Last Christmas. I got hit by nostalgia earlier during the year and I started rewatching the anime, then decided that I could try the games. I got Diamond, Pearl, Platinum, SoulSilver and XD: Gale of Darkness as gifts.
I started in '99 when it was released in Europe. I remember it - I was in primary school at the time, and it was the last day of term. We were allowed to bring in a toy or something to play with and my friend had brought in Pokémon Red. I borrowed it for an hour or so, and I tried to beat Brock with a level 15 Charmander and a load of other, very low level Pokémon. I managed it, and Charmander evolved at the end of the battle. I bought my own Red version a couple of hours later.
Once upon a time, when I was a precocious lad of about 5 or 6, I hated Pokémon with a passion, for absolutely no reason. I think it has to do with my innate dislike towards anything wildly popular (which I have unimaginatively dubbed "Hating Insanely Popular Stuff Through Emptyheaded Reasoning"). Then I read one of Tracey West's junior novelisations (remember those?), I got Yellow for my seventh birthday (right before my family had to make a long trip back from Thailand, which made for a remarkably kickass plane ride), I got Blue, I got Crystal, I got Sapphire for another birthday (possibly my tenth, although that may be wishful thinking on my part) and the rest is history.
If memory serves correctly, my brother and I got our blue and red versions (respectively) in late January-early February 1999. We only had one Gameboy, though, and the fights were pretty intense until I got one for Christmas. Haha.
I remember playing Pokemon Stadium and Pokemon Snap on my 64. And a couple of years later, my mom found a Blue cartridge at a yard sale. It was intended to be my sister's, but I got it because she never played it.
After asking and hoping to get a Pokémon game and GameBoy Color about two years, my parents finally bought it to me in the spring 2001. My parents thought games were too expensive and they seriously thought I would get bored with it soon anyway. Well, still having my Blue version, still playing with it.