I feel I've been drinking bourbon long enough to make this list of my favorites at any price. I'm sure I have a few blind spots. There are also probably some bourbons that might not make it simply because I haven't had it enough to really get to know it, as one does in the course of a bottle, e.g., a lot of folks like Basil Hayden's, but I've only had it twice--once at a friend's house and once at the Beer, BBQ, and Bourbon fest in Annapolis last year. The prices are what I've generally seen these bottles priced at.
You can't find anything special down here, the goal is something that is enjoyable rather than simply tolerable (or intolerable).
Winner: Early Times 354 Bourbon
This is not the regular Early Times that was not bourbon (as it was aged in reused barrels), this is a new release bourbon. For $15 bucks I was surprised at the fancy packaging, with tasting notes and a cool picture that reveals itself as you drink the bottle down. Was I swayed a bit by the marketing? Sure, but it made drinking cheap bourbon fun, and I found the stuff in the bottle to be enjoyable, too.
Honorable Mentions: Evan Williams Black Label, Jim Beam and Jim Beam Choice, Old Forrester
Winner: Buffalo Trace
Jim Murray, author of Whisky Bible, calls this one of the world's great bourbons from one of the world's great distilleries. I've heard that this is essentially the same whisky as Blanton's Single Barrel which is more than double the price. Tons of complexity for not tons of cash. This is what I would call my "everyday" bourbon.
Honorable Mention: Elijah Craig 12
Winner: Evan Williams Single Barrel
With price taken into account, this may be my all time favorite bourbon. For just 25 smackers, you get the fun of drinking a 10 year old single barrel whisky, hand labeled bottle that is vintage dated, meaning it comes out once a year. I have unopened bottles of the 99 and 00, with an eye for a future whisky party comparing vintages. And it tastes fantastic, a lot of influence from 10 years in the barrel and a nice cinnamon finish.
Honorable Mentions: Maker's Mark, Elmer T. Lee Single Barrel, Knob Creek
Winner: Woodford Reserve
This makes a lot of folks' list of favorites. It's a nice price point when you want something a bit more special than your everyday stuff but not too pricey. It's got just enough burn that rocks may come into play, but not necessarily, and a lot of flavor. Also their distillery tour is great.
Honorable Mentions: Makers 46, Four Roses Single Barrel, Wild Turkey Rare Breed
I love the wooden box, the high proof, and the note from Booker on the label. Tons of character. A lot of fire to it but not so much that I don't get some vanilla from the wood and some leather. It mellows with ice in a nice way. Sweet and spicy finish.
Honorable Mention: Noah's Mill
Winner: Pappy Van Winkle 15 year
Pappy is my all time favorite. I described it in my tasting notes as "puckering." Most wheated bourbons are known for being mellow, but even with 15 years in the barrel Pappy comes out red and fiery. Another great bourbon from Buffalo Trace.
Honorable Mention: Blanton's (the entry level single barrel)
Winner: George T. Stagg
I had to hunt hard to find a bottle of this once yearly release from Buffalo Trace. Would you believe if I told you you can actually sip it at 143 proof? I won't judge you if you need some water, though. The Buffalo Antique Collection is fun, next year I'd like to try another one, perhaps the Weller or the Sazerac Rye (which is incredible).
Honorable Mention: Wild Turkey Tradition