Old World Palate

I'm guessing we've all seen a humidor at our local wine shop and thought, "hmmm, maybe I'll get cigar tonight and try that out.  But how do I pair a cigar?  Or do I even need to?"  Well firstly I'll say 'yes' you should get something to pair your cigar with.  Aside from providing a good compliment to the cigar flavors, a drink also cleanses your palate and helps you avoid a lingering bitterness that often builds up throughout the course of smoking.  This is especially true if you're like me and rarely smoke. But before we get into pairing advice, let's take a look at a few things you'll need to properly smoke a cigar:

• hole puncher/cigar cutter You are probably already familiar with cigar cutters if you watched just about any mobster movie in the late 80s/early 90s, as they were invariably used to cut off some poor schmuck's finger.  Surprisingly they can also be used to cut the tip off the smoking end of a cigar.  Hole punches are similar to cutters, but have the benefit of creating a much larger surface area to pull smoke through, and thus making your cigar easier to smoke.
• smoking jacket You may think this is a joke, but if you don't want to spend the rest of the night reeking of cigar smoke, you should seriously consider wearing a smoking jacket.  So where do you find one?  Well I'm sure you could find one at your local big-game hunter supply store.  Or you could build a time machine, go back to 1870, and borrow one from the first banker you stumble across.  Or you could just put on a jacket or sweatshirt that you don't plan on wearing for the rest of the night.
• monocle/top hat Okay, this is a joke.  No one needs a top hat or monocle, but if you build that time machine it could help you blend in.

Now that we're all set on the cigar side, let's talk about pairings.  In the case of cigars, one should really be thinking "like with like."  Cigars are strong and bitter and can easily overpower most beverages.  This is why the traditional pairing with whiskey or port is so prevalent.  They are both fantastic pairings.  Regarding whiskey, a good single malt from Islay brings a bit of peat and smoke that naturally compliments the character of  a cigar and particularly the stronger maduros.  If you want to take more of a "contrast" approach or are looking for something a bit sweeter, then you may want to go with a Highland/Lowland Scotch or Bourbon.  Ports add a large amount of sweetness and a strong rich fruity character.  They certainly have the intensity to match a cigar, but are a bit too rich to provide the palate cleansing effect.  But if you are already a fan of port, that probably won't be much of an issue. Those are all more traditional pairings, and with good reason.  However I have to say that the most intriguing pairing for me lately has been beer.  Your first thought may be that beer is too weak to handle a cigar, but I beg to differ.  Beers with a lot of hops, roasted malts, and/or higher alcohol can be extremely hardy and certainly up to the task at hand.  Some recent pairings I've had some great success with are Rogue's Brutal Bitter and Chocolate Stout as well as the Old Rasputin Imperial Stout from North Coast Brewery.  All of these are American brews, which tend to be very hoppy and in this case is a big plus.  But don't count out similar styles from other countries and the darker ales form Belgium such as the Delerium Nocturnum or Chimay Blue.  Additionally the relative low cost of beers allow you to experiment with ease without have to shell out $25 - $50 for a good bottle of port or whiskey.  Just buy and single and go for it.