I always start folks with Maker's Mark, then progress to Maker's 46 to show the effect finishing staves can have on flavor. After that, it's all about how much you want to spend. Eagle Rare from Buffalo Trace distillery is excellent and can be had for around $35 depending on where you live. Blanton's, also from Buffalo Trace, is great, too, and you get fun pewter horses to collect. It's more expensive, around $60, and hard to find depending on where you live. Michter's is solid, and that's around $30. Woodford Reserve Double Oaked, usually around $60, is as smooth and vanilla-flavored as they come, which is right up my alley. I had Jefferson's Aged at Sea (Voyage 17) ($70 near me) which tasted like scotch. Not a bad thing. I don't spend over $100 on bourbon, for better or worse, so I can't help you too much on the high end.