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Woodrow grows up with in rural Virginia with his mother, Belle, and his father, Everett, who works as a coal miner. Because of this, he seems pretty backward and uncultured to Gypsy when he shows up in Coal Station:
Woodrow was gawky and backward and wore hillbilly clothes that were hand-me-downs from his daddy and his daddy's brother, Russell. Once, when we were about ten, I saw Woodrow, and his pants were too long and too big in the waist, so he had a rope tied around his middle to keep them up. (1.23)
But Gypsy soon learns that Woodrow isn't just a hillbilly. He's also a remarkably interesting and smart kid, and before long, he becomes her best friend. The cousins are soon spending all their free time together and form a super loyal bond. Even when they're not getting along, Woodrow is still always there for Gypsy—even beating up Buzz after he mentions her father's death:
There was talk for months about how Woodrow Prater beat the tar out of Buzz Osborne on the first day of school. (18.1)
Despite the fact that Gypsy thinks Woodrow is a hillbilly at first, she comes to realize that he's much more than that. Her cousin is a multifaceted character—just like she is—and she's lucky to have him around.
Even though Woodrow is cross-eyed and a hillbilly, he doesn't let himself get fazed when the other kids (especially Buzz) try to make fun of him. Instead he acts with complete confidence, telling hilarious jokes and stories so that all the kids come to befriend him:
Granny's phone started ringing off its cradle that evening—always for Woodrow—and it didn't slow down for as long as he lived there. Which proved to me that my cousin was the most popular feller since the country singer Little Jimmy Dickens. (8.32)
In fact, Woodrow quickly becomes one of the most popular kids in town. He doesn't let other people make him feel unwelcome at all, and he doesn't let anyone make other people feel like outsiders either. Woodrow quickly makes friends with the people who are usually ignored, like Blind Benny and the class outcast, Rita:
Woodrow was friendly with everybody, but especially so to Rita Presley, who was fat and always got picked on. He smiled at her and told her that she had pretty hair, which she did, and then when somebody teased her, Woodrow said that was about the rudest thing he ever did hear tell of. (8.6)
Woodrow makes other people feel welcome and included, and in addition to being a great story and joke teller, this makes people like him all the more. He might be funny looking, but Woodrow has a heart of gold.