I keep a lot of cigars but to pick the one(s) that I like best might come down to what I pick up and put back so that I can save them. I tend towards medium cigars and don't smoke a lot of nic bombs.

Montague Lonsdales (6-1/2 x 44-rg) from the mid 1990s, nearing the top of the cigar boom. These were a closeout at $39.95, box of 25, from JR who often sells awful sticks on special (like Flor de Baloney or Tabantillas). I believe that they were a list price (normally means nothing) of $150/box at a time when that was an extraordinary price. The box looked the part and the cigars delivered. I bought a box and smoked a couple ROTT and then ordered 16 more boxes (some in maduro). Should have ordered 100. I smoked them non-stop for a several months and so depleted my stash that I've been nursing the last box of maduros for over ten years. Age hasn't changed them much, they were well aged when received.

I believe that these were made in the Philippines reputedly by an all woman staff of torcedors (no claim that they were virgins who rolled them between their thighs). They went out of business.

I preferred the natural but the maduro is nearly as good. Lightly box pressed, they were startlingly long smoking, complex and subtle. Very consistent during the smoke and from cigar to cigar. Never had to chase flavor, it was in every puff. It took a long time for me to enjoy other cigars after this binge and when I started rationing them it was perhaps the only cigar that I had a visceral feeling of missing.

Not necessarily the best cigar that I ever had but one of the best.