Here are my five, keeping in mind a moderate budget:
Wild Turkey Rare Breed
Woodford Reserve
Blanton's
Elijah Craig 12-year old
Old Grand Dad 114
Each of those is from a different distilling company and each is distinctly different from the others. There were some close calls, but you said five and only five, so I won't mention the ones I had a hard time leaving out.
Tim


There seems to be a time and place for all ranges of the Bourbon spectrum. 
