I started smoking cigarettes at a fairly young age, but quit (and switched to chewing tobacco) around 20 or 21. I experienced a respiratory injury in my late teens that made smoking quite difficult and unenjoyable.
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I smoked what I could get my hands on as a minor, although had a preference for Pall Malls. I always liked their branding ('In Hoc Signe Vinces' and 'ad astra'). Toward the end of my 'smoking career' I switched to rolling my own (by hand and unfiltered). I sometimes smoked Drum but more often than not I smoked Bali Shag, which I found to typically be the freshest. My recommendation to smokers who roll their own is to purchase some humidor or another (it doesn't have to be an expensive one, they sell [or at least used to sell] humidor pouches that were like a sandwich sized-zip lock bag, perfect for a pouch of rolling tobacco, and helped keep it nice and sealed and fresh]).
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When I was about fifteen I worked with a couple of Levantines (one was my age, one a bit older). They were from Jordan, if I recall correctly. They told me that they were scandalized by American smoking habits ('scandalized' is my word, not theirs). Apparently their standards for the freshness of tobacco were much higher than ours-- they would (so they said) throw a pack of cigarettes away without finishing it if it was deemed too stale. I, of course, had never even considered that something like tobacco could be more or less fresh. But the more I thought about it the more I realized they were right (at the very least, about the staleness of Big Tobacco products). Who knows how long that pack you bought sat in inventory, then on a truck, and then on a shelf? This realization was partially responsible for my transition to rolling tobacco and certain changes in my own habits to secure the freshest smoking tobacco I could.