Let's talk about Whisky and Whiskey. In Ireland it's Whiskey, in Scotland it's Whisky (and in the southern part of America).
Bad Irish Whiskey is horrible awful shite, best used as paint thinner. Paddy (powers) is the canonical example of the breed, and god knows how people choke it down.
Currently in my cabinet I have the following
1 Jamesons gold reserve 24yr
1 Jamesons 12yr reserve
1 Bushmills 16yr three wood
1 Macallan Fine Oak 21yr
1 Laphroaig 15yr
1 Glanmorangie 15yr
1 Famous Grouse (for mixing)
1 Knob Creek 9yr old small batch
1 Makers Mark distillery anniversary special
1 Gentleman jack
1 Jack Daniels
Of them all, the Macallan is the best Whisky overall, and certainly the best Scots whisky. I love a good Scotch, but honestly, scotch is something I only want every once in a while.
For my every day drinking whiskey, I'll take Irish. I like the smoothness of the triple distilled whiskeys. Of what I have, the Bushmills is the best whiskey; the Jamie Gold is great stuff, but the three wood is just a bit better. There's some middletons 50yr old reserve floating around that's even better, but I've never actually seen it in the states, and it's ungodly expensive.
In terms of American whiskeys, the knob creek is a decent bourbon, but I'll take the Irish malt three wood any time over even the best bourbon.
Oh an Jack Daniels isn't bourbon, it's tenessee sourmash, and in my case, the Jack is just as a mixer, and for company who don't know any better.
To my mind Jack is oversweet without any counterbalancing flavor, and has an astringency in it's vapor I find unpleasant. JD just isnt something I want to drink straight; however, those same factors make it a great mixer in sodas, and fruit juices. It also makes a decent whisky sour, if you like your whisky sourmash style (as most Americans, especially southerners do).
I personally prefer an oaked rye whisky, or a pure traditional Bourbon (which is only made in KY). I got the Makers Mark at a special anniversary distillery tour a few years ago. They only sell a few barrels worth every year, and it's wonderful stuff.
Unfortunately, I don't think there ARE any affordable, drinkable, pure rye whiskys anymore. It's pretty much the old maxim; "good, fast, cheap, pick two" translated into the beverage world.
Jim Beam Straight Rye, is drinkable, but it's not cheap; same for Wild Turkey Rye (Oh, and if you like wild turkey, the wild turkey liqueur is an interesting honey flavored bourbon cordial). Sazerac is great, but it's both expensive, and hard to find. Old Rip Van Winkle is also decen, expensive, and hard to find. I've heard that Rittenhouse is decent, and relatively reasonably priced, but I've never seen it. I believe it's only distributed in PA.
Remember, a pure rye is going to be a lot smokier and maltier than a bourbon. It is more grainy and less sweet. This makes it more like Scots and Irish whiskies (though like most American whiskys it's still only single distilled rather than double or triple), which is why I like it.
Also, to my mind, the best whisky sours are made with pure rye.