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I've been sampling a bunch of different bourbons lately, and haven't really gone wrong with any of them in the $20 and up range.
Glenlivet Single Malt is pretty classy, at about $35 a bottle. Scotch tastes smokier than bourbon, that's the general difference. The malt is dried by burning peat in the same room.
Woodford Reserve bourbon is quite good. Knob Creek is pretty tasty. These are both under $40, though.
Really, if you just go buy a bottle of just about any bourbon or scotch in your price range, it will be good.
Another bourbon you could try is Elijah Craig 18 Yr - it's quite good.
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re: EvergreenDan
Fantastic recommendation - 2 very different whiskeys, both very good. Plus, I feel that due to the high rye content in Bulleit, it can be used (instead of rye whiskey) in a pinch to make manhattans. If you're willing to spend a bit more, you might also want to get a bottle of something like Maker's Mark, to have a representation of a sweeter wheated bourbon, and a bottle of Glenlivet, as a representation of a Speyside scotch (which is very different from an Islay). Besides, who knows, maybe after trying a wide range of whiskey, you may grow to like them yourself!
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