I started back in early college days (so figuring 18-19ish years old?) with a buddy, who swore by 7-11 strawberry phillies. Of course, being the good boy I was I never knew what they REALLY were used for but I started off my cigar path with them if you even want to call them "cigars."
It was up until I took a pack to my Uncle's house, who at the time was big into cigars. He was like you aren't smoking these things anymore unless you want the devils lettuce. And gave me a Macanudo cigar to try. From that point on, I got kicked off the cliff head first and never looked back. We'd go to the local lounge a couple of times a month together, catch up on life and just enjoy the bonding. Unfortunately, due to some health conditions, he's had to drastically slow down on his cigar smoking but when we do get together, we make it a point to have at least one over a libation and reminisce on the good old days. And our words to each other at some point in our cigar smoking is always, "Hey, you can never go wrong with a Macanudo" because that's the cigar that got me started down the slope. Even to this day as my palate expanded and has changed, there's always a once in a while time I feel the need to grab a Macanudo for old times sake.