If its the first time Im smoking a new cigar, its water, 100% of the time. If its something Ive had a few times and I know what to expect, Ill crack open a big beer, wine, or some tequila.
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Me too, I love Ruination, but not with a cigar.

I really love IPA's and very hoppy beers, most of which have been listed here, however I haven't enjoyed a good IIPA, or IPA due to all the subtitle flavors in the cigar and the beer. If I were picking a beer to have with a cigar I might try a malt foward beer like Moose Drool or other dark brown ales.
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Can't stand IPAs myself, for my palate I find that, if I want to drink beer, Imperial Stouts seem to pair best for me...but I more often turn to tequila or rum, quality ones poured neat.
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And I Thought "Guinness" Was The Answer!:-)
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I have been drinking Old No. 38 Stout with my cigars lately. Seems to complement them nicely. I think the best answer to a question like this is to forget about pairing in general. Just find a good cigar you like and pick out a good beer you like. You can't go wrong with 2 favorites.
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Don't get me wrong, I love I/IPAs, too, I just need some sort of malt backbone :-)

Presumably aged barley wines? Fresh, they can be pretty hoppy like IPAs and hot like imp stouts, though the latter doesn't seem like an issue for you.
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I like English Style Barleywines, so I tend to drink those more often than American. I also am a fan of Barrel Aged Barleywines, and again those tend to be brewed in the English style.
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Yeah, aged barleywines can be really amazing... JW Lees ages great, and I have a pretty big stock of Bigfoot stashed away. One of the few true American style barleywines I enjoy..
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I see. I've never had an English barley wine. I know Swamphead/CCB did a collaboration barley wine where one did an English (called Churchill) and the other did an American (called.Roosevelt). Never did get my hands on either while I was in Florida.

Stone's Old Guardian is great with a few years on it. I had the 08 release last month at a Stone event in Florida, and it tasted like liquid, boozy bread pudding.
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X2

Before gave up beer I loved the Longtrail Double Bag and A NicaLibre Principe. Quick and delicious together.
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I had a great 2008 Schlafly Reserve Barleywine earlier this year that had notes of marshmellow, vanilla, oak, and creme brulee.
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You can't get any simpler than this:

1) Buy beer you enjoy
2) Buy cigars you enjoy
3) Pull any combination thereof out of your humidor/fridge and you can't go wrong.
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Even a blind squirrel finds an acorn now and then.

:-)
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I am a fan of aged non hoppy barleywines...or dopplebocks. or aged imp stouts with my cigars...or a kolsch can be nice with lighter cigars
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