I second the recommendation of visiting
http://www.straightbourbon.com/forums/index.php for recommendations.
For me, I would buy 6 different bottles to get an idea of the variations. One thing I can attest is that the variances in taste with bourbon is not nearly as drastic as with scotch whisky. I would buy one from each of the following categories (except the last - buy both) which should give you a good perspective on American whiskey:
Rye-based bourbons:
- Eagle Rare
- Elmer T Lee
- Wild Turkey 12
Wheat-based bourbon:
- Van Winkle 12 Lot B
- Pappy Van Winkle 15 (hands down my favorite non-barrel proof American whiskey)
- WL Weller Centenial
Straight-rye whiskey:
- Sazerac Jr
- Van Winkle Family Reserve Rye
- Rittenhouse BIB
Straight-wheat bourbon:
- Bernheim (only one I know of - and it is very good)
Barrel proof bourbon (Buy Both - they are INCREDIBLE!!!):
- George T Stagg (rye-based)
- William Larue Weller (wheat-based)
This should be a good start...
