Tread gently into this particular corner of the cocktailian past. The antiquity of applejack ensures that some drinks mixed with it are perfectly antiquated. Take scotchem, which, as described in an old tavern tale, is made with applejack, hot water, and "a good dash of ground mustard." I endeavored to try one of these in sympathetic circumstances, on the evening of an unseasonably early snowfall. There was meanness in the wind and moisture in my socks as I bolted home from the store with a box of Colman's. Drinking my scotchem, I felt as if I'd curried my own thorax. There is little need of it in a century blessed by central heating, polar fleece, and microwave soup bowls.
Tread gently. Stay flexible. The origins of very many classic cocktails are matters of frantic dispute. There are perhaps a dozen stories about the invention of the margarita, most having to do with the barkeep's attempts to honor and/or hump a woman named Margarita or Margaret or Marjorie. But applejack cocktails tend to have especially murky histories.
For instance, opinions are divided on whether the stone fence—a spiked cider currently popular in the White House—earned its name because it will inspire you to try vaulting one or to believe that you have barreled downhill into the same. An old issue of the trade magazine American Bottler confuses the issue further by suggesting (in antique orthography) that "once properly prepared, [the drink's] hardness is only paralleled by a pile of granite bowlders."
For instance, the conjunction of applejack and sweet vermouth is sometimes known as an Applejack Manhattan and sometimes as an applejack cocktail and sometimes as a Jersey lightning or a Marconi wireless or a star cocktail, depending on who's doing the knowing and his sense of proportion. (This is one of those occasions where pretending to know will likely suffice. As long as the drink is cold, it should earn the appreciation of a neophyte and the cautious approval from all but the most curmudgeonly experts.)
For instance, there are those who would have you believe that the most famous applejack cocktail, the Jack Rose, owes its name to a gangster or to a Jersey City bartender or to a flower. It would be wise, perhaps, to suppose that the jack is for applejack and the rose is for its color when made with mass-produced grenadine. It would be wiser yet not to care and instead to devote your energies to discovering which of the innumerable recipes for the drink best suits your sweet tooth or your taste for piquancy.
The trick is in figuring out the most agreeable ratio of applejack to lemon (or lime) juice to homemade grenadine. Don't be daunted by this third ingredient, which is easily concocted by picking up superfine sugar from the grocery store, swiping your wife's pomegranate juice from the fridge, and mixing them in equal parts. If your wife gets on your case about the pomegranate, it might or might not be productive to observe that her juice is pricier than your booze, ounce for ounce. If your wife has used all of your lemons to bleach her sneakers or to discipline the dog, then bear in mind that you can old-fashionedize your Jack Rose—outmode it, you might say—by using a dollop of grenadine, a few dashes of bitters, and a slug of applejack to create a firm and plummy number.
That covers the Jack Rose. Or it would if I weren't obliged, according to tacit rules of pseudo-literary drinks scholarship, to mention that Jake Barnes drinks these in The Sun Also Rises. I will add that the greater challenge in this field of endeavor is to discover a major cocktail that does not appear in the oeuvre of this most ecumenical of literary alcoholics. If Papa were still around, his matadors would be drinking vodka and Red Bull.