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NSMBW is too tough for my 8 year old and she beat a few games. I suggest:

Wario Ware: Smooth Moves
Rayman (any of the Rabbids games)
Mario Kart Wii
Super Smash Bros. Brawl

I'm buying Wario Shake It. I forgot about that game and I remember really wanting it (thanks, Croomz!). Whatever you decide, make sure you go on youtube to make sure its the kind of game he's going to enjoy. Don't play around when it comes to making a kid happy. This is serious business.