Just because something is high priced doesn't mean you will automatically enjoy it. Rather than spend $180 on one glass paperweight ... I'd suggest trying several different mid-priced bottles.
Scotch is a far different animal from JD. Try Aberlour, GlenLivet or McCallan 12yr. These are all single malts and are in the $25-$40 range. They are easy to drink straight up or with one ice cube.
For blended scotch, JW Black @ $25 is just fine ... or JW Gold @ $60 if you really want to splurge. JW Blue is way overpriced.
For bourbon, I'd recommend Van Winkle 12 or 20yr, Blanton's or Rock Hill Farms Single Barrel. All in the $40-$50 range