Tennessee's dearer Jacks carry the widest gaps

Tennessee whiskey is bourbon's close cousin with one extra step. The new spirit is trickled through thick beds of sugar-maple charcoal before it ever sees a barrel, and that mellowing is what gives the style its soft, faintly sooty sweetness. Four bottles here, a middle price of $79, running from $56 to $113, and all four wear that charcoal signature plainly. Three of them say Jack Daniel's on the front. What the shelf really shows is a single distillery's ladder, and how much the rungs cost over the whiskeys nearest them.

Start where the gap is gentlest. Gentleman Jack is $66, about 16% over its roughly $57 crowd, the smallest premium of the four. It is the soft, polished Jack, run through the charcoal twice rather than once, so it drinks smoother and sweeter: caramel, a light oak note, a touch of banana, the charcoal there but gentle. If you want the Jack character without rough edges, this is the easy middle of the range and barely a stretch over its peers.