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In most cases I didn't find much. One exception was the Alexander cocktail (and its cousin, the Brandy Alexander, originally known as the Alexander II). There are many theories about where the Alexander originated, but the most popular is that it was created in the early 20th century in New York by a bartender named Troy Alexander to celebrate the fictional Phoebe Snow. The Delaware, Lackawanna and Western Railroad had launched an ad campaign to promote its use of clean-burning coal that featured Snow (a cartoon character) wearing all white, so Alexander created a white cocktail: equal parts gin, cream, and white creme de cacao. (Another theory is that it was created in honor of the baseball player Grover Cleveland Alexander during the 1915 World Series.)
At some point, brandy was substituted for gin, creating the Brandy Alexander—which gradually became more popular than the original version. Tasting the two, it's easy to see why: the smooth, caramelly flavors of brandy go much better with cream and chocolate than gin does. Historically gin was sweeter and less herbal in flavor than most are these days, which might lend itself better to this cocktail. What I had on hand, however, was Tanqueray. I followed the traditional 1:1:1 proportions, and created a cocktail that didn't taste like it was meant to exist. Each layer asserted itself independently—gin, then cream, then a little chocolate—refusing to meld together. The chocolate was barely there, but still didn't go with the grassy gin.
The Brandy Alexander, on the other hand, fared much better in my tests (even though I only had cheap brandy). I used both of the creme de cacaos I'd made—one with an 80-proof vodka base, one with a 151-proof rum base—to see which worked better. The cocktail with vodka was creamy and chocolatey, much like chocolate milk. It's perfectly pleasant and not too sweet—but after I tried the version made with the rum, it tasted like a kid's drink. The rum-based creme de cacao created a more complex flavor with deeper chocolate tones and roasty, slightly bitter finish.
I'd have to taste the drink to figure out what proportions would work for my particular creme de cacao, so I started with relatively small amounts: a half ounce of lemon juice, three-quarters of an ounce each of creme de cacao (I used the rum-based version) and bourbon, and a half teaspoon of grenadine. That turned out to be mouth-puckeringly sour, so I upped the grenadine to a teaspoon and a half (a quarter ounce) and doubled the bourbon to an ounce and a half. The adjustments helped things, but I couldn't taste the chocolate enough, so I added another quarter ounce of creme de cacao. The result was a fairly tart cocktail—you can taste the lemon and pomegranate at the beginning, followed by chocolate, which creates a roasty, almost smoky finish (similar to the Brandy Alexander). I realize that doesn't sound like a promising combination, but the bourbon manages to both slip into the background and also tie things together. Imagine a whiskey sour, and then a bourbon drink with dark chocolate flavors. Marrying the two might not seem like a natural fit, but it does create a pretty interesting cocktail. Adding a little more sugar probably wouldn't hurt anything, but I liked its tartness.
Commodore (modified version)
.5 oz lemon
1 oz creme de cacao
1.5 ounces bourbon
.25 ounces grenadine (or more, to taste)