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Shadow1980 said:
I'd start with A Link to the Past. It's the pinnacle of old-school Zelda, and I think 2D Zelda tends to play better than 3D Zelda. LTTP took everything that was great about the original and improved it massively, to the point where it's hard for me to go back to the original. If you have an SNES, track down a copy, or just download a copy off the Virtual Console. It's one of my all-time favorite games.

Then why would you recommend this game for him to play first then? Since he wants to beat them all ;)