Gentleman Jack is essentially, Jack Daniel’s that’s been through an additional charcoal filtering process with the goal of making the spirit smoother and mellower. (The distillery even calls it “Charcoal Mellowing.”), Gentleman Jack is significantly smoother and quite a bit sweeter, taking on a caramel and honey notes and a more gentle smokiness than standard JD. In fact, Gentleman Jack oddly tastes closer to a blended Scotch than a Bourbon.