If you don't drink whiskey often you wouldn't really know the difference. There's a definite jump in taste and quality between JD black label and gentleman. It's still on the low end of the mid grade whiskey though. I prefer knob Creek for my mid grade. Have you had that campfire stuff that @Hank always brings? That shit is delicious.
Have you tried Bulleit Whiskey? That's been my go to lately. the Jack rye i really enjoyed too.