First - it's normal for puppies to cry and bark. Responding to his calls will impede his crate training. So..plug in your ears and ignore him. They're like babies, they will cry and cry in hopes you'll pick them up and comfort them. But if you do it too much, it doesn't make them independent or they will never learn that it's okay to be left alone. (I don't have kids, so don't rely on my quote, but I've heard that you just allow babies to cry them out even though you just fed them etc).
He'll get used to it. Always make it a positive thing when he goes in the crate. Hide a couple treats under his bed. Put in a simple toy - I would not recommend any squeakers unless if you don't mind squeaking noise all night.
Every night my dog gets a different toy with her, even though she doesn't touch it at all...it's the scent that matters.
