I realize this is an old thread, but for the OP and any others curious about getting into Scotch, Bourbon and Whiskey in general I suggest doing what me and some friends did. We started up a Whiskey club, where once a month a person hosts and the guests all contribute $25-$30 bucks for the menu. Host picks a theme, the bottles and some snacks and a good night is had by all with as much emphasis placed on the discussion as the debauchery (host usually prepares a presentation of sorts for education purposes).
Over time you learn quite a bit about the drink that way, bottles you might like to own yourself, and what to look out for at bars once you know what you like. I'd hardly consider myself an expert but we've been doing this for nearly 3 years on a close to monthly basis and it's been a fun and rewarding journey.
I'd also suggest the absolutely wonderful series of Whiskey reviews done by Ralfy on YouTube, he's a great educator and has lots to say about just about every dram under the sun at this point. Great if you're looking for more info on a particular brand or bottle.
As far as suggestions for newcomers and all-time favorites - Macallan, Balvenie, Glenrothes and Tomintoul are all nice, sweet malts from Speyside that are easy on the palate. Can't go wrong with a Redbreast 12 if you want the Irish stuff. For a little more complexity I enjoy a Highland Park, Aberlour A'bunadh, Ardmore or Springbank, some international brands like Amrut and Hibiki are worth checking out as well. My favorites are the peaty beasts of Islay, though - Lagavulin, Laphroaig and anything by Ardbeg. Especially the Uigeadail, which is still probably my all time favorite.
Bourbon has a narrower window for flavor profiles and I prefer the single malts above but there's still some bottles out there I swear by - Noah's Mill, Bookers, Michters, Eagle Rare (RIP RTD), Four Roses and of course the ever elusive but transcendent Pappy Van Winkle. Hope this proves useful to some folks, happy drinking!
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