Whiskey Cocktail Hour: An American, A Spaniard, and A Frenchman Walk Into A Bar

The weather is cooler and rainy this week in Portland, so I’ve turned to more spirit-forward cocktails. Stirred & boozy is often my cocktail style of choice in the fall and winter, mostly because the thought of drinking an iced cocktail is unappealing when I’m wearing as many layers as possible to keep from freezing my butt off outside.

There are a few classic cocktails that come to mind when I think of stirred whiskey drinks. The Sazerac and the Manhattan are the ones that I think of immediately. Chances are you probably had a Manhattan before you discovered the joys of the Sazerac. The Manhattan is great drink that, sadly, can easily go astray with the wrong combination of whiskey and sweet ermouth, or just as easily by the wrong ratio of whiskey to vermouth.

This cocktail is a variation on the Up to Date cocktail from Hugo Ennslin’s book, Recipe’s for Mixed Drinks, which itself appears to be a variation on the Manhattan. Ennslin’s recipe calls for equal parts Rye and Sherry, and a couple dashes of Grand Marnier and Angostura Bitters. Sounds pretty delicious, right?

I enjoy Grand Marnier, but it is quite sweet and I tend not to use it in a cocktail unless I really want to add a rounder, fuller mouth feel. That round, sweetness tends to be the reason some people opt for it in Margaritas instead of Cointreau or standard Triple Sec. It just mellows out those really sharp, sour notes. Which sometimes can be a good thing, but for this drink, I wanted to keep things on the lighter side.

Instead of the Grand Marnier, I subbed in Cointreau as my orange liqueur of choice. Cointreau is quite a bit drier and lends a bright, crisp orange flavor to a drink. Not wanting to sacrifice mouthfeel though, I opted for an oloroso sherry to keep a bit of roundness in there, but scaled the ratio back slightly. I also used vanilla-infused bourbon for my base spirit in place of the rye. The vanilla added an extra layer of complexity, and was a nice compliment to the orange flavors. I doubled down on the orange by using orange bitters instead of Angostura. The finished product needed a little something extra, so I garnished it with star anise, and that seemed to tie all the components together.

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I think this is a really enjoyable drink, and an easy one to stir up at home. Let me know what you think if you decide to tinker around with it. Cheers!

An American, A Spaniard, and A Frenchman Walk Into A Bar

1 1/2 oz vanilla-infused bourbon*

1 oz oloroso sherry

1/2 oz Cointreau

5-6 drops Regan’s Orange Bitters

Star anise for garnish

Instructions: Add all ingredients to a mixing glass, add ice, and stir for 30 seconds. Strain into a chilled coup and garnish with a piece of star anise.

Vanilla Infused Bourbon

*Vanilla-Infused Bourbon (aka Vanilla Extract)

1/2 cup Bourbon

Mexican Vanilla Beans

Instructions: Using a knife, split the beans down the middle to expose the seeds on the inside. Cut the beans in half, along the equator, and add them to a mason jar. Pour the bourbon over top, and seal the jar. Allow to rest for 6 weeks, shaking every few days.  Side Note: The longer you leave the beans in the mixture, the more the flavor will develop. Beans that have been left for a year or more make for the best infusion. I use this stuff in my coffee and in baked goods. It’s delicious! If you want a more pure vanilla taste for baking or making desserts, just use vodka instead of the bourbon.

For more recipes like this, check out fern + shaker and follow @fernandshaker on Instagram.

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Emily Ross-Johnson

Emily is a bit of a Jane of All Trades. She started her career as an opera singer in NYC, and over time gravitated to the Food & Beverage Industry. Over the span of her professional life she has performed at Carnegie Hall, founded her own Whiskey Society, represented numerous...