Top 10 Saddest Toy Story Moments

#10: Woody Is Ready To Stay Behind “Toy Story 2” (1999)

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Nothing in the world matters more to Woody than Andy. The toy will do nearly anything to be by his owner’s side, but, as a sheriff, Woody is also a symbol of honor and justice. After being captured by a collector named Al, Woody meets Jessie, Bullseye, and Stinky Pete. Woody learns that he, along with these three other toys, is a part of a collection which Al intends to sell to a museum. While he initially intends to return to Andy, Woody learns that, if he leaves, the other toys will be left in storage. When Woody is presented with the choice to pick between his happiness and that of others, the cowboy is willing to make the sacrifice.

A constant theme throughout the “Toy Story” franchise is that change is inevitable. In "Toy Story 3.", Andy is preparing to head out to college. While Woody and the gang have been shelved for years, there remains a flicker of hope that Andy may play with the toys one last time; unfortunately, things don't pan out that way. This moment makes it abundantly clear that the good old days are truly over and Andy has moved on. The toys that once meant so much to Andy are now just remnants from the past.

Villains with tragic backstories are hardly anything new for the "Toy Story" franchise. Despite initially giving some horror villains a run for their money, we learn that there’s more than meets the eye with “Toy Story 4”’s Gabby Gabby, a doll who will do whatever it takes to obtain a new voice box. It is later revealed that her motive behind this was to convince a young girl named Harmony to adopt her. Unfortunately, even with Woody's voice box, Harmony barely gives the talking doll the time of day. Gabby's fear of being forever alone is overwhelming and relatable; luckily, love happens to only be a carnival away.

Villains in "Toy Story" villains can be downright intimidating, and Lots-O'-Huggin' Bear was no exception. The toy bear ruled Sunnyside Daycare with an iron paw and sought to make everyone as miserable as possible. So, such a detestable character would need a pretty heartbreaking backstory to garner any sympathy. Once kindhearted and considerate, Lotso’s heart darkened beyond the point of no return when he was mistakenly abandoned and replaced. In all fairness, Lotso probably could have handled the rejection better, but that does not make his backstory any less sad.

#6: Woody & Bo Peep Say Goodbye “Toy Story 4” (2019)

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"Toy Story 4" begins by explaining Bo Peep's absence in the third entry, subtly signalling viewers to get their tissues ready. Being that it's a toy meant for younger children, Bo Peep was outgrown rather quickly by Molly, who donated the porcelain figurine shortly after the events of "Toy Story 2." If being discarded by the most important person in her life was not already sad enough, Bo Peep also had to say goodbye to Woody, the most important toy in her life. We know Woody would do almost anything for Bo Peep, which makes the moment all the more sad.

#5: Buzz Flies No More “Toy Story” (1995)

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Buzz Lightyear's big arc in the original film is one of self-acceptance, as the Space Ranger has to come to terms with the fact he is only a toy. Although Buzz's delusion produces comedy gold, the moments when the ranger sees his toyline's commercial, along with his failing attempts to fly, are anything but funny. Even if everyone else knew the truth, Buzz's self-identity is shattered by this revelation and, despite knowing that failure is the only viable outcome, it's not hard for viewers to wish for Buzz to defy expectations and find a way to fly.

#4: The Incinerator “Toy Story 3” (2010)

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Remember that time when "Toy Story's" beloved cast was about to literally go down in flames? Yeah, Pixar almost went there. After being betrayed by Lotso, Woody and the gang are dropped into the furnace and come face to face with death. As escape seems impossible, the toys decide to go out together as a family and hold hands. Even if it’s unlikely that Pixar would follow through with cooking these iconic characters alive, the moment still delivers a powerful kick to the heart and showcases the strong bond shared between the toys.

With Andy no longer around, Woody enters a period of prolonged mourning and struggles to fit in as one of Bonnie's toys. Although a reunion with Bo Peep helps snap the cowboy out of his funk, it also forces Woody to pick between staying with Buzz and the gang, or starting a new life with the figurine. These toys have been through a lot together over the years, so Woody's decision to stay with Bo Peep was a hard pill to swallow. While their roads may diverge, the toys’ friendships are everlasting.

#2: When She Loved Me “Toy Story 2” (1999)

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If there’s something "Toy Story" always knocks out of the park, it’s devastating backstories. Earnest and lively, Jessie is a ray of sunshine and positivity, traits made even more admirable once it is revealed how the yodeling cowgirl ended up all by herself. Jessie was once owned by Emily, a girl who loved playing with the cowgirl, at least, until the child grew up and lost interest. Accompanied by the haunting "When She Loved Me" song, Jessie's sobering tone makes this moment all the more heartbreaking. However, Emily isn't an exception, as all kids eventually outgrow their toys.

#1: The Toys Say Goodbye to Andy “Toy Story 3” (2010)

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Built-up throughout the entirety of "Toy Story 3," the moment Andy finally moves on of the toys is inevitable. After a long struggle to make their way back to Andy, the toys are rewarded with one final play session with their owner before being handed over to Bonnie. Andy's hesitation to give away Woody is especially moving, as it's only natural for someone to want to hold onto an important piece of their childhood. This scene is the ultimate passing of the torch moment, one that represents the end of a chapter and also the start of something new for both the toys and Andy.