This question is really hard for me to answer. All my game experiences have been Ninten handheld wise. I saw the Game Gear and the PSP/Vita, but don't have much experiences with them. From the grey brick to the 3DS, I've had great times with them. Mario Land 1 and 2, the RPGs from every handheld of theirs, the first time playing pokemon and loving Silver/Gold so much, The Sonic games from the GBA, the new games possible on the DS, like TWEoY, Rhythm Heaven, and Trauma Center, and the awesome new games on the 3DS. All of them brought me so much joy.
For me to pick just one, well, I'd have to dig through tons of games, and I don't have time to do that... TwT



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