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I watched one episode of Bayblade when I was really young (I think that is an anime) but the first time I actually watched an anime was probably Pokemon DP, the very first episode of the season, then went on to Naruto after knowing what an anime was.
The very first anime I've watched was Speed Racer, and boy, the things I saw on that show make me shudder to this day. Yeah, the dubbing was ridiculous and the animation was bad (the show was made in the late 60s, what do you expect), but some of the death scenes were quite gruesome. One episode that really stood out to me had one of the races take place in a volcano, and the villain of the episode had molten lava splashed on his face! Yeesh!! I was around 8 or 9 years old when I saw that.
Sailor Moon was another show I watched as a kid, but I don't think that was my first since whenever I thought about Japanese animation as a child, I would always think of Speed Racer. I remember really getting into Sailor Moon in high school thanks to a friend.
Of course, my first exposure was on the cartoon channel as a kid, like so many others. I actually avoided watching Sailor Moon most of the time, since it was "too girly." I did keep up with Pokemon, Digimon, and Dragonball Z religiously, though. I eventually ended up seeing some or all of everything that aired on Cartoon Network during that period, including the Adult Swim time block. But everyone watched those, because that's what was on the TV, so I don't really consider that the start of my journey into anime.
Once I got passed down a computer for my personal use (I was around 12), I ended up downloading some anime to watch myself. But these were all things I had seen on TV before (Inuyasha, Fullmetal Alchemist, Rurouni Kenshin, Cowboy Bebop, Tenchi Muyo, to name a few). It was pretty funny: my HDD was a whopping 10gb, so I had to delete a series in order to download a new one. But I digress.
The first series I actually discovered on my own and then watched was either Elfen Lied or Air. I sadly can't specifically remember which I saw first, but it was around the same time. In my mind, that's where "it all started" for me.