The Legend of Frosty the Snowman is a 2005 direct-to-video DVD animated-buddy-comedy film that serves as a sequel/ prequel to Frosty the Snowman.
First narrated and sung by the screenwriter; Evan Gore, but now lent to Burt Reynolds and a veteran actor/voice artist Bill Fagerbakke in the role of Frosty (ever since Nickelodeon's Patrick the Snowman, and would provide his voice himself), this new chapter in the saga revisits Frosty many years after he shouts out his first original catchphrase, "Happy Birthday!", when he first appears in a town of Evergreen where magic, silliness, and nonsense of all kinds are strictly against the rules.
At the beginning of the story, we see the picture perfect town of Evergreen, where all the local children are bound to a ridiculously strict curfew and not allowed to have any kind of fun whatsoever. One calm boy living in that town is named Tommy Tinkerton (the film's tritagonist), the son of the town’s impossibly upbeat but no-nonsense mayor (voiced by Tom Kenny). Another storyline stars Tommy’s best friend, Walter Wader (the main protagonist of the story), who shocks everyone, especially his very strict mother, befriends a snowman named Frosty and have fun in the woods. Walter’s rule-breaking gets all the kids of Evergreen talking, but it greatly upsets Principal Pankley (the story's main antagonist), who is even more adamantly opposed to magic than Mr. Tinkerton (who betrays Tommy that he is under Pankley's control after Walter tells the truth to Mr. Tinkerton). Principal Pankley uses the arrival of Frosty to sow doubts among the townspeople about Mayor Tinkerton’s leadership, and little by little he begins to take over the town.
But once magic is stirred up, it isn’t easily contained. One by one, Frosty wins over the other kids of Evergreen, including Tommy's older bullying brother, Charlie Tinkerton, who teases his brother, Tommy's lonely love interest, Sara Simple (a sharp and independent girl who wants to be an urban planner instead of a "princess"); and the happy-go-lucky triplets, Sonny, Sully, and Simon Sklarow. Frosty befriends each of them through the simple means of believing in them, which inspires them to begin to believe in themselves. Increasingly desperate to deny the existence of Frosty and keep Evergreen fun-free, Principal Pankley tricks Walter Wader into helping him lure Frosty for some ice-skating fun, then tricks Frosty into venturing onto thin ice. Before Walter can save his friend, Frosty, realizing it's too late to escape, falls through the ice and melts, and Principal Pankley captures Frosty’s hat, which is the key to his magic.
As all of this unfolds, Tommy Tinkerton, who was the first one to whom Frosty appeared, has been sitting on the sidelines, watching his best friend, his brother, and his love interest experiencing adventure and magic in which he could share. But he has held back, even though he yearns to meet Frosty, out of loyalty to his dad (because he knows his dad would disapprove of him acknowledging the existence of magic). Everything changes, though, when Tommy finds a secret room beneath the library, in which he discovers a comic book filled with secrets about Frosty.
At first, most of the comic book is blank. Each time Tommy checks it again, new panels appear. Over the course of several scenes, Tommy learns that Frosty’s magic is in his hat; that his dad (Mr. Tinkerton) met Frosty when he was a boy, and did believe in magic once upon a time; and that Principal Pankley, a childhood friend of his father’s, took Frosty’s hat and hid it away in an attic (the same attic from which the hat escaped at the beginning of the story), causing young Mr. Tinkerton to lose his faith in magic. The comic book also reveals to Tommy what Principal Pankley has just done (with Walter Wader’s unwitting help) to recapture Frosty.
All this time, Tommy has held back from befriending Frosty out of loyalty to his dad, who has always told Tommy not to believe in magic. But now Tommy sees that his dad once believed in magic, too, but was tricked into losing faith. And Tommy realizes that the most loyal thing he can do is not to hide from magic, but to help his dad rediscover that magic is indeed real. Tommy explains what’s really going on to a now-reformed Charlie, Sara, Walter, and the Sklarow triplets, and leads a daring rescue of Frosty’s hat in which all the kids help out. A final battle between Principal Pankley, Walter, Tommy, Charlie, Sara and the Sklarow triplets playing capture the flag with the hat as the flag features a climactic series of scenes follows in which Principal Pankley tries and fails to recapture the hat, then tries to deter the townspeople (including Mr. Tinkerton) from going into the woods to see what all the ruckus and noise are about. But Mr. Tinkerton refuses to be deterred, and Tommy is able to reintroduce his dad to the old friend, who Mr. Tinkerton had long since stopped believing in.
Meanwhile, the other parents are confused and angry: why are their kids out at night? And can this magical snowman they’ve been hearing about be real after all? Principal Pankley tries to stir them up to regain control of the situation, but Walter Wader breaks the spell by throwing a snowball at Principal Pankley. And one by one, the other kids and parents join in, until the town of Evergreen, which had forgotten how to have fun, gives itself over joyously to a “snowball-fighting, horseplaying, lark of a good time.”
As the snow melts, Frosty says goodbye to Evergreen and Pankley gets fired as principal and being arrested for banning magic, an epilogue shows us a Evergreen transformed into spring—with Mr. Tinkerton doing magic tricks, Charlie playing football, Tommy skateboarding, Sara reading a book about urban planning and Evergreen letting the parents take care of their children.
All the time, the story has been narrated (à la "Our Town") by a warm, wise, seemingly omniscient old man named Thomas who appears periodically and comments on the events unfolding in Evergreen. In the final scene, Thomas reveals that he is Tommy, all grown up and now married to Sara; and he has been telling the audience his own story.
Though advertised as a sequel to the classic Rankin/Bass special, The Legend of Frosty the Snowman holds only a loose continuity with it. The only connection between the two seems to be the magician (Professor Hinkle), Tommy's father; Mayor Tinkerton (whose name is revealed as "Theodore Tinkerton", also one of Karen's friends in the original special and apparently Hinkle's son), and the hat. Other than them and Frosty, no character appears in both stories, nor do the stories match up in details such as who first brought Frosty to life or what happened to him afterwards. Despite this, the film has more continuity with the original than does the show more commonly recognized as its sequel, Frosty Returns.
- Grey DeLisle - Miss Sharpey, Simon Sklarow, Sully Sklarow
- Jeannie Elias - Charlie Tinkerton, Librarian
- Bill Fagerbakke - Frosty
- Evan Gore - Paperboy
- David Jeremiah - Mr. Simple, Townsperson #1, Mr. Sklarow
- Tom Kenny - Mr. Tinkerton
- Tress MacNeille - Mrs. Simple, Girl #1
- Kenny Blank (also credited as Kenn Michael) - Walter Wader
- Larry Miller - Principal Pankley
- Candi Milo - Mrs. Tinkerton, Girl #2
- Burt Reynolds - The Narrator (a.k.a Thomas)
- Kath Soucie - Tommy Tinkerton, Adult Sara Simple
- Tara Strong - Sara Simple, Sonny Sklarow
- Vernee Watson-Johnson - Mrs. Wader
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