Envy. Woody’s envy of Buzz drives the first Toy Story. He can only be a Heart Type.
Woody’s a great leader. He’s got the whole room organized. The recon soldiers and the walkie talkies, the moving buddies, the meetings — this is a smooth-running team. A lot of this is due to writers and creators wanting to showcase toys from their youth. The movie is fun! It works, though, because Woody’s character traits are so integrated into the gimmick.
Is he a Three? He’s so beloved, in Andy’s room but also as a collectible. The cowboy doll is a cool toy. What happens when all the success and ease of a Three’s world is upended by chance? Buzz wishes him no harm and is not the villain. He’s just a random event that wrecks Woody’s comfort.
I want to say, though, that Woody’s a Four. His emotional intensity, his dependence on the love from the room, his connection to Andy. His battle with Sid seems particularly Four-ish. He’s able to gain the sympathy of Sid’s toys, even when Andy’s toys have rejected him. The journey through emotion Woody makes seems like a Four path.
Also, and this is funny, Woody moves like a Four. He’s tall, gangly, with long arms and legs. Remember his run? Doesn’t it make you laugh when you imagine him as a Four? Woody was drawn/modeled by people who knew his character. This isn’t just a process of casting an actor who may or may not match the Enneagram of their role. Something made the creators design a Woody that fits certain physical parameters. I like this mysterious sense of synergy!