As others have said, you can’t go wrong with The Macallan.
The thing is… any scotch aficianado will be familiar with that… and a great gift to a Scotch drinker is finding a new treasure.
I just bought an 18-year Tamnavulin. Really a pleasant surprise. It’s a Speyside malt, light teak in color, nutty, medium sweet, with hints of oak. Strongly recommend.
I found a 24 y.o. Tamnavulin recently, a Signatory botteling, then went back and bought every other bottle they had, five in all. Excellent, marvelous scotch (even if it does exceed the $ limit by half again).
If you can find the Highland Park 18, grab it. By far the best expression of an already marvelous malt.
Bunnahabhain is good, but Bowmore 17 beats it hands-down as a “non-peat monster” Islay.
eta: A previous thread full of recommendations and discussion.
It’s above your price range for your boss, but if you ever want to try it for yourself, I recommend Balvenie Portwood 21.
I’m partial to Glenlivet (of course) and Glenmorangie. For your boss, a Glenlivet 18 could be nice. I’d like to get a bottle of Glenlivet Nadurra.
I tried a Lagavulin the other weekend, and while it’s better than most Islays, I’m still not a fan of the peaty band-aids. I am going to pick up a bottle of Bunnahabhain, though.
One thing that may be worth a shot is finding out if there is a store with a really good Scotch selection near you. Then going and asking the Scotch dude(if it is actually a good store there will most definately be one) what he suggests in your situation. Good places are always fighting over getting in cases of this and that, or whatever, that may not be common in the states. And the prices don’t always match the rarity, sometimes it’s just a specie that doesn’t have a good distribution here, but a decent price. And if he got a half-case in of something(that isn’t already reservered for the regulars); Jackpot.
There is nothing a real Scotch guy likes more than trying something new to him, even if he doesn’t end up prefering it. And he will appreciate the effort.
It’s 5 o’clock somewhere, right? As soon as I got home and fed the cats, I poured myself a hefty dram of the Highland Park 18.
Ahhhhhhhh. No better tipple in the world. God loves us.
I’m on the Irish tonight. Hurrah! Happy Hallowe’en. Samhain Shona Daoibh!
Wow. I am envious. I saw the write-up on the 24-year, but I can’t find it in my area at all…
If you ever come to Scotland I’d be happy to show you around.
All in all some very good recommendations that I can’t really add to.
Except that I’ll be pouring myself a shot of Glenrothes in a moment…
I have had a sip of Macallan 25-year-old. You couldn’t possibly go wrong with this,
Yep, thanks to this thread I’ll be pouring myself a wee dram of Macallan as soon as I’m through typing this.
Thanks, guys. 
I’m partial to Knockando myself. Glenmorangie is another favorite.
I think I’m going to Scotland next week. Huzzah!
To receive a fine quality Scotch as a gift… 
Well, I guess this is a resurrection of the thread, but I tried this scotch last weekend:
Lonach “Carsebridge” 43 Years Old Single Malt.
Oh my, what a smooth, delcious flavor, with wonderful aftertaste.
I could heartily second any one of the recommendations already made, but where would be the fun in that?
I am a big fan of interesting finishes in my whisky - at present, I have an Arran that has been finished in a Tokay cask, a Bowmore that has been finished in a Sherry cask and a Caol Ila which has been aged in a Sherry cask,all of which are delicious.
My all time favourite is the Glenfiddich Gran Reserva. Now, I couldn’t give a toss about a regular Glenfiddich, it’s too light for my tastes, but the Gran Reserva is a special expression which has been aged 21 years in a Cuban Rum cask. It is superb. Sadly, it is not available for sale in the USA because of the Cuban rum cask. So, if you really want to impress your boss, pick up a bottle the next time you’re out of the country. I do know it’s available in Canada.