Like the Cougar Bite, this is an older drink of mine, one that found its way onto the list of the restaurant where I sporadically tend bar. Unlike the Cougar Bite, though, it never did sell particularly well and fell victim to the seasonality of its main sweetening agent. I honestly don't give a damn, though - this is still one of my absolute favorite cocktails.
I think of this as very much a bartender's drink rather than a mixologist's. For one, it was conceived as a way to use up some extra bottles of E&J brandy that had been accidentally ordered by our manager. For two, it's a relatively simple drink, and quick to turn out. For three, it's very amenable to substitution and adjustment, making it really more a class of drinks (like the Collins) than a single recipe.
Here's the original form, the so-called Colonial Pirate:
1 1/2 oz brandy (E&J, as noted above, but any will do, though VSOP-grade or better is preferable)
3/4 oz rich pineapple syrup*
1 large dash Fee's Aztec Chocolate bitters
1 large dash Fee's Aromatic bitters**
Shake the above lightly, strain into a cocktail glass, and top off with about 1oz of dry sparkling wine to taste (Champagne, Cava, California bubbly, whatever you've got).
*This one actually is easy, unlike that damned squash syrup. Bring a syrup of two cups turbinado or other natural sugar and one cup water to a simmer, then pour over a peeled and cored pineapple sliced into 1/2 inch cubes. Let stand for 24 hours and pour through a fine strainer, making sure to reserve the pineapple cubes, as they make a very nice garnish if rolled in additional fine sugar and dried on a cooling rack.
**We used to use a ras el hanout bitters in the restaurant, but this makes a reasonable substitute.
Again, this is a drink with endless potential for variation. Ran out of brandy and need to use rum? No problem - you'll have a Caribbean Pirate (I sometimes name them specifically after the island from whence the rum hails, resulting in the "Barbados Pirate", "Cuban Pirate", etc.) The Dutch Pirate is made with genever in place of the brandy; the Scandinavian Pirate uses aquavit, which results in perhaps my favorite variation. And so on. Vary the fruit, if you like - just stick with a medium-dark natural sugar. Mango makes an excellent alternative, though you should add a dash of lime juice to compensate for the missing tartness. For any of these, vary the amount of bubbly to taste; add slowly, stir and taste frequently. You want to add crispness without overwhelming the drink's spicy, rich texture. I'm gonna go make another one.