I've bought Opus X, GOF, and other very expensive cigars for "special occasions", but after smoking them, did not consider them worth the expense. I no longer purchase these type of cigars.
My most prized cigars right now would be 3 OR Dirty Rats, 2 OR Feral Pigs, and a few assorted OR T-52s. Prized to me, because they are all original release, which I consider superior to current production, and when gone, can never be replaced. And yes, I do know what they all taste like, as I've smoked many, many of them.
Edited to add: I just remembered one cigar that I've never tasted. A NC Cohiba EV that was gifted to me years ago. IIRC, the gifting party said that it was an OR from '95 or '96. Nothing super special, just the only cigar in my collection, that I've never smoked before. Would have smoked it before now, but I keep forgetting I have it.