Don't take this personal or anything, but my view on Gentleman Jack's is that it's the whiskey for people who don't like whiskey but wan't to be classier than the riff-raff.
It's like a sweetened JD that comes on slightly smoother but finishes just as harshly, thus making it a palatable whiskey for people who don't like straight liquor to drink straight and pretend to be badass.
My opinions, of course, are, as always, seasoned with cynicism. And too many commas.
I like to drink less of the good stuff than more of the bad stuff.