I’m a fan of The Macallen. I had the 15 year old bottle given to me as a birthday gift a few years ago and that has been my favorite since (though to be honest, I haven’t had the money to indulge lately).
This is quite true, as the results of the thread have shown. Maybe the next time you get him on the phone strike up a conversation about scotch and see what he says about his favorite.
That’s the best way. I’m sure silenus, amongst others here, will be able to help given a preference - whisky drinking tastes are really wildly variable. But WHY are you buying your boss a Christmas present? head explodes
Hey silenus, my local bought a huge batch of malts a few years ago from a hotel that was shutting down. Nothing particularly special, except for a Hillside 30-year-old that they just put on the malt rack. They sold most of the bottle for the regular four dollars-ish a half (35ml). Heh, then some old guy reckoned that the Hillside had closed in 1970, and the bottle had been from a cask that had been laid down at the latest in 1940. After a bit of internet sleuthing it turns out that the few remaining bottles of the relatively young 25-year-old go for about six hundred dollars. Frank who owns the pub laughed when confronted by the evidence, and poured the remaining for the regulars.
Hats off to Frank! That’s class. Never tasted that malt, of course, but I can imagine. 
I’ll have to go with the many others recommending The Macallen 12 Cask Strength. It’s sure to please pretty much all classes of Scotch drinkers. In the blended category, I’ve actually been surprised by how much I like Johnny Walker Gold (not to mention the Blue, but at $200 a bottle may be outside your price range). I used to be very partial to single malts until I tried the Blue, then the Gold. However, single malts always seem to give the impression of being “finer” than blended/vatted malts.
If his preferences can’t be ascertained, I might suggest Highland Park – the late Michael Jackson describes it as the “greatest all-rounder,” meaning that it has something for nearly every appreciator of whisky. Technically a Highland (like The Macallan, Glenlivet, et.al.) it’s distilled in Orkney, which provides some peatiness (not nearly as much as a full-on Islay like Laphroaig, Ardbeg, or Lagavulin). While the Macallan, Glenlivet, and Glenfiddich are safe bets, Highland Park is a bit off the beaten path and is a wonderful, wonderful whisky.
Failing that, I’d also suggest Springbank – it’s halfway between a Highland and an Islay, and one of my favorites as well.
In your price range, you can get a bottle of either whisky that I think he’d really appreciate.
Understand that I’d first try to find out his personal preference.
I’ve had all but a couple of the recommendations above, and I can’t really argue with any of them. I will, therefore, muddle the issue farther but suggesting one more. Dalwhinnie is very nice. I don’t really have a personal favorite – depends on how the mood strikes me – but I probably drink more Laphroig and Lagavulin than anything else. I agree with those who said these are less safe bets than the Highland varieties when you’re buying for someone whose tastes you don’t know.
http://www.balvenie.com/
Balvenie is really nice, with a little bit of water.
Old Pulteney is an excellent single malt as is Tobermory.
Springbank was going to be my suggestion as well. I’d say it’s as safe a choice as the Macallan, in that it’s a bottle that few scotch drinkers are going to actively dislike, and it’s got the advantage of being somewhat more obscure. The advantages of obscurity are two-fold: You might be giving him a chance to try something he’s not had before, and also, you’re showing that you put more thought into the choice than the guy who popped into the local shop and bought the more readily available Macallan.
Also, it’s my personal favorite.
I find most Scotch a little too “peaty”, but our bartender turned us on to something called, no-idea-how-to-spell-it but pronounced phoenetically: Boon-a-habin? I’m sure one of the other Dopers can advise how it’s spelled. I rather liked that - full-flavoured without tasting like band-aids smell.
That’d be Bunnahabhain, which is an Islay but much less peaty than its island brethren like Laphroaig and Lagavulin.
Bunnahabhain. Boon-a-havn. A fine dram.
Ha - that’s a great description!
You speak the truth! A buddy of mine, who drinks almost nothing, tries to do this when he buys me scotch. It always makes me feel good.
Yep, that’s it!
Another suggestion: if you like Scotch, but aren’t a big fan of peat, Irish whiskey may be just what you’re looking for. Jameson’s and Tullamore Dew are good, reasonably priced examples of the style, and are available at most bars if you don’t feel like taking the whole-bottle plunge for your first taste.
I’ll be stoppin’ on the way home to pick up fifths of Highland Park, Springbank and Bunnahabhain. Most of the others I have. These recs are just too strong.
I was recently introduced to Red Breast, another good Irish whiskey. I don’t think I’ve seen it in bars, though. It’s become my default Irish whiskey.
I would heartily second An Gadaí’s recommendation of The Balvenie, particularly their 12 y.o. DoubleWood or 15 y.o. Single Barrel varieties. I think the 12 should probably only run you about $50, the 15 probably more like $100. Those are Canadian prices though, and I’m guessing we probably pay more taxes on booze than you do.
Also, I recently tasted a Bruichladdich 15 y.o. that was very nice. It’s an Islay, but it isn’t particularly peaty. I think it was around $90.
If your boss happens to like Canadian whisky, I’d suggest a Forty Creek any day over a Canadian Club or a Crown Royal. I’m not sure what that would cost in the U.S. (or if it’s even available), but up here it’s only like $30.