[Originally published February, 2012 at Manarchy Magazine]

“This week, each one of you has a homework assignment. You’re gonna go out, you’re gonna start a fight with a total stranger.” ~ Tyler Durden

Now substitute “start a fight” with “have a drink” and “total stranger” with “drinking buddy” and you’re right on track.

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In the first article, we covered the very basics of whiskey, how it’s made, and how to sip it right, noting color, smell and taste. This is a man’s world, after all, and the modern man knows when to order a Jack and Coke, and when to order a Highland Park 12 year, neat. And not just because your date will think you’re a genius for knowing how to order whiskey, but because these drinks really are worth tasting.

It may seem that we’re just railing on Jack Daniels here, so rather than give the impression that the Old No. 7 is a whiskey for the undiscriminating palette, let’s take a closer look to see if deserves the popularity it enjoys.

First, the facts. Jack Daniels is made in the Southern United States, arguably the home of bourbon. And while it’s true that all bourbons are whiskeys, not all whiskeys are bourbons. Here’s the straight dope from The Straight Dope:

• For a whiskey to qualify as bourbon, the law–by international agreement–stipulates that it must be made in the USA.
• It must be made from at least 51% and no more than 79% Indian corn, and aged for at least two years.
• The barrels for aging can be made of any kind of new oak, charred on the inside.
• It must be distilled at no more than 160 proof (80% alcohol by volume).
• Nothing can be added at bottling to enhance flavor or sweetness or alter color. (The other grains used to make bourbon, though not stipulated by law, are malted barley and either rye or wheat.)

Now then, Jack Daniels is therefore not technically a bourbon. This is because, before the aging process begins, Jack Daniels is “charcoal mellowed”, literally, dripped through charcoal. Aside from this step, the process is exactly the same as any other bourbon, but it’s this extra step which gives Jack Daniels its edge. So how does the mellowing process affect the taste?

Remember that homework assignment? Grab a glass and find out with me.

Jack Daniels Old No.7 has a soft, golden amber color. When you swirl it in your glass, notice how it clings to the side and then develops what are called “legs” as it drips back down. This is related to the alcohol content and a few other really complicated factors that only a chemist could explain. Suffice it to say, it’s the same with the ladies as it is with the whiskeys, Legs are good, good legs are even better, and it’s all a matter of taste.

The smell of Old No. 7 is where the influence of the mellowing process first shows up. It’s soft, smoky and sweet with a hint of caramel, and even more subtly, vanilla. If you were to do a side by side with a similarly aged (and priced) Kentucky bourbon, you’d probably find Jack to be much more mellow, and slightly sweeter, thanks to the charcoal.

Now taste. Notice how the peppery, wood-smoky flavor hits your palette first, but soon gives way to a nice maple-sugar sweetness: Hot and sweet, and while not exactly balanced, after a few sips your palette makes any necessary adjustments. But notice how long the finish lasts, and how it lingers smoothly even though the first notes were all spice and smoke. This is the charm of Jack Daniels, where it really shines when compared to most similarly priced whiskeys or bourbons. You have to be patient, though, so make sure you give yourself plenty of time between sips to actually notice the finish.

Once you’ve got that figured out, it’s the time to experiment. Try adding a little water or ice and see how these affect the flavor. With just water you ought to look for any sort of citrus flavor that opens up, though this is very subtle and may be difficult to pick up if this is your first time. Ice will chill the drink more than with water (for obvious reasons) and this tends to bring out the vanilla and caramel notes, more so as the ice melts.

Now, to bring it back around to the old stand by, Jack and Coke, consider the flavor of Coca-Cola for a moment. Notice any similarities? Of course, and this is why Jack and Coke is such a great mixed drink, because the slightly peppery, mostly caramelly sweetness of Coke is offset by the mostly peppery (at first) then sweetly caramelly notes in the Jack Daniels. It’s not that Jack and Coke is something a real whiskey connoisseur would never order, it’s that the real whiskey connoisseur knows why Jack and Coke is a better drink than, say, Jack and Sprite or Jack and Orange Crush.

Now if you really want to run with this, then for extra credit, the next time you’re at your local liquor store pick up a bottle of Gentlemen Jack. If you’re not willing to front the extra dough for an entire bottle, most large liquor stores sell small sampler bottles. Or bring a friend along and split the cost.

Now, do a side by side taste test and see if you notice any differences, and also, if you think those differences justify the difference in price. Remember, there is no wrong answer here.

How can you say no to a homework assignment that involves whiskey? “Hmm, still can’t tell the difference. Maybe another round will sort this out. Fill er up!”

Yeah. You’re welcome.

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(See that comments section? Yeah, put your tasting notes there. Do you think I was way off on my assessment of the Old No. 7? Is the Gentlemen Jack worth the extra scratch? Is this all just a bunch of whiskey snobbery? Discuss.)