The first three Toy Story films center on Woody's relationship with his kid, Andy. But while Andy was born in 1989, Toy Story 2 and Toy Story 4 both point out that Woody is a collectible toy from the 1950's. What was Woody's life like for the 40 years before he met Andy?
The movies do not explicitly state the years in which they take place, which makes the Toy Story film timeline inexact. However, references within the films can date the first movie as taking place in 1995. This means that Andy, who is turning six in the first film, was born in 1989. Woody and Andy were friends from an early age, so Woody and Andy could have first met when Andy was a baby.
Even then, however, Woody is a lot older than Andy. In Toy Story 2, Woody learns that he is a collectible toy based on the 1950s television show Woody's Roundup. Along with Jessie the Cowgirl, Bullseye the Horse, and Stinky Pete the Prospector, Woody is part of a limited edition set of toys that are rare enough to be sold to a Japanese museum. The black-and-white aesthetic always suggested the 50s, and this is confirmed in Toy Story 4 by Gabby Gabby. As a result, Woody would have lived thirty to forty years of his life before meeting Andy.
When Al tries to buy Woody at the yard sale in Toy Story 2, Andy's mother apologizes and takes Woody back, saying that he is "an old family toy." Andy is only around eight years old in Toy Story 2, and as his mother identifies Woody as a family toy, rather than her son's toy, that seems to signal that Woody has been in the family's possession longer than Andy has been alive.
In Toy Story 2, Woody remarks, "A record player! I haven't seen one of these in ages." It's unlikely that Andy would have had a record player in the 1990s, so this would indicate that Woody does have memories of his life before. It's likely that Woody was owned by one of Andy's parents when they were children. Some fan theories go deep into Andy's missing father, and hinge on the idea that Woody once belonged to him; because Andy associates Woody with his father, he is all the more attached to the toy.
The difference between his previous owner(s) and Andy is that Woody was Andy's favorite toy, and the connection that they shared was special. In Toy Story 4, it's the one that defines Woody's entire existence. Even though Woody's time with Andy was relatively short, Andy was the kid that was most important to Woody.
