Rule 37: Jack-In-The-Box Cocktail


Modern Drunkard Magazine’s articleThe 86 Rules of Boozing, by Frank Kelly Rich states:
Rule 37. Try one new drink each week.
The Rule 37 series of posts chronicle my attempts to accomplish this feat every week.
For the recipes of R37s past, click the Htf do I make these drinks? tab.



I just wanted something tasty.
That’s all.
Minimal effort.
You know, one of those Friday evenings when you don’t want to think/blog too hard.
Oh, you don’t have a blog?
I do, and sometimes it’s a pain royale with cheese. Until I have a drink or two. Then it’s easy.

The usual Friday night routine involves finding/choosing a unique Rule 37 drink because I haven’t bothered to do that step in the preceding week. Usually. Sometimes I do, and that makes everything easier. When I have a starting place, it helps a lot. Once the drink has been chosen, I have to think of the “hero,” or main shot of the cocktail itself because I haven’t bothered to do that step either. This means choosing the right glass, deciding on a lighting setup, choosing a background, testing the lighting setup, deciding it doesn’t work, redoing a different lighting setup, chilling the glass, making the drink, making the garnish, getting the chilled glass out of the freezer, pouring the drink and staging the garnish all before the foam/oil on the drink surface dissipates and the frost on the glass melts. Before I even get to taste it.

First world problems. I am aware of this.


In hopes of finding something simple, I started flipping through a 1965 edition of Mr. Boston and found some wacky stuff, but this one didn’t seem too outrageous. Just equal parts apple brandy and pineapple juice, with a dash of bitters. I’ll give it a try.

There doesn’t seem to be much history or story behind this one, though many examples of the drink appear throughout Teh Interwebz, though one is a completely different concoction using vodka. Ick.


rule37jackintheboxJack-in-the-Box Cocktail
From Old Mr. Boston De Luxe Official Bartender’s Guide, 1965 ed.

– 1 oz apple brandy (Laird’s)
– 1 oz pineapple juice
– Dash of bitters (Angostura)

Old Mr. Boston sez “Shake well with cracked ice and strain into 3oz cocktail glass.”
Simple enough. Shake it VERY well to get a nice foamy pineapple juice, and serve it in a chilled glass. I made a double, which fit quite nicely into a modern 5oz cocktail glass.



Yup. Pretty easy. I don’t have any FRESH pineapple juice on hand at the moment, so the canned will sadly have to suffice for tonight. One review stressed using the fresh juice, and normally I agree, but I don’t have a method of juicing fresh pineapple. Yet. Citrus fruits, yes; large tropical hard fruits, not so much. The drink turned a lovely orange-pink color, but it looks lonely without a garnish.

rule37jackintheboxbottlesIn we go. Well. It smells of apples and the so-called pined apples. They kind of battle back and forth between tart and sweet, with the crisp apple seeming almost sour up against the syrupy tropical nectar. There’s an astringency in there as well (the Laird’s Straight Apple Brandy is 100 proof) which is likely providing some of the sourness, and deep underneath lurks the cinnamon spice of the Angostura. I suspect that the drink needed a heftier dose of bitters, but we’ll see when I sample it.

There’s also a waft of mildew from the Old Mr. Boston. Old indeed.

Sour start. It’s the apple tart combined with the alcohol that begins the drink with a frowny note. The pineapple washes in to cheer everything up, all sugar and sunshine, then a kick of booze stings the tongue pushing the pineapple aside. The Angostura comes in on the heels of the alcohol fire with a dry spice linger in both the flavor and mouthfeel. It finishes a tad sour and dry overall. Sometimes that apple brandy lends a sweetness, and sometimes a tart sour depending on the other ingredients.It plays the part well, lending that alcohol pucker when you need it, or an apple crisp sweetness when up against bitter foes, like Chartreuse.


rule37jackintheboxaltIt’s by no means bad, but just not as fruity and sweet as I would have expected. Quite well balanced, actually, as pineapple just can be TOO sweet if you let it. The Angostura really did come through in the flavor, and the play of apple and pineapple wound up being more interesting than anticipated. You could make a milder, sweeter version of this using the regular 80-proof Applejack, but I think the added boozage helps tame the tropical sweetness to a good balance. I’m dying to try this with FRESH juice and reevaluate. Perhaps soon.


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One thought on “Rule 37: Jack-In-The-Box Cocktail

  • MikeQ

    I remember Johnny La La showing me how to make a “Jack Rose” with Laird’s back at The Lark Tavern (Albany, NY.) With all the drinks you’re making, you must have a well-stocked bar … don’t suppose you’d invite me over sometime? (Only kidding, I remember you refused to let me borrow that killer car of yours.) Good post, as always. This site is a great resource … also a fun read.