So, Jamie’s younger than I am. Only semi-surprised.
The first that I recall was a Danneman Tubo, probably around 89-90 (I was 16 or 17). A buddy and I probably smoked a few a month - obviously the local B&M wasn’t big on IDing customers then. Very old school - located on the square of my home town, primarily a pipe shop with a decent cigar selection. It appears they closed sometime after we moved to Alabama in 2003.
The few times I smoked in college (other than cigarettes) they were primarily Fuentes.
In my modern, more serious, cigar incarnation, my first was a Perdomo Lot 23 Natural churchill, bought at the B&M location I still frequent. Probably around 2008. Started smoking a few times a month at that point, and stuck primarily with Perdomo until I got into a more daily smoking routine and discovered one could purchase cigars online.
I don’t buy many Perdomos these days, but since I still have about 200, I still smoke them somewhat regularly. Coincidentally, I’m smoking a Lot 23 Natural Robusto right now.