Thanks for the request @chuckp, favorite topic always. I added the qualifier of under $100 because that's whatI mostly drink and also a warning--I love thick and leathery Islays so there are a bunch here.
  1. 1.
    Laphroaig Triple Wood
    Where to begin with this one. If you like Islays this is a must try, incredibly complex and sweet with all the intense peat you expect from Laphroaig. I don't consider myself to have a sophisticated palate but I can absolutely discern the influences of the three barrels - bourbon, oak quarter cask and sherry. There is also a less expensive version with a little less wood called the Quarter Cask that is also worth picking up, but start with the Triple Wood.
  2. 2.
    Caol Ila 12yr
    If the Triple Wood is like drinking a campfire, this is the marshmallow you roasted over it. Unusually light and crisp for an Islay, a whisper of lemon makes this my favorite warm weather scotch. Also the only one I ever add an ice cube to. I also learned recently that this one is sometimes used in Johnny Walker blends.
  3. 3.
    GlenDronach 15yr Revival
    Classic Speyside jaw dropper, will run around $90 a bottle and worth every penny. Matured in sherry casks and the sherry nose is intense. It will burn on the first sip but once it settles the flavors are many and spectacular. I like to bring this one out to impress friends with some whiskey knowledge, because it's not often in front of you.
  4. 4.
    Lagavulin 16yr
    Another peaty Islay that's really well balanced and very approachable for new drinkers looking for some smoke. Also notable: Lagavulin is Ron Swanson's favorite and this is absolutely their best under $100.
  5. 5.
    Oban 14yr
    So well rounded. One of the only Highlands I like, wonderfully fruity with very little medicine and a bit of salt, said to come from the distillery's seaside locale. This one pours thick like olive oil and has an eye catching golden hue, beauty all around.
  6. 6.
    Ardbeg 10yr
    Absolute classic and very affordable smoky Islay, I first sipped this in the misty isles of the San Juans on a tip from @elooto and it hooked me. The whole Ardbeg line is beautiful and intense and if you want to step up to a hundred dollar bottle that will define cask-strength for you forever, look for the Ardbeg Corryvreckan.
  7. 7.
    Auchentoshan Three Wood
    I love this Lowland because it has all the woody goodness of the Laphroiag TW without the heavy peat, but so much more character than the other Auchentoshans. I do like their 12 year though as a basic, very light entry dram.
  8. 8.
    Yamazaki 18yr
    Have long been curious about Japanese single malts but was always at a complete loss on where to start. Had a bartender once steer me to this one for its rare use of Spanish oak barrels (most Japanese whiskeys use sherry barrels). Delicious, fruity, pleasant surprise, great entry point.
  9. 9.
    Talisker 10yr
    The Isle of Skye standard and a must have if you're building a cabinet with a range of styles. Known for its smoke it's much sweeter than the Islays and it won't punish you for drinking a second glass. People who love Islays often say this tastes dull but I've never gotten that, it's a great compromise when you don't want the full throated leather of Laphroaig or Lagavulin.
  10. 10.
    Dewar's 18yr
    Generally only keep one blended bottle at any one time and this is my current favorite. Very very smooth for sure but I have to admit, it was probably the marketing they did during EPL games last year that got me hooked. Still worth it if you want a blend.