If he's drinking "rail" whisky, it's certainly swill, and probably a blend. (which can be great, but not the rail selection)
For the money you have to spend, I would suggest getting 3 bottles in the $50 price range. Go to a reputable liquor store and ask for assistance.
You can get him 3 different styles, both introducing him to quality whisky and helping him determine what style(s) he likes.
Off the top of my head I would say
Macallan 12 (light, sherry, crisp, quality). Maybe a Balvenie double wood instead. I prefer the Balvenie.
Laphroaig 10 or quarter cask (big, powerful, smoke, brine, iodine, Islay, did I say big flavor?)
Highland Park 12 (honey sweet, smooth, drying, some nice smoke, a classic)
You should find all of these at a good liquor store without difficulty.
When in doubt, ask for a speyside, Islay, and other.
There's really no need to spend a lot on one bottle he would probably not appreciate anyway. With my approach, you can learn together. When you taste them all a few times, you can decide what you like, and go from there.
Good luck, you're starting an interesting adventure together!
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Last edited by TheEtherMan; 11-30-2010 at 05:29 AM.