I certainly hope us non-cigar smokers can also use this section of the forum to discuss tobacco/bourbon pairings - this could be a great additional section if that is the case. Just to start things off, I like to try tobaccos which geographically as well as gustatorily connect with a specific spirit. In the case of a good single-barrel or small batch bourbon, this might be a good dark-stoved Virginia such as McClelland's Dark Star - very rich, cool and complex, with lemony and dark-chocolate overtones. Try this with Knob Creek or Kentucky Spirit. Or a classic Virginia/perique blend - the most famous is the celebrated Escudo. Nothing but Virginia and perique, spun into a thick rope and compacted, like sailors used to do with sailcloth and tightly-wrapped twine. The taste is honest, medium-sweet, and full of the subtle fig-juice taste and power of the perique. Try this one with Woodford Reserve or Rare Breed. These are pure tobaccos, non-aromatic, without sugary casings to make them burn hot but smell like gummi bears to your kids. I would stay away from the classic English latakia blends - these orientals smell like campfires (the tobacco is smoked over tarry shrub fires, possibly along with camel dung, at least from what all my college friends used to opine), and do best with their logical spirit brothers - the huge, stormy, Harris tweed and sea-spray Islay malts like Lagavulin. Just as an aside - keep a bottle of Talisker Skye malt somewhere behind all the bourbons, and have a taste once in a while. We all need to keep our minds and taste buds open, and "Scotland the Brave" with a pipe and drum corps in the background is a lovely thing to hear while raising a glass.