I have had plenty of expensive whisky and more cheap whisky then I can remember. Always a rock solid contender that I keep in the liquor cabinet is Makers Mark. Regular, 46 or cask strength are rock solid hitters. Great to sip straight or over ice. Alternatively mix well as an old fashioned or with coke and not soo pricy you feel guilty doing it. If you go jack go single barrel, gentleman's is not worth the cost. Other solid choices are to find local 'brew'. Stuff that comes from small batch distillery's. Usually will run $50+ per bottle, may or may not be the best, but it broadens the pallet. If you can find it, Breckenridge distillery's bourbon is fantastic.