Surprisingly floral and dominated by vanilla, this is an oddly refreshing drink. It is predominantly sweet with a little bit of smoke undertone. If that's what you want, it isn't bad, but the sweetness overpowers the traditional richness and fullness that one expects in a bourbon. There is some woodiness and then a strong floral flavor. This is by far the most floral whiskey I have tasted and while I enjoy it, its lack of depth and strong floral notes make it hard to drink much of this. The finish is long and tasty, but also quite floral. It seems good for mixing, but gets tiring quickly if drinking neat. I'm skeptical that this is as good as regular Jack Daniel's. It's sweeter and smoother, but more muddled with some of that Woodford Reserve banana (a lot, actually), but avoiding the Woodford Reserve harsh gasoline character. The dominant flavor is banana sweetness, though it is backed by a decent amount of tartness that avoids being obtrusive and some bit of corn. There are suggestions of other flavors like a tiny note of tart cherry and a hint of cocoa, but they're hard to find. It's really quite bland, though it is definitely drinkable despite the banana. In comparison, the Woodford Reserve is more full of flavor with more rich grain, smoke, and spice, but also more youthful harshness, alcohol flavor, and watery mouthfeel. They're different,but of similar quality. I might slightly prefer Gentleman Jack somehow, but that isn't particularly a compliment. That banana is way out there, but there is some spice that avoids youthful harshness and at least it's smooth. Regular Jack Daniel's has more complexity with the added rich graininess it brings. Gentleman Jack does have a bit of spice, but the regular Jack mixes its flavors nicely without leaving them muddled and it really showcases its grain in comparison. The regular Jack is richer while still being light. It shows a tad of alcohol, but not too much. Conversely, this has more sweetness with added banana and vanilla, but 5he flavor profile is out of whack. Between the two, I honestly think I prefer the regular Jack. Definitely by a point; likely not by more than two. The single barrel knocks the socks off of both of them in every way though. It is a really nice whiskey to sip. They are not.