I’ve never really acquired a preference for drinking pete moss, but the few that didn’t make me want to puke were 15 year and older. Glenmorangie and Hyland Park come to mind (both of which I brought back from the UK). The 19 YO Highland Park was actually quite good; still reminiscent of potting soil, but good nonetheless. My scotch drinking friends were about orgasmic when they tried it. I'm pretty sure that one's well over a hundred in the states though.

I think the first thing you need to do Rick, is find out if he likes single malt or blended. Big difference between the two and the single malt guys generally take offence at even the notion of drinking a blended scotch.

If he likes blended, Johnny Walker Blue will be much appreciated. Sometimes you can find it under a hundred.

If he likes single malt, I’d just wander around a few liquor stores and find one 15 years or older that’s in your price range. Big scotch fans are like wine drinkers, they like to try new ones as they all do vary in taste. Your friend will appreciate the fact that you got him an aged one more than the label (within your budget). Some scotches go for well over $1000 a bottle.