I look instead to the cigar's middlings -- its secondary notes. Mayhaps a secondary note I'd like to see more of. A heavy Maduro whose fruit needs pulling out would do nicely with a snoot-full of Blackberry Manischewitz, for instance. Also, I would recommend not pairing a cigar's under-belly; I'd not want to rise up a stogie's back-bone nor tell you to eat manure twixt puffs. Although it would be a full hoot and three-quarters to see ya going 'down on the farm...'
Thusly, below are some dos and don'ts you perchance may do well to keep in mind. Also, a lot of this pairing thing is you tinkering round a bit. Exploration. Also also and finally, I am writing re: pairing in such a focus as to high-light the cigar.
Indigestible pairings:
Coffee/Espresso
The King of coffee pairings. Do a dark roasted and strongly brewed coffee of a medium or greater strength. Lighter blonde roasts may seem perfect with some milder cigars, but whilst strong coffee is a bitter note -- weak coffee is a sour note. Do not amplify and/or high-light sour notes. A little sour goes a long way, gentlepersons, but I am not here to discuss marital woes. To hit lighter cigars well, employ cream and, to a lesser extent, sugar.
Drink the brew independently and familiarize yourself with its notes. Pair what smacks ya there, to the middlings of what you'd like to light. A note: there is no 'espresso roast' regardless of what your coffee packaging might tell you. Espresso is simply a brewing method. Meaning that the notes of the roast will be mainly unchanged whether prepared in a perk, drip, press, pour-over, or espresso manner.
Chocolate.
Easy-peasy, gentlepersons. Whilst the King is coffee, the Queen is Rupaul... No. Chocolate. Before we delve, lemme just say one thing: mocha latte is not the answer. Mixing the King and Queen in frou-frou froth doth not a Prince make. Or at the very least, said Prince will me a mottled mess.
Try milkier varietals with milder stogies and match the darkness of the wrapper to the hunk a' chocolate on-hand. A bonus of chocolate is that having a bit of its sugar in yer belly will off-set any cigar-drunk or green you may suffer.
In brief and broad strokes: Candela: white chocolate, Connecticut: Couverture (a chocolate heavy in cocoa butter). Habano/Corojo: Milk Chocolate with an eye on matching milk-levels to the cigar's piquancy. Maduro/Oscuro: Dark or Bittersweet chocolate. The more Ligero, the more Bittersweet, as it's vanilla attachment shall be lovely.
(Fortified) Wine.
A note: if the liquor store you find yerself in labels the section "Fortified Wines," you are in the ghetto and one store over is more likely than not a gun shop. If the section reads "Dessert Wines," wait for the soccer mom in front of you to pick her poison, then commence to pay roughly 20% more. Either way -- watch yer wallet.
Fortified wines arose in Portugal as a way to better keep wine for its journey, by infusing it with hooch. Distilled spirits. Every cigar loves a Tawny Port. Sherry is sadly over-looked -- don't over-look it. Whilst not a fortified wine per se, Manischewitz is a lovely cigar pairing. I only drink Kosher Wines.
Manischewitz Wine Chart:
Candela: used ta' pair well with Loganberry. Loganberry is no longer available. Candella/Connecticut: Concord Grape; think of cutting it with Seltzer to make what I call "Manipagne." Habano/Corojo: Cherry (yum). Maduro/Oscuro: Blackberry.
Whisk(e)y
Because I won't even try to convince you otherwise.
You'll be scorching yer taste-buds with hooch.
Good luck tasting a cigar.
Atmospheric pairings:
Jazz with a floral cigar.
Careful with Jazz -- much of it sounds like what happens whenst the Special Ed. class gets itself locked in the band room. Blues with a San Andres wrapper. American Songbook is the Klezmer of the Goyim -- insofar as it'll go with any cigar. A baseball game on the radio. Black and white era films. The Three stooges.
Indigestible pairings:
Whisk(e)y. Beer. Sardines.
Atmospheric pairings:
Electronica music. In-laws.
Listen to THIS Kaplowitz To-day episodic installment wherein pairings are too discussed.
