The Game Boy! I got it for Christmas the year it released with Tetris and Super Mario Land. I still have both the system and the aforementioned games.
Honestly, I was never a huge fan of the system and was eventually pretty envious of friends who got a Game Gear. The next handheld I got, I bought myself in High School, which was the Game Boy Advance when it launched. Again, wasn't the world's biggest fan of the system due to the lack of backlighting on the screen. If I did decide to play Game Boy games, I did it on the Game Boy Player on the GameCube when that eventually released.
It wasn't until the DS launched that I truly started to fall in love with handheld gaming. Between the clam shell design, the backlit screen, the backwards compatibility, and the touch screen, it finally made handheld gaming comfortable and convenient and truly gave them their own identity.
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