So you're new to this whole scotch thing and want to figure out how to hang with the big boys. That's why I'm delighted that you're going to be listening to the baseless opinions of an internet yahoo in his thirties when there are writers who have been drinking scotch for so long that their entire digestive tracts can be considered barrel-aged.
I've maintained in the past that while the “big Glens”—that is to say, Glenlivet 12, Glenfiddich 12, and Glenmorangie 10—are commonly available at every bottle shop, let alone a supermarket, they're all fairly light and close to one another taste-wise. That's why here I want to recommend just four or five single malts that will give you a really nice, broad overview of what scotches can be all about.
1. DALMORE 12
The Dalmore 12 attracts some amount of criticism for the fact that it's both unnaturally colored, chill-filtered, and bottled at 40%. But to me it's a good example of the fact that while the whisky could perhaps be prepared better, none of these qualities keep it from being a damned good bottle in its own right. The Dalmore has big, rich flavors of chocolate and cherry with a little bit of leather to keep things a bit complex. If you're a Cabernet drinker, this is an easy jumping in point. Expect to pay about $45 for the bottle.
2. ARDBEG 10
This recommendation is going to be more challenging than the Dalmore 12, but more forgiving than most other Islay whiskies (namely, the smoke bomb that is Laphroaig 10). Ardbeg 10 was perhaps the first malt that I had that best illustrated the crazy range of tastes that scotch could offer. I liked it before, but having this wasn't just tasty, it was instructive. You're going to get a lot of the smokiness that Islay whiskies are known for, but you're also going to get a delightful amount of sea salt that's in perfect balance. This isn't for everyone, but those who like Ardbeg 10 tend to REALLY like it.
3. Glenlivet 15
I'm guilty of a bit dismissive of the “big Glens,” in general but to me, the jump from the Glenlivet 12 to the 15 is one of the clearest examples of a little bit more spend getting you a lot better quality of whisky. I can't have Glenlivet 15 without thinking of apples and cinnamon. It's a light, fruity, and sweet style typical of a Speyside that remains distinctive enough to bring me back to the glass. Today, I find it a little “thin” at 40% ABV, but the double-edge of that particular sword is that it makes it pretty palatable to the novice. Has even my good-natured criticism stopped me from buying several bottles for myself? Nope!
4. Cragganmore 12
Whenever I need something agreeable and complex at the same time, I think of Cragganmore 12. This is a tad more esoteric in the sense that you're not going to see the bottle around everywhere, but a good store with a sizable selection should have it between about $45 and $55. It's slightly fruity, slightly floral, and has just the right balance of sweetness. I also like Cragganmore 12 a whole bunch because the tastes it provides are big, and completely out of balance with the relatively tame 40% ABV. If people aren't generally whisky drinkers and are extremely alcohol-sensitive, I tend to steer them toward this as a good second glass or for something off the beaten path.
All in all, each of the bottles here strikes a perfect balance to me of being relatively affordable, easily sourced, agreeable to a huge number of palates, and delicious no matter who you are.