The Legend of Frosty the Snowman is a 2005 direct-to-video DVD animated film that serves as a sequel/ prequel to Frosty the Snowman.
But Tommy however doesn't accept Frosty's invitation to play outside in the snow, because he’s afraid of disappointing his father (ever since he fail one time in school). So Frosty instead befriends with his best friend/ next-door neighbor, Walter Wader, who shocks everyone, especially his very strict mother; Mrs. Wader, by breaking curfew and flying, sledding, snowball-fighting and "having fun" with Frosty in the Evergreen woods.
Walter's rule-breaking gets all the other kids of Evergreen talking, but it greatly upsets Principal Pankley, who is even more adamantly opposed to magic than Mayor Tinkerton. Pankley uses the arrival of Frosty to sow doubts among the townspeople about the Mayor's leadership, and little by little he begins to take over the town. But once magic is stirred up, it is not easily contained.
Everything changes, though, when Tommy finds a secret room beneath the Evergreen 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 father (which is Mayor Tinkerton) met Frosty when he was a boy, and did believe in magic once upon a time; and that Pankley, a childhood friend of his father's, took Frosty's hat and hid it away in an attic (which is the same attic from the beginning of the movie), causing young Mayor Tinkerton to lose his faith in magic.
Meanwhile, Frosty joyfully wins over the kids, including Tommy's love interest; Sara Simple (a sharp, independent young girl who tells her mother, "I don't want to be a princess- I want to be an urban planner"), his older brother; Charlie Tinkerton; and even Simon, Sully, and Sonny Sklarow. Frosty befriends each of them through the simple means of believing in them, which inspires them to begin to believe in themselves one by one.
Increasingly desperate to deny the existence of Frosty and keep Evergreen fun-free, Pankley tricks Walter into helping him lure Frosty for some ice-skating fun in the woods, then tricks Frosty into venturing him onto "thin ice". But before Walter, noticing the thin ice begin cracking, can be able to save his friend, the unnoticed Frosty falls through the ice after it cracked and melts, and Pankley was be able to capture his hat, which is the key to his magic. This incident makes Walter sob in tears.
As all of this unfolds, Tommy, who was the first one to whom Frosty appeared, has been sitting on the sidelines in gym class, watching his best friend, his brother, and his hoped-for sweetheart 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 father would disapprove of him acknowledging the existence of magic). The comic book also reveals to Tommy what Pankley has just done (with Walter's unwitting help) to recapture Frosty.
All this time, Tommy has held back from befriending Frosty out of loyalty to his father, who has always told Tommy not to believe in magic. But now Tommy sees that his father believed in magic one time, 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 father rediscover that magic is indeed real.
Tommy explains what's really going on to Charlie, Sara, Walter and the Sklarow brothers, and leads a daring rescue of Frosty and his hat in which Tommy and his companions help out. A climactic series of scenes follows in which Pankley tries and fails to recapture the hat, then tries to deter the townspeople (including Mayor Tinkerton) from going into the woods to see what all the ruckus and noise are about. The parents are angry, worried and confused: why are their kids out at night? And can this magical snowman they have been hearing about be real after all?
Meanwhile, Mayor Tinkerton refuses to be deterred, and Tommy is able to reintroduce his father to the old friend, who Mayor Tinkerton had long since stopped believing in ever since. Pankley tries to stir them up to regain control of the situation, but Walter however breaks the spell by throwing a snowball at Pankley. And one by one, the other kids--including Tommy and their parents join in, until all the citizens of Evergreen, which had forgotten how to have fun, gives itself over joyously to a "snowball-fighting, horseplaying, lark of a good time."
A brief epilogue shows the audience Evergreen transformed into spring—with Charlie playing football, Tommy skateboarding, Mayor Tinkerton doing magic tricks (in honor of his father; Professor Hinkle), and Sara reading a book about urban planning, even when she glazed to Tommy into her eyes.
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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