My experiences with bourbon haven't been that good. I've only had the basic Jim and Jack, Four roses, kentucky gentleman and other 'budget bourbon'. Needless to say, I haven't really enjoyed them neat.
This all changed during my trip to NYC less than two months ago. I wanted to buy some bourbon because it's not widely available here in Finland.
I had a dram of Maker's Mark (regular, with red wax?) in a pub and it was pretty good, but not exceptional for me.
in a spirit shop I asked for recommendations and left with a bottle of Blanton's Single Barrel Bourbon (46,5 ABV %, 2.16.09, barrel 38). This stuff was brilliant compared to the stuff I've had before. It really changed my impression of bourbon in general. The guy also recommended Booker's, but it was a bit more expensive so I skipped it. However, I saw a bottle of Booker's (7yrs 3mo, 62.7 ABV %) at JFK and grabbed it and a bottle of Knob Creek as well. I have only opened the Knob Creek, and it was good, but not as good as Blanton's in my opinion. With a splash of water it improved a bit though.
A friend of mine bought me another bottle of Booker's from JFK a month after I got home. I asked for a bottle of different age, so I got a 6yrs 11mo one at 63.45 ABV %. I cracked the bottle open and I have to say it's the smoothest stuff of this strength I've ever had. Very, very good bourbon and goes straigth to the top on my list.
I also tried Wild Turkey 12 yo (50.5 ABV %) a few nights ago when a friend of mine brought a bottle with him. It was quite raw, but still had a lot of character compared to Jim and John. Pretty masculine, if you like. We drank the bottle, so I guess it wasn't that bad
So, for me:
2. Blanton's Single Barrel Bourbon
3. Knob Creek
4. Wild Turkey 12 yo 101
5. Maker's Mark
I tend to lean more on the sweet side (vanilla etc) rather than the 'coal' and 'raw' one.
The ones I had to left out at JFK were Basil Hayden's and Bakers.
I could also get Woodford Reserve, Jim Beam Black, Evan Williams Single Barrel Vintage, Evan Williams Black Label, Elijah Craig 12 yo (and probably a few else) from a friend of mine who's abroad at the moment.
Any recommendations of these based on my top 5 list? Cheers.