I remember smoking cigars when I was a teenager in the 80s. Swisher Sweets, sometimes a Dutch Master. I did the thing someone earlier mentioned about biting the end off it like Clint Eastwood (cause that's what you're supposed to do). I didn't realize that it had a hole in the end so that you didn't have to do that.
My first premium was in the early 2000s. A client gave me (sorry, "gifted" me) a sampler from Holt's. I appreciated the thought but left them sitting in a ziploc bag for a couple of months because I wasn't a cigar smoker. I eventually tried one, and it was SO MUCH BETTER than the crap I smoked as a teenager. Holy Cow! I also remember my mouth watering like I had rabies or something.
I don't remember what was in the sampler except for a Connie named Ramundo. They were a house blend at Holt's that were pretty good. It was a bundle cigar, but not inexpensive. Alas, they don't sell them anymore.