweet and tough flavors that have made for plenty of good reviews and a number of good cocktails.

Which brings us to this week’s variation on the ultimate Derby Day classic. It pairs the bourbon with, of all things, an artichoke-derived amaro-style liqueur beloved of the cocktail cognoscenti. Can these two crazy ingredients have a shot at a long and happy life together? Let’s find out.

The Grandstand Julep

1 1/2 ounces Cynar
3/4 ounce Wild Turkey 101 Bourbon
1/2 ounce simple syrup
1/2 ounce fresh lemon juice
1/2 ounce fresh grapefruit juice
12 mint leaves
2 ounces soda water
2 dashes Fee Brother’s Grapefruit Bitters

Build this one in a julep cup if you’ve got one and a good size rocks glass if you don’t. (I don’t!) Combine the Cynar, Wild Turkey, juice, mint leaves (given the differing sizes of mint leaves, the number is an approximation at best), and simple syrup…you can also substitute two and half teaspoons of superfine sugar if that’s easier. Gently muddle the leaves in the liquid.

Next, add crushed ice, follow with the soda water and then top the whole thing off with the grapefruit bitters. Start to sip slowly and toast our equine friends. Alternatively, you can toast W.C. Fields, who is supposed to have said that horse sense is what keeps horses from betting on people.

*****

While you could theoretically try this drink with another bourbon (it better be a strong one), there isn’t much room for messing around with the main ingredients here. Mainly that’s because there’s only one one type of Cynar available and it’s made by the manufacturers of Campari.

The exception is actually your ice, which really does need to be crushed. I’m lazy and tried this drink several times with ordinary ice and found it tasty and relatively well balanced but bordering on cloying. Crushing the ice, while admittedly a bit of a hassle, opened the drink up and took the edge off the very sweet/very bitter flavors. My only other advice is not to drink this one too fast. You want to let that crushed ice melt a bit. Take your time with this one and leave the racing to the horsies.