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Chrkeller said:

Dreamcast was the biggest jump in 3d gaming. I get the gamecube was more powerful than the Dreamcast, but DC was first. The jump to Soul, Dead or Alive 2, Code Veronica, Skies, etc was massive.

So I guess my answer is N64 to Dreamcast.  It was the first time where I could see where 3D gaming was going.

Dreamcast isn't the successor to the N64, Gamecube is.