My kids (3 and 2) love Star Wars. They've seen them all (though 3 was the last we showed them and made sure I watched it with them).
You know your kid's attention span and you know the movies. A New Hope is a safe bet. So is Phantom Menace. After they've seen them all, they'll pick their favorite movies and watch them until you're sick of them.
As much as fanboys bitch and complain about what Lucas has done with the franchise, watching them again with kids makes you realize it doesn't matter. These movies are meant for kids and will be loved by every generation of them until the Earth explodes.
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