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Not to be a bourbon nazi, but Jack is Tennessee Whiskey, not Bourbon (there is a difference).
My preference is Weller's Special Reserve. It's a 7 yr. old that leans towards the sweet side and is way smoother than a lot of the "top shelf" bourbons. Actually, Weller's Special Reserve used to be considered a "top shelf" before all the fashionable bourbons came out (Woodford Reserve, Knob Creek, etc.). So if you want to try it, don't let the lower price scare you away. 7 yr. old Jim Beam used to be my favorite before I found Weller's.
IMO, Maker's regular bottle (red wax) is a good bourbon but not a great one. It's more marketing than anything else.
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