This is hard for me, but I got to go with:
1. Pong - It kickstarted the genre as a whole. It wasn't the first video game, but it was the first popular commercial one.
2. Super Mario Bros. - It revived a dead video game market.
3. Chrono Trigger - Oh god the music. I've played a lot of RPGs, but to me, this one just barely edges out FF6 as the best.
4. Contra - Kept me "entertained" for hours. I finally beat the fucker a few months ago (unless you don't believe emulators count).
5. For a more modern pick, it's a tie here between Super Smash Bros. Melee and Brawl and Civilization III. Civ III was amazing when it released and, functionally at least, still holds up well today.
Honorable mentions:
Galactic Civilizations II
Guitar Hero III
Most Zelda games
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I'm retired from LetsBeef.
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