Toy Story 4 Theory: The Real Untold Tragedy Of Woody
2. Woody's Secret Past
When we meet Woody, he's driven by a sometimes crippling fear of toys being given away or lost or left behind. That's his role as leader of the toys and it's something he's particularly good at. When he meets up with Jessie, Stinky Pete and Bullseye in the first sequel, he befriends them easily not simply because they're from the same brand, but because he wants to "save" them from redundancy. Even in Toy Story 3, he's sympathetic to Lotso's broken mentality because he is a lost toy and that's Woody's weakness.
Looking a little deeper at what we know about Woody and his singular commitment to Andy, there's just no way he had an owner in those 40 years. If he had, he would bear either bear the wounds of repeated rejection and would talk about his previous kids or he would have come to realise that toys moving on is a fact of their existence. But he does neither.
Woody's entire arc from Toy Story to Toy Story 4, in fact, is learning that very revelation, because he's never been through it before.
The reality, sadly, is that Woody was just like Stinky Pete and Lotso for those 40 years. He never had an owner and he never had purpose. He was the lead toy from a show that was dropped before its finale because of a lack of interest. His show wasn't cancelled because the network were monsters and Stinky Pete didn't sit mint in the box because someone recognised his value as a collectible back in the 1950s - both were because nobody cared. Woody was a rejected toy from a redundant TV show and nobody wanted to love him until Andy came along.
That can be the only way Woody had no idea about Woody's Round-Up or how he belonged to a whole fandom back in the 1950s. He didn't experience any of it because he was never loved and never knew his part in a community of love. His reality was colder, more isolated and completely removed from everything he was designed to be.
That barren, devastating period is precisely why he's drawn to the broken, Frankenstein's monster toys in Sid's bedroom despite his fear. His experience is the whisper that makes him turn back to them. It's the same thing that ensures he'd later bring Jessie and Bullseye to Andy, despite the problems that new toys simply appearing out of nowhere could cause. It's the reason why he seems possible redemption in Stinky Pete, Big Baby, Lotso and Gabby Gabby. He knows what it means to be unloved and warped by isolation.
That's also why Woody is taken in by Stinky Pete in Toy Story 2 despite Andy still being young enough to want to play with him. Part of him knows what comes after Andy rejects him because he's been there before, so he's willing to entertain the idea of becoming a museum exhibit if it means he has a purpose.