Don't pull this string. It inevitably ends with YOU playing Kung Fu Panda (or whatever game you decide on) when he gets stuck.
With that said, the first game nm my daughter ever beat was The Maw on Xbox 360. She started off with Super Rub a Dub on PS3 (a motion controlled game). Then moved on to Feeding Frenzy on Xbox 360--basically all you needed was the analog stick. I told her "Eat the fish that are smaller than you. Don't touch the fish that are bigger than you." And then I can't home from work one day and she had completely beaten The Maw. She was so proud!
Also know that, before long, she was playing GTA and being my co-op partner in games like Super Mario Galaxy and...uh Resident Evil 5. Kids don't want kid's games. They want to play what you play because what you play looks cool. But yeah, my original point: Whatever game we pick will be there game that YOU will be playing as soon as the kid gets stuck. Try a co-op game like Castle Crashers or Golden Axe. I have two nephews age 5 and 2. There's a reason games like that end up in my "Recently played" games in my sig.
