It's 1999. Depending on which half of the school year it was (I suspect "latter"), I was seven years old. My access to the "outside world" was limited, so for the most part, I only heard about the Latest Thing(TM) if it was on TV, in my comics, or being discussed at school. The latter-most is how I recall first hearing about Pokemon; I distinctly remember one kid doing his best Koffing impression, thereby making Koffing one of, if not THE, first Pokemon I knew by name.

Some time later, Mom gave me my first-ever Pokemon plush: Hasbro's bean bag Pikachu. This is where my attachment to Pokemon well and truly took hold; that Pikachu would be one of the highlights of my life for several years afterward, even as he was joined by many other plush/figures/what have you.

My memory's pretty fuzzy timeline-wise, but I seem to recall that Mom gave me Pikachu to soften the blow of learning that we'd be moving again. Dad was still in the Air Force at that point, and if there's one thing the Air Force does with great abandon, it's yank entire families around the country by their collective nose; our current house of twenty-six years was the fourth I'd lived in.

By contrast, I clearly remember that I got ~~MonColle~~ "Battle Figure" Jigglypuff and Wigglytuff right as we moved into our current house. Spearow and Fearow weren't too far behind--I'd been playing with them in my bedroom, sitting on one of the many moving boxes that had been temporarily piled in there, when Dad brought home Pizza Hut. (This was also back when I could eat from Pizza Hut.)

As far as the anime went: I'd been aware of Ash and co. before we moved, but I don't think I actually got to see them in action until after, when we had some tapes and Pokemon: The First Movie on DVD (one of the first DVDs we owned and played, once we got a working player). For whatever reason, I think my brain wanted to conflate Misty with the animated version of Lydia Deetz before I learned the former's name--and no, I don't remember what fake names I saddled her, Ash, and Brock with.

The rest of my collection grew over the course of late '99 to around early 2003. Notable aspects besides the games themselves include the revised Pokemon Handbook, the first four issues/chapters of The Electric Tale of Pikachu, both versions of that Print Studio software, and a good chunk of the legendary Burger King promotions for the first and second movies.

Unfortunately, I was largely shut out of Gen III by a combination of not being able to get Ruby and/or Sapphire and not liking the figures/plush for it as much. It didn't help that Gen III came right as I was about to become an insufferable middle schooler. :U I'm not sure I ever completely, 100% fell off of Pokemon--Gens I and II were still my "wistful comfort things"--but it would be a while before I properly got back in.

Some miscellaneous things what I've dredged from my sieve-memory:

Yannow those fake names I mentioned up there? Eevee's was... "Jaxine". Don't ask.
I think my second bean bag plush was Eevee (if not, then Jigglypuff). For certain, I caught a glimpse of Eevee's underside in one of the moving boxes, meaning that she'd physically been in our previous home.
I was/am a fan of Sailor Moon, and have been so for longer than Pokemon (Sailor Moon reaching Western shores first and all). One of my many childhood crossover ideas involved Ash and Misty becoming Sailor Guardians somehow--Ash was Sailor Earth and Misty was "Sailor Ocean". This one sticks out to me because I know I drew over a colouring book page of Ash to turn him into Sailor Earth, possibly including a doodle of the Earth Badge (GEDDIT)--but that book is currently lost in the depths of our basement.
Pokemon frequently showed up in my comics, mostly in its many adverts--and a 1.5-page parody in Looney Tunes #69.
You know how many of those "metallic" Charmander, Chansey, and Poliwrath figurines I had by the time that Pop-Tarts promo was over? More than one each.