I spent a shit ton of hours talking to Pikachu in "Hey You Pikachu" for the N64... it was epic
Pokemon Channel was also a huge waste of time that was pretty entertaining!
Not sure which 'traditional' version I pumped the most hours into.
I think I played Silver the most, last I remember it was about 800 hours.
I might have played more on Ruby but some dude on the bus stole my GBA SP and Ruby (yanked out my hands and ran) on my 19th birthday... so I'll never know.
I played less Fire Red then Silver. I feel like I played Silver forever.