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To beat the E4? Around 3 to 4 days. Probably due to my level of excitement when I first got the games.
To complete the Pokedex? A few weeks. I don't really remember. :/
The first time I played back in 200x it took me weeks I think.
Now I can finish it in a day in about 10 hours. No cheat, nothing. Just solo play-through.
It took me about 2 days because I just rushed through it and right afterwards, I decided to get all of the Pokemon and raise as many Pokemon up to level 100 as possible before i got sick and tired of the game or when I got tired of looking at that stupid yellow rat following me
I haven't played the originals in YEARS... When my brother was first playing through Red, it took us at least a month because we had no idea what the heck we were doing xD Soon though, I was able to get it down to where I could beat it in five or six days.