I married this list with one inspired by @dev awhile back (had to omit cognac, but that can be its own list). This is is a hard one. I'm going to try and keep it (relatively) affordable (although 50 year old scotch is so choice. If you have the means, I highly recommend picking one up). KIND of in order of preference.
  1. 1.
    Angel's Envy Port Cask
    Doesn't really exist anymore... Actually, anything "port cask" is running out real quick.
  2. 2.
    Tullamore DEW 10 Single Malt
    The scotch drinker's Irish whiskey. Once it's out, it's gone forever, so pick up a bottle (it's really not that expensive [yet]). Aged in sherry, bourbon, port, and Madeira barrels. Shout out to Teeling single malt. Lotta really great single malts out of Ireland recently. Also: Tully Phoenix. Another you can get for a reasonable price that is also no longer being made (plus it has a really interesting backstory). Also, all Tully all the time. "Tully me about it."
  3. 3.
    Four Roses Single Barrel
    Integral part of my introduction to bourbon - an early favorite. They're all delicious, but this one is their best by far.
  4. 4.
    Used to be available only in Colorado. I found a bar in NYC with a bottle and it cost me $22 for 1oz. Now it's more like $14 for 1.5oz. It's bottled by volunteers who write really fun notes on the labels.
  5. 5.
    Michter's Unblended American Whiskey
    Yummm. All their shit is really good. Honorable mention: Michter's Bourbon.
  6. 6.
    The Macallan Rare Cask
    We did a Highland Park/The Macallan tasting with 4 marks and this one took the cake. Uses first-fill sherry barrels and comes off richer and darker than you'd expect in a scotch.
  7. 7.
    Blanton's Gold Edition
    Only available in international markets (try Japan) and certain duty free stores. Just to be assholes. Fun fact: by the hoof of the horse (on the cork) is a letter so you can collect "B-L-A-N-T-O-N-S."
  8. 8.
    Glenfiddich 18
    Gorgeous. Coordinated a tasting with their brand ambassador who adorable told us: "would you say the 'Lo-CH Ness monster? No, you say "Lock" Ness. Don't be a dick, it's Glenfidd'ick'."
  9. 9.
    The Glenlivet Nadurra Oloroso
    Aged in Oloroso sherry casks. Super complex, a great scotch to nurse.
  10. 10.
    Auchentoshan Three Wood
    The 3: bourbon, Oloroso sherry, and Pedro Ximenez sherry casks. Dark fruity/butterscotch, juuuust sweet enough!
  11. 11.
    Glen Garioch Founder's Reserve
    Pronounced "Glen-geerie" because fuck you. Smooth as all get out.
  12. 12.
    Ardbeg 10
    As a rinse or a float in a cocktail - I can't drink that shit straight, it's like drinking campfire smoke. But kinda in a good way...
  13. 13.
    The Balvenie 14 Caribbean Cask
    Finished in Caribbean rum casks (the rum itself is aged at the distillery until the casks are deemed "ready" to hold whisky). Such an amazing spiced element... Was lucky enough to taste some of their older stuff (including the 40). I am so spoiled.
  14. 14.
    Bowmore 15
    Google "oyster luge." The good folks at Bowmore came up with the concept after noticing some subtle briny notes due to their proximity to the sea (I sound super pretentious). Prefer this to the 18.
  15. 15.
    Laphroaig Quarter Cask
    Smooooky deliciousness. I'm a "Friend of Laphroaig." It's free and basically means that you own a foot of land there. When you visit the distillery, they'll give you big boots and you can tromp out and plant your flag or whatever.
  16. 16.
    *BONUS* Lagavulin 16
    Thick and hugely peated! For more info, ask @element75 😘