The good side of this first: I've been obsessed with banana bread notes in whiskeys lately. So, I had to try this. From that perspective, it has a subtle scent of banana bread on the nose and palate as well. However, what really makes me sink the rating is that it was TOO smooth. I do like to have at least a slight bite in my whisk(e)y. The smoothness factor of Gentleman Jack reminded me of my college days when I would go for a Mike's Hard Lemonade. I kept on sipping because it was so smooth, and I didn't feel the alcohol getting to me until I suddenly had a bit of a buzz going on. To me, this is not at all an upgrade from Old No. 7, but quite inferior to it in my view.