There is no arguing that the original Toy Story rewrote the rulebook. It was a giant leap forward in 3D animation, matched by a sophistication of storytelling and humour that came right alongside it. To me, that only makes it more remarkable that, against every expectation, Toy Story 2 manages to better it on every single front. The temptation of a sequel, to go bigger, bolder and darker, can easily turn into a trap, yet Woody and Buzz's second adventure carries it off so smoothly that it never looks like effort. It is a precise expansion of everything audiences adored about Toy Story, with several of its own unforgettable moments thrown in for good measure.
A sequel that remembers the lessons of the greats
Tellingly, Toy Story 2 keeps nodding towards The Empire Strikes Back, the definitive bigger-bolder-darker sequel. It parodies that film's most famous twist within the Buzz-versus-Zurg storyline, while also grasping exactly what allowed Empire to surpass the original Star Wars. Just as Empire did, Toy Story 2 challenges its heroes at a deep level, pulling the toys apart as they work out their futures. It introduces new characters you simply cannot picture being absent from the Toy Story mythos, and it widens the world enormously, carrying these inherently domestic characters well beyond Andy's neighbourhood.
The childhood favourite that felt enormous
As a kid, this was the one I rewound most often on VHS. I loved the first film, but the second felt massive. That brilliant opening sequence set inside the Buzz Lightyear video game, stretching the series' idea of what it means to play, was a tantalising taste of the sci-fi spectacles waiting for me in the years ahead. The runaway-plane finale was heart-in-mouth thrilling. The aisles of Al's Toy Barn were stuffed with gags (the Barbie sequence plants the seed of what Greta Gerwig's outstanding film would later become), while also showing just how vast the world of toys really was. And, of course, it gave us Jessie, Bullseye and the whole Woody's Roundup gang.
Toy Story 2 is a prism through which to refract Woody's past, present, and divergent possible futures.
The side of Woody he never knew existed
You cannot imagine Toy Story now without Woody's old TV companions, and their introduction here is a stroke of genius. We had already met Woody as the sheriff of Andy's toys, a firm believer in the little family of playthings gathered by their cherished kid owner. So what is the one thing that could plausibly rattle that belief? A different family Woody never knew he had, another gang of which he is also the figurehead. Jessie and Bullseye unlock a whole side of him, an entire history, that he had never connected with. And they need him. The film so convincingly builds a world in which the ever-reliable Woody might leave Andy behind for something else. He is more than a beloved toy. He is a pop-cultural icon, a vintage collectible, the rootin'-est tootin'-est cowboy in the Wild Wild West.
The peak version of everyone we love
Toy Story 2 does not merely burrow under the (plastic) skin of our favourite characters, it hands us their finest versions. The original Toy Story is spikier than you remember, hinging on the tension between Woody's insecurities and Buzz's sci-fi delusions. But Toy Story 2 gives us the Woody-Buzz dynamic we truly love and recall, two best friends who would do anything for each other. It is a clever reversal of the first film to have Buzz risk everything this time, trying to bring Woody home. His ragtag crew of Rex, Slinky, Hamm and Mr. Potato Head venturing across town, triggering traffic pile-ups and toy-shop carnage along the way, is the film's funniest strand.
The quiet terror of becoming obsolete
That was the stuff I loved most as a child. As an adult, it is the emotional flip-side that impresses me most. The fear of obsolescence has always sat at the heart of Toy Story, and Toy Story 2 digs far deeper into it. Woody is physically torn in the opening act, mirroring a similar psychological tearing. Missing out on Cowboy Camp with Andy marks the first time he has genuinely been left behind, and it will not be the last. Eventually, Andy will no longer need him. The film truly prises open Toy Story's biggest philosophical question: what is the purpose of a toy who is no longer played with?
Jessie's heartbreak and an unforgettable song
That question is explored in heartbreaking, truly devastating fashion through Jessie's backstory. Her Andy was 'Emily', a girl who loved ponies and cowgirls, and therefore Jessie. Until she came to prefer lipstick and sleepovers, all the things children should grow into, leaving Jessie forgotten beneath the bed. It is crushing. Yet there is no villain in this story. It would be stranger still if Emily had kept playing with Jessie into her teens. Toy Story 2 does not try to solve this, it makes room for that sadness, for the natural end of things, and lets the heroes grapple with what comes next. That sequence, alongside the eerily mesmeric Woody repair scene, is the film's crowning glory, achingly bittersweet and beautifully scored by Sarah McLachlan's heart-stomping ballad 'When She Loved Me'.
It's the tightest and funniest of the bunch, with the best versions of these characters.
The villains carrying their own wound
This gaping emotional wound is central to the motivations of the film's supposed villains, Al, the Chicken Man of Al's Toy Barn and an adult toy collector, and the Woody's Roundup prospector Stinky Pete. (As a grown-up with plenty of toys in his office, I hate the thought that I might be Al now. I like to hope my Godzilla and Star Wars figures are all friends the moment I leave the room, and I promise none of them are sealed in their boxes.) Al obliviously denies the toys the very thing that gives them purpose, actually being played with, while Stinky Pete never moved past the fact that he stayed unopened. The old prospector makes a persuasive case: Woody will inevitably be forgotten one day, so why not embrace becoming a museum exhibit?
The right choice and the soul of the series
Of course, once Buzz and company arrive, Woody finally makes the right call. He will go back to Andy and take the other Roundup folks along for a few more years of play. They will sort out the rest later. It is an outcome that justifies the entire remainder of the Toy Story saga, right through to the new fifth film and beyond: these toys, and these films, exist to be played with by multiple generations. They should not be boxed away forever, preserved in amber as idols to be worshipped.
While I admire Toy Story 3's heavyweight ending and love every film in the series, Toy Story 2 will always be my go-to. It is not just the comfort of a childhood favourite, it is the tightest and funniest of the lot, with the best versions of these characters, all capped off by a 'blooper' reel for the ages. Ride like the wind!
Toy Story 2 is currently streaming on Disney+.
