To begin, we sat down to a decadent glass of Macallan 1966.  At 35 years, this elegant but still powerful whisky epitomizes the classic Macallan style, and sherried whisky in general. As anyone who's spent time in Spain will tell you, sherry makes a great apertif -- so the choice of a highly-sherried whisky to whet your palate is a good one.  Plus, highly-sherried whiskies are difficult to pair with food in general, so this is a good place to put one (others will tell you differently, but that's my experience).  

As a basic guideline, reserve your rarest and/or most expensive whiskies for 

First up were shellfish samplers for the table -- succulent pieces of crab, lobster, oysters, clams, and shrimp, along with 4 different sauces.  If you've ever paired whisky with shellfish before, the first thing you learn is that the whisky virtually negates any sauce.  A juicy chunk of lobster eaten right before or after a sip of appropriately-paired whisky can be bliss.

To that end, we paired the shellfish with Highland Park 30 and a 19-year Old Pulteney (bottled by Duncan Taylor).  The Old Pulteney was chosen for its maritime, briny notes, and the punch of spice it delivers -- plus the characteristic fruit notes of the distillery -- and it was a bulls-eye pairing.  Just as you might add some horseradish or cocktail sauce to cold shellfish for some extra sweetness and "zing," the Pulteney both "synced" with the sweet seafood flavors and delivered that extra spice boost that we were looking for.  And the shellfish itself was amazing -- just super-fresh and super-good -- it really couldn't have been any better.

Highland Park 30 is an amazingly delicious, lightly peated treat that stands up incredibly well for its age. We hoped that with the lighter, salty flavors of the shellfish the whisky would shine all the more -- but it sorta did and sorta didn't.  Neither hurt the other, and neither helped.  Since HP 30 is so good on its own, most of the guys ended up enjoying it as an "aside."

It's worth noting that Clynelish 14 pairs exceptionally well with shellfish, for an easy go-to (well, at least it's more likely to be found than the Pulteney).

Crafsteak's lobster bisque is one of their signature dishes -- we found out why with our first spoonful.  It's deliciously creamy, full-flavored without being overly-rich, and mmm-inducing.  The whisky accompanying the bisque was chosen to exemplify how an otherwise average-tasting single malt can blossom with the right pairing.  On its own, the 1989 Rosebank Jewels of Scotland is rather "vanilla" and essentially unremarkable -- but against the bisque, it becomes a winner.  The bisque made the whisky sweeter and more luscious -- and, a sip of whisky before the bisque just made the bisque... indescribably good.  But it already was.  

The key to this pairing is choosing a whisky that won't overpower the bisque's creaminess, and that won't kill the subtler aspects that round out the dish.  A Lowland whisky like Rosebank is a "stage" for the bisque to present itself on.  And the cream in the bisque likewise readies the palate to appreciate the subtler flavors in the Rosebank -- there's something about milk/cream (probably the fat and proteins coating the mouth, plus the fact that it's basic as opposed to acidic) that allows many "flat" whiskies to blossom, becoming bigger and sweeter.

We paired  beautifully-shaved slices of Prosciutto di San Daniele with Jameson's Rarest Reserve. Given the delicate, sweet, creamy flavors of prosciutto, Irish whisky tends to pair very well here due to... well, the delicate, sweet, creamy flavors that are characteristic of most Irish whiskeys.  Like the bisque, but to a greater extent here, the idea is to pair a delicate food with a delicate whisky -- as long as the sweetness levels are compatible, almost any cleanly-fruity whisky can work well in this pairing.  Think of melon and prosciutto and you'll get the idea.  (To note, the Jameson's also went incredibly well with the bisque... and given the lighter but still flavorful nature of the whiskey, it probably goes pretty darn well with anything).

Time for some veggies -- and Crafsteak's roasted red peppers hit the spot.  Cooked to the point of

tenderness without a hint of being mushy, these red slices of heaven both combined and contrasted with Longrow 10, resulting in another perfect pairing.  The smoke in the Longrow stood out nicely against the sweetness in the peppers, even bringing out smoky flavors in the peppers themselves.  And, given the sweetness of the peppers, we needed a younger, sweeter whisky to compete -- it worked beautifully.  Try this one at home.

To emphasize a point, the sweeter the food, the sweeter the whisky; likewise, the bigger the food, the bigger the whisky.  Easy, right?

Folks love Craftsteak's Persian Cucumber Salad -- the simple flavors of vinaigrette, cucumber, and arugula mesh well together.  But those same qualities -- particularly vinaigrette combined with bitter greens -- make a whisky accompaniment tricky.  We paired this with Glenfarclas 21 -- while some thought it worked okay, the consensus was that it wasn't a good choice for pairing.  I'll tell you later what we found goes best here.

We had to try Craftsteak's two signature meats: the Kobe Skirt Steak and the Short Ribs.  For good measure, we also had the New York Strip (domestic prime) and the Australian Wagyu Ribeye.  Not to mention the Mushroom Mix, Cipollini Onions, Risotto, Asparagus, and Potato Puree.

The steaks were, honestly, as good as they can get.  By preparing and presenting them simply -- with no complicated rubs (just salt and pepper), and no fancy sauces slathered on -- the rich, full flavors of the beef burst with every juicy bite.  Steak simply doesn't get better than this.  Different, maybe, but not better.  And the short ribs... ridiculous.

Pairing whisky with steak is actually quite tricky -- you'll hear many experts tell you that the big flavors of steak should go with a big peated whisky, like an Ardbeg or Laphroaig. But I've found that advice more academic than practical -- the peat often just doesn't work.  In fact, many such whiskies don't pair well at all with juicy steaks -- and though we had Ardbeg Airigh Nam Beist here, it was more of a whisky that we drank "aside" the meal rather than one that actually meshed well with it (though some of the guys thought it made a good contrasting pairing with the short ribs).  To note, we'd kept that Persian Cucumber Salad hanging around, just to see if we could find something that went well with it -- and surprisingly, the Beast was the winner here.  The smoky notes played well off the bitter greens and tangy, vinaigrette-covered cucumbers.

What did pair excellently with the steaks was Bowmore 25.  Now, this is already an excellent whisky to begin with -- a Bowmore that's full of rich flavors, but with a smooth elegance to it.  It's that not-a-monster quality that made the steaks and whisky blend together effortlessly.  The juicy, savory steak flavors swirled perfectly with Bow 25's spice, salt, and pepper, all carried by the whisky's light sherry sweetness, and wrapped up in wisps of light smoke.  Yeah, it was really good, and another super pairing.

As an example of a more economical pairing, we also had Glenmorangie Nectar d'Or.  The high level of honey-sweetness in the 'Morangie lends it to pairing decently with almost anything, and these delicious steaks were no exception.  This is another easy one to try at home.

Oh yeah, I forgot -- the sides.  They were all good, but the onions deserve special mention.  We'd never had onions quite like these before... they were truly surprising, bursting with rich flavors, and tender while still having good texture.

With the main meal concluded, it was again time to sample some super-rare, unique whiskies on their own (same rationale as the apertif).  Sitting in Craftsteak's locked glass cabinet were two Celtic-looking MacPhail's decanters, one distilled in 1937, the other in 1938, and each 50 years old.  Since MacPhail's is a bottler and not a distiller, the source of the actual whisky in the bottles will likely always remain a mystery -- but as we've learned, it's not where it's from, it's how it tastes.  And, wow, were these tasty.  And unique!  Though our guess is that they're both from the same distillery, the whisky in each was quite different.  We spent a lot of time discussing the two, comparing and contrasting the flavors, and arguing over which was better.  I was the only one at the table who preferred the '38 to the '37, but we're talking about the difference between A and A- at the very worst.

The meal was capped off with Craftsteak's own version of chocolate lava cake and sticky buns, plus assorted berries (a classic pairing choice).  It's my feeling that sugary-sweet desserts don't go well with whisky -- the excessive sweetness, which is great on its own, tends to make almost all whisky taste bitter in comparison.  Thus, we went with a separate digestif, followed by sweet dessert.

Regarding the desserts themselves, I'm sure you already know what I'm gonna say, so I'll spare you the superlative adjectives.  I want more sticky buns.

Let's just say that we're already wondering when we're gonna go back.

If you're thinking of trying something like this yourself, I'd suggest that you take an "experimental" approach -- with each course, order smaller pours of two different whiskies.  It's more fun to see what pairs best, and play around with your own pairings a little.  Or, you can just take our advice, go to Craftsteak, and order the final menu in the box above.