This drink is widely reported to be first printed in “Recipes for Mixed Drinks by Hugo Ensslin in 1914”. This is completely inaccurate for several reasons. First, it was not even listed by name or ingredients and second, The book was not in stores until 1917 as seen here:
Catalog of Copyright Entries. Part 1. [A] Group 1. Books. New Series – Page 427 by Library of Congress. Copyright Office in 1917
“(17-15057) 2618 Ensslin, Hugo R. Recipes for mixed drinks, by Hugo R. Ensslin. [2d ed.] [New York, Fox printing house, … HR Ensslin”
This doesn’t mean the drink itself was not in circulation as the time, it very likely was. This story behind this drink probably was originally purported by someone who had done research on the drink, but could not determine an answer so they took an educated guess. This drink actually appears as early as:
Anthony Trent, master criminal – Page 245 by Wyndham Martyn in 1918
“Monmouth was a careful soul for all his gentle languors and sauntered into the tap room and demanded an Alexander cocktail. As became a son of Wisconsin, Oscar was free and friendly.”
It is undetermined where this drink originated, however, there is overwhelming evidence it was named after the popular song “Alexander’s Ragtime Band” which was covered literally hundreds of times from 1910 – today and was even followed by a 1938 film by the same name.
Given the style of music, this certainly would have been a favorite in speakeasies around the nation. This drink is indirectly responsible for the Black Russians confusion of contents. This is also exactly why the Brandy Alexander is made with dark creme de cacao and the Alexander is made from clear creme de cacao.
Some point after Kahlua claimed the Black Russian, Bartenders certainly would have been confused as to the ingredients of an Alexander. So the dark vs clear creme de cacao difference between the Alexander and Brandy Alexander was caused by Kahlua directly. But this is only speculative and there is little in the way literature support this claim.
Nonetheless, the is a wonderful drink and is still popular today. This drink dates between 1910 – 1912 and contained at least as of then:
Shake these ingredients with cracked ice, though normally you would “roll” these ingredients:
Gin (Old Tom Gin is printed as early as 1930)
Clear Creme de Cacao (Dekuyper is used as early as 1938)
Strain into a chilled cocktail glass, add fresh grated nutmeg garnish