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i think my hayday as far as playing pokemon was during when pokemon battle revolution for the nintendo wii had a bustling random matchup community
i wasnt very good (it was 2007) and it was frustrating to go up against players with legendaries (i was of the age where i thought using legendaries was lame) but there were a few moments that stood out to me, like feeling awesome for managing to take out a blissey with shedinja - nothing particularly impressive mind you, even back in the day, but all i knew at the time was that blissey was very popular to use and shedinja wasnt, so it felt like sticking it to the man
i hope the newer games can provide that kind of feeling to a fresher demographic