In this photo, you see Andy's cowboy hat that he plays with throughout his childhood. Study it closely.
Notice anything weird about the hat? It looks nothing like the hat worn by his favorite toy, Woody. Why wouldn't Andy wear a hat that was brown? Click the arrow to continue to the next slide.
We don't think about it because most of us are normal human beings with things like jobs and tax exemptions. But I want you to take a quick journey with me: Andy got this hat from his mom.
In Toy Story 2, young Andy Davis left for summer camp, and his mom held a yard sale. "The Chicken Man" found Woody in one of the boxes (he was trying to save a fellow toy) and pleaded with Ms. Davis to sell him because Woody is a collectible from the 1950s.
Ms. Davis refuses, acknowledging that Woody is "an old family toy." Not that much time has passed between the Toy Story movies, but we know that Andy has had Woody since Kindergarten, according to Mr. Potato Head. Andy's 6th birthday is in the first Toy Story, which makes him 7 or 8 in this movie. Woody doesn't seem all that old in comparison.
Further, Woody has no recollection of who he is. Many have suggested that this is because he was owned by Andy's father, who is never mentioned in the movies. Molly is a baby in the first movie, which means Andy's father either died or walked out not long before the movies started.
A reasonable assumption is that Andy's mom gave Woody, his father's toy, to him on his 5th birthday. After all, she gave him Buzz Lightyear on his next birthday. If Woody had been a new toy when Ms. Davis gave him to Andy, then he would know exactly who he is was, which is unlikely because he is so rare.