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The 3DS actually makes a great case here, I never expected that back when it released, but it has a wide library with great games. Among them a handful of all-time favorites for me. Without a doubt the best system of this generation and the best handheld in a long time.

I never really got into the DS as much. Obviously the system had a gigantic library, but relatively few ever interested me. I own less DS games than 3DS games and even less of them would I consider on the same level as my best 3DS games. Still, good times to be had.

Long had I considered the GBA to be quite mediocre, and it is my least favorite of the handhelds. It never got an original Mario game and it has one least favorite Zelda and Mario Kart games. Most I played on the system were ports of good SNES games. In hindsight though I did miss out on some what turned out to be awesome games like Metroid Fusion and Fire Emblem The Sacred Stones, but by then the damage had been done and my interest was elsewhere.

Now the GameBoy and GameBoy Color I had tons of fun with back in the day. My library is the biggest of all my handhelds and there's some games here I was genuinely addicted to. Good games, good Mario games, good Donkey Kong games, Pokémon, smaller games such as Alleyway and the definitive Tetris, some among my all-time favorites but still on average probably inferior to the 3DS. So 3DS wins? Well there's a catch. GameBoy is home to the pinnacle of handheld games. Zelda: Link's Awakening. The game's absolutely brilliant, and puts it's big console brother, even though that one's also among my favorite games, to shame.

So it's 3DS with a high overal score, versus GameBoy with an above decent score plus the absolute high-point. The question becomes, if I had to choose one, would I rather have all of the 3DS, or Zelda: Link's Awakening?

GameBoy wins.