I first played Pokemon Blue around Christmas of '98. I had seen the anime first, specifically the collection of episodes where Ash gets each of the starters, and liked Squirtle the best among them, so that is who I picked.
I didn't got into series till my teenage years during gen 5.my first game was pearl(even thought, platinum was existed when). Because I used to watch DP anime, I instantly picked piplup. I remember dawn's piplup was the cutest thing I had ever seen.
Totodile in Heartgold version. Choosing between the three was really difficult, but I ended up with the adorable little croc! Since I didn't know what team building was, I solo'd through the game until I got stuck at Silver's fight in Goldenrod City. I never actually beat a game with a Totodile until a did a complete playthrough recently.
Mine was Cyndaquill. My older brother got Crystal, and so let me mess about on his copy of Silver for a bit. (No, I didn't delete his save, he'd done that already before he let me use it) Mainly because at the time I thought Chicorita was ugly, (an opinion that I no longer hold,) and my brother had picked Totodile, so I wanted something different. It's still one of my favourite starter pokemon.