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This question is rather difficult for me to answer even when I played a lot on each handheld system. The first system I bought with my own money is the GBA and that will always have a special place in my heart. Playing Mario Kart and Advance wars with friends using only one cartridge was great.

The original game boy is the system I blame for my love of gaming and handheld gaming in particular. There is something special with sitting at the exact right place under the lamp to get the clearest picture while trying to retain my castle in Mario Land 2 six golden coins.

For some reason, I never got to play much on my 3DS. I still have a few games that I never finished but also never feel like playing. i figured that maybe I finally got old enough that games don't interest me anymore. Or maybe just that handheld gaming stopped being fun since I still played a lot on other systems.

But then the Switch came along and I once again spend hours and hours in my sofa playing. It is my currently most used system and would be the system i picked if i only ever got to use one system ever again. With the switch my love for handheld gaming resurfaced. It will still probably be my last dedicated handheld platform since my mobile is enough for my gaming needs on the go.

But I will give the victory to the system that i have bought most copies of, DS and more specifically DS Lite. I still play it now and then using my third system and got a new and unused system in a box when the current DS Lite gets to old. What strikes me however when I play the DS is that I actually often use it to play GBA-games, mostly advance wars and fire emblem. But in the DS prime both me and my girlfriend at the time spent whole weekends in bed playing pokémon together and brought it on picnics and to the beach. Great times.
If I owned a GBA-micro, that might have kicked DS down to second place. I love that little system, the screen is so crisp. But DS takes the top spot for me when it comes to Nintendos handheld systems.

Top DS games
1. Phoenix Wright Ace Attorney (all of them)
2. Advance Wars Dual Strike
3. Hotel dusk Room 215
4. Elite Beat Agents
5. 42 all time classics