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Hmm this is hard.

I'll seperate handheld and home console. I'll also do a PC section. :)

Gen 4
Pokemon Yellow (Super Mario Land is a close second)

Gen 5
Gameboy Colour
Pokemon Gold

Gen 6
Gameboy Advance
Yu-Gi-Oh: Worldwide Edition: Stairway To The Destined Duel

Gen 7
Didn't have anything this gen

Gen 8
Ethier Pokemon Y, Samurai Warriors: Chronicles or Fire Emblem: Awakening, not sure at all.

Home Console
Gen 4
Mega Drive
Sonic The Hedgehog (Moonwalker as a close second)

Gen 5
Playstation 1
Gundam Wing: Battle Assault 2

Gen 6
Super Smash Bros. Melee

Gen 7
Wii Sports (Mortal Kombat : Armageddon is a close second)

Gen 8
Wii U
Super Mario 3D World

Gen 9
The Legend Of Zelda: Breath of the Wild

Windows 95/98
Age of Empires

Windows XP
Star Wars Empire At War/Forces of Corruption

Windows 7
Total War: Shogun 2 or Skyrim, not sure.

Windows 10
Total Warhammer 2