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My kids love all of the Hermie and Friends videos. I think the messages in each movie are clear; in fact, Flo the Lying Fly was helpful when one of our kids decided to try deceit out as a preschooler. My all-time favorite Hermie video, though, is the Christmas one: A Fruitcake Christmas. There are a lot of allusions to other classic holiday favorites woven into the storyline.
I read this book to my kids this past fall and they laughed themselves silly! There are a lot of great talking points, and I'm anxious to show them the movie version on a popcorn/movie night during December!
Little needs to be said about Charlie Brown- it's a classic.
I think my husband's grandma gave this video to our oldest one year. If you have younger children sensitive to scary parts, there is one scene where the lamb faces a predator in the middle of the night. All ends well, but it is a bit menacing. Other than that, it's a cute movie.
We also have the book in our holiday basket; the illustrations are very pretty.
We have all four of Liz Curtis Higgs' books in her parable series; there is one for each season. When the children were preschoolers, we read the Pumpkin Patch Parable while we carved our pumpkin. Liz uses a farmer and his family to share the gospel story in each volume; there is a corresponding Bible verse on each page.