I am currently doing a side-by-side comparison of Black Jack and Woodford Reserve. Woodford Reserve has been my go-to sipping bourbon. I bought the Jack for mixing.

They are closer than I would have expected. The Woodford Reserve is a little smoother and somewhat sweeter, but no "hotter" (in spite of its higher proof). My conclusion: Woodford Reserve is better but not worth the extra price if you're mixing and maybe not worth the extra price for sipping.