While it may sound a bit funny that a cocktail from the early 1900s is called the Up to Date, this Manhattan-esque classic, made with rye whiskey, Grand Marnier, and sherry, is no laughing matter.
The oldest reference I've seen for this drink is the 1916 edition of Hugo Ensslin's Recipes for Mixed Drinks. This once-forgotten collection has become one of the more famous historical cocktail books, and some claim that it was the last drink-recipe book published prior to Prohibition.
But who was Ensslin, and why should you care?
First of all, simmer down. Second, Ensslin was the head bartender at the long defunct Hotel Wallick in New York City and is credited with being the first to record recipes for a few great cocktails, including everyone's favorite bluish classic, the Aviation. The book was billed as "a complete list of the standard mixed drinks that are in use at present in New York City," and Ensslin sold copies for 50 cents. Only one problem: no one bought it.
Fast forward to the modern cocktail revival. The rediscovery of Ensslin's unpopular little book has helped drinks historians trace a number of cocktails back further than originally assumed, and even corrected an error or two. For example, the Aviation was made for decades without crème de violette because later, more popular books, like the Savoy Cocktail Book, transcribed the recipe without it. While in the future we may discover an even older source for these drinks, for now, Ensslin's book brings us more up to date in cocktail history.
Ensslin's recipe calls for equal parts rye whiskey and sherry, finished off with a couple dashes of Grand Marnier and Angostura bitters. If you're wondering how the heck to add a couple dashes of Grand Marnier to this drink, you're not alone.
A dash can be quite a variable measurement, although most folks claim it's approximately 1/8 teaspoon. I may have a heavy hand, but 2 dashes of Angostura came out to almost 1/8 of an ounce by my measurements. A fun little exercise, but so little Grand Marnier in this drink was like using none at all, thanks to the strong flavors of the sherry and rye. My advice? Keep it simple and use a quarter ounce. You'll be able to taste the sweet orange flavor and you won't drive yourself crazy trying to syphon Grand Marnier into a bitters bottle.
As for which type of sherry to use, Ensslin was of no help, just leaving it at "sherry." Sherry comes in a range of styles, and each type tastes different. I like this drink with dry Manzanilla sherry, which gives the whiskey drink a light, crisp flavor with an almost smoky presence.
If you were to use a sweeter, heavier sherry, it would be closer in flavor to a traditional Manhattan. The Angostura rounds out this classic with familiar spicy clove notes.
The Up to Date is plenty tasty, but I wanted to make something along the same lines that was a bit less Manhattan-like. This one's called Behind the Times. Think of it as the smooth-talking sexy brother of the more in-your-face classic.
Instead of sherry, the Behind the Times starts with Dolin Blanc vermouth. Instead of rich, heavy Grand Marnier, it uses Pierre Ferrand's Dry Curacao. As for the whiskey, rye was a bit too spicy for this one, so go with something Irish, like Redbreast, to make a much smoother sipper.
The drink is finished off with Dram Apothecary Hair of the Dog bitters and a lemon twist. If I were to guess, most of you probably haven't heard of Dram Apothecary, much less their Hair of the Dog bitters. These are pretty much Peychaud's bitters on steroids, with added notes of ginger, herbs, licorice, wintergreen, and citrus. If you don't have 'em and feel like MacGyvering it, substitute 3 dashes of Peychaud's and a few drops of Angostura. The results won't be quite as complex, but it'll get you in the ballpark.
The scent of this cocktail is mostly citrus, with hints of anise and sugar cane. Light and smooth on the tongue, the vermouth and Irish whisky mingle and blend, accented by herbal licorice and citrus from the bitters, while the finish is clean, fresh and crisp.