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I can't say for certain with some of these, but this would be my best guess:
Gen3: Super Mario Bros. 3 most likely. Other possibilities would be SMB1, Mega Man 2, Mega Man 4 and Kirby's Adventure
Gen4: A few possibilities. Donkey Kong Country, Mortal Kombat 3, Final Fantasy VI.
Gen5: Final Fantasy IX, Tekken 3 or The Legend of Dragoon.
Gen6: Final Fantasy X, Tekken 5, Super Smash Bros. Melee or Soul Calibur 2.
Gen7: Super Smash Bros. Brawl without a doubt. After that maybe Valkyria Chronicles.
Gen8: Bloodborne or Dark Souls 3.

I left out PC games since you can't really split them into different generations.On PC I've probably spent the most time on Red Alert 2, League of Legends and Total Annihilation, although there are a number of other possibilities as well.