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That's a hard one. Back in the day I used to play with my neighbor and friends almost everyday. We would play games like nfl blitz, power stones, marvel vs. capcom, soul calibur and shenmue on dreamcast and goldeneye, zelda, ssb, and mario party on the n64. Before that I would play dozens of games against my dad on snes.

So the funnest would have to be between dreamcast, n64 and snes.