Pokemon takes the win because of the games, though I always heard from friends that the Digimon tv show was much better.
Pokemon were the ones I have fondest memories for. I played the games, collected the cards, and watched them faithfully every Saturday on FOX and every weekday after school. I also watched the hell out of Digimon digital monsters because Digimon are the champions. Great, now I remember FOX's saturday morning lineup with Yu-Gi-Oh, Jackie Chan adventures, X Men Evolution, and a few others. Oh how I miss the good old times.
Pokémon. That shit was my childhood.
It kind of sucks after the Johto stuff though. A new girl replaces the old one, Ash wrecks her bike and the story largely repeats itself, or so I've gathered from reading stuff on wikis and the like. The manga is where it's at, apparently. I need to check it out.
Never really liked Digimon, the theme song is pretty great though.
Best Cartoon Show - Digimon
Best Video Game - Pokemon
Best time screwing with people who did the card game - Yu-gi-oh
Man I remember all the times my friend stole other people's Yu-gi-oh cards and then selling it back to them like 2 days later in freshman year of high school. I never played Yu-gi-Oh but it was funny to watch as they would look through their deck saying "Man I could've sworn I had this card".