I love bourbon. And i think it was bourbon that helped feed my appreciation for cigars since they go together so naturally. I cut my teeth, like most, with Makers Mark and Buffalo Trace. I seem to rotate a lot now, but my usual go to is the often unavailable Eagle Rare. I recently found a 1.75 Liter at a local Binny's and could not get to the register fast enough. The bourbon I really like, and rarely see mentioned on these threads, is Michter's Small Batch. For my taste, its fantastic.
Whiskey is a lot like cigars, for me. I don't really have a refined palate. I can't tell you of leather notes in my cigar, or oak in my bourbon. But i can tell you what i think tastes like sticks and leaves... or swamp water soaked in a bowlers butt crack. For me that means i won't ever pay $600 for a Pappy. I'm sure its better than my $60 Blanton's or Black Maple Hill. But I'm equally sure it isn't $540 better.
My bourbon rec's would be
Eagle Rare
Michter's
Four Roses Single Barrel
Blanton's
Elijah Craig 12