Jack in the Box

A tropical-influenced cocktail combining apple brandy with pineapple and bitters for a bright, fruity surprise.

The Jack in the Box first appeared in print in the Old Mr. Boston Deluxe Official Bartender's Guide, published in 1935 — the first edition of what became one of the most widely distributed home bartending manuals in American history, released just two years after the repeal of Prohibition in December 1933. Old Mr. Boston was the house brand of the Ben Ami Distillery in Boston, Massachusetts, and the guide was published both to promote their spirits and to help a generation of Americans rediscover cocktail culture after thirteen years of legal abstinence. The pairing of applejack or apple brandy with pineapple juice reflects the American distilling tradition of the time: apple brandy had been produced in New England and the mid-Atlantic colonies since the 17th century, making it one of the oldest distilled spirits with genuine American roots. Laird & Company of New Jersey, for instance, has been producing apple brandy since 1780 under a license granted during George Washington's presidency. The unexpected but logical pairing with pineapple — a tropical fruit that had become far more accessible in the canned form by the 1930s — gave the drink its playful, surprise-in-the-glass character that earned it the Jack in the Box name. The combination of domestic apple spirit with imported tropical fruit in a single glass is a small, sweet snapshot of American abundance in the post-Prohibition years.