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Just smoked a Macanudo that Atlasm and I each got when we visited the new Nat Sherman store a few weeks back. They were cleaning out old lockers and found a box that had to be from the 1960-1970's era. It was a bit banged up but ooverall in good condition. It was okay but only special for its age and not so much for the flavor. It was still kind of fun smoking a cigar nearly the same age as me and thinking about how long ago someone rolled it.
Since I only started smoking the good ones in earnest back in 1998 or so....
Just about 6 Ramon cigars that were made to accompany the Partagas 150's. I had some of each, and that the Ramon's were a little better. What year they were made, I'm not certain but I think is was around 1996.
I was gifted a fiver of Cuban Davidoffs from 1980. We burned through those at a herf. I always worry about cigars that are too old (had a ISOM Bolivar from '92 that was too bland), but both the Cupidos and the Davidoffs were sublime.