It has been a while since I smoked anything with less than 5 years on it. Keep in mind that I mostly smoke Habanos but I do smoke some non-Habanos also. I feel that the more age on the cigar the better the flavors meld together resulting in a smoother more well rounded smoke.

As far as aging cigars for a very long time, I have some Clear Havanas (cigars made in the U.S. with Cuban tobacco before the embargo) that are from the 40's and 50's. The are pretty darn good smokes.