I have only read LOTR and The Hobbit so those are the only things I know about. It seems to me Frodo was not his favorite, but was the one that he felt the most sorry about. Pippin he seemed to like some times but then Pippin would do something dumb, but they would still have a friendly relationship. Bilbo also he seemed to like a lot, but maybe since Gandalf lived so long that the one he spent the most time with would change with the generations.
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