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shenmue
The first ever proper 3D open world game is pretty traditional on the surface, but there's a deep sense of weirdness amid the arcade games, billiards, capsule machines and vigilante violence, so you can't easily dismiss it as just a clunky first attempt at a GTA-style adventure. Get after those sailors Ryu, but make sure you're home by 8... It's Shenmue on the Dreamcast!
pokemon yellow: special pikachu edition
Ignorance had prevented me from engaging with not just Pokemon, but all turn based JRPGs up to this point. It was the 21st Century and I had no idea what all this HP AP stuff was, or why elemental attacks mattered. All that changed because of a kids cartoon and a weird yellow gerbil with lightning powers. It's Pokemon Yellow on Game Boy!
command & conquer: red alert 2
The alternate history take on C&C steps out on its own and breaks away from just being a glorified expansion, leaning into B-movie camp humour and quite a bit of sexiness. Ah, Lt. Zofia...
star trek voyager: elite force
We're back in the Star Trek universe, discussing weighty themes like the rights of the individual over the state, the value of medical research carried out on sentient beings, and the fine line between deductive extrapolation and conspiracy theory. So OBVIOUSLY the game is a first person shooter...