Here is a link to a good reference for good cigars:
Cigar Aficionado | Top 25 | 2008
One of the issues in America is availability. IT student makes a great point about the facets of cigars and what you particularly like. My tastes and likes change with what I am drinking or doing at the time. Yard Work, grilling, sporting, etc.. If you have access to Cubans, then the Boliver mentioned in the above site is great. If you need a nice gift, then the Montecristo #2 is the one.
Check with your local retailer for Dominican or Nicaraguan products that are very good.