Since 1995, Pixar's Toy Story franchise has been a masterclass in blending humor with heartbreak. Unlike most sequels that diminish in quality, each new chapter has deepened our connection to Woody, Buzz, and the gang. With Toy Story 5 breaking box-office records, it's clear audiences can't get enough of these beloved characters—even when they leave us sobbing. Here's our ranking of every Toy Story movie by how much it will make you cry.
5. Toy Story (1995)
The original film introduced us to a world where toys have feelings, and that alone is a recipe for tears. Woody (Tom Hanks) faces his first taste of rejection when Andy gets a flashy new Buzz Lightyear (Tim Allen). Watching Woody struggle with jealousy and obsolescence is tough, but Buzz's existential crisis hits harder. He genuinely believes he's a space ranger, only to discover he's just a toy. That moment of shattered identity is both painful and poignant, setting the emotional tone for everything to come.
4. Toy Story 5 (2026)
Even without seeing the full film, Toy Story 5 has one of the saddest premises in the series. Technology—in the form of a smart tablet—threatens to replace the old-fashioned toys. But the real heartbreak comes from Bonnie, who is growing up and being teased for still playing with dolls. She rejects Jessie (Joan Cusack), sending the cowgirl back to her former owner Emily. A flashback to "When She Loved Me" and a lunchbox with the name "Jessie" on it will leave you reaching for tissues.
3. Toy Story 2 (1999)
This sequel doubles down on the theme of being forgotten. Jessie's backstory, set to Sarah McLachlan's "When She Loved Me," is a devastating montage of a toy loved and then abandoned. Meanwhile, Woody discovers Wheezy, a penguin with a broken squeaker, sitting alone on a dusty shelf for years. The film's climax, where Woody nearly says goodbye to Andy forever, is a bittersweet moment that tugs at the heartstrings even when you know he'll return.
2. Toy Story 4 (2019)
Many fans thought Toy Story 3 was the perfect ending, but Toy Story 4 proved there was more heart to mine. Forky (Tony Hale), a spork turned toy, struggles with his self-worth, believing he's just trash. Watching him learn his value is both tragic and uplifting. The real tearjerker, though, is Woody's farewell. He accepts that Bonnie no longer needs him and chooses to leave with Bo Peep. The silent hug with Buzz, followed by Buzz saying, "He's not lost, not anymore," is a gut punch that rivals any moment in the series.
1. Toy Story 3 (2010)
Unsurprisingly, Toy Story 3 takes the top spot. The film delivers a double emotional wallop. First, the incinerator scene: the toys, facing certain death, join hands and accept their fate. It's a moment of pure love and sacrifice that leaves audiences in tears, even knowing they'll be saved. Then comes the ending, where Andy gives his toys to Bonnie and plays with them one last time. It's a perfect, heartbreaking conclusion to a story about growing up and letting go. For more on how storytelling can evoke such powerful emotions, check out our ranking of the most perfect anime of the last five years.
From Woody's jealousy to Bonnie's goodbye, the Toy Story movies remind us that love and loss are part of every journey. Which one makes you cry the hardest?
