Released in 1949, The Adventures of Ichabod and Mr. Toad is the 11th film in the Disney Animated Canon, and the last of the six (or seven if you count Fantasia) "package films" created by the studio in the '40s. Like Fun and Fancy Free, it is a collection of two short movies, bundled together to make one feature length movie. Despite the name, the two title characters' stories are actually presented in the reverse order:
The Adventures of Mr. Toad or The Wind in the Willows: Narrated by Basil Rathbone, it stars J. Thaddeus Toad (voiced by Eric Blore), owner of the fabulous Toad Hall. His various obsessions combined with his reckless personality causes a large amount of damage to the town, and thus has acquired a large amount of debt. His latest obsession, motor cars, gets him into trouble with the law. Sent to jail for stealing a car, he breaks free and sets out to clear his name.
The Story of Ichabod Crane or The Legend of Sleepy Hollow: Narrated by Bing Crosby, it stars the lanky Ichabod Crane (also voiced, like most of the male characters, by Crosby), a newcomer to the small town of Sleepy Hollow as their new schoolmaster. He becomes smitten with the richest woman in town, and competes with the local men for her affections, but soon finds himself facing off with the Headless Horseman one Halloween night.
Unlike most other Disney animated features from before the age of home video, this was never given a theatrical re-release. The two shorts are seen apart in individual collections more often than they are together in their original package film form.
Anti-Villain: Sleepy Hollow goes out of its way to prove that Brom Bones, while he's not above terrorizing the local schoolmaster to drive him out of town or bullying Katrina's other suitors, isn't really bad (just a bit of a Jerkass), and may in fact be a better husband for Katrina (unlike Ichabod, who appears to care more about her money.)
Ascended Extra: Cyril Proudbottom. Toad did have a horse in the original book, but he was an extremely minor character and only appeared briefly. Here, Cyril is Toad's loyal Sidekick.
Regardless of his fate, Ichabod Crane kind of deserved his encounter with the Headless Horseman. It's made abundantly clear that despite the girls (especially the main rich girl) fixating on him, all he's really after is money and free food. He even has a fantasy about marrying the rich girl and waiting for her old man to croak so he can inherit his vast fortune. With that in mind, do you really feel sorry for him by the end?
Toad is such a maniacal, irresponsible wack-a-doo that even his close friends think he stole the motor car.
"Well, guv'nor, you tried to sell me a stolen motor car!"
Butt Monkey: Brom Bones. The man would honestly not be all that out of place as the bad guy in a Bugs Bunny cartoon.
Cannot Cross Running Water: Brom Bones claims this about the Headless Horseman. Ichabod manages to cross the river and turns to see if the Horseman can follow him, he doesn't, but he does throw his pumpkin head at Ichabod.
Downer Ending: Sort of. The Story of Ichabod Crane lets the viewer decide if Ichabod simply moved away from Sleepy Hollow or was actually "spirited away" by the Headless Horseman.
It's very debatable how much of a downer this is regardless whether or not Ichabod actually dies or just gets scared out of town. For some, mostly kids, Ichabod comes across as an innocent victim who's just trying to get the girl. But for others, he's a selfish bastard trying to get the money from a rich girl's father through marriage, which is in fact very accurate to the original story.
The Dreaded: The Headless Horseman. According to Brom Bones' song even the demons themselves are afraid of him.
Establishing Character Moment: Ichabod's is when he opens a gate for a woman balancing a heavy load of pies — and then reveals he snuck a pie away for himself (as well as his ability to avoid all superstitious items without once looking up from his book.) Brom Bones, on the other hand, races like thunder through the village on a huge horse startling people, something that is greeted with laughs from his friends, carries in a big barrel of beer on his shoulders, pops it open to share with his buddies —then smashes open the top so the horses and dogs can drink too.
Evil Laugh: The Headless Horseman has one of the best ones in Disney history.
Fighting Your Friend: Not a very straight example, but Ratty's friendship with Toad briefly ends and he angrily refuses to help Toad when the police arrive at his house pounding on the door, (it turns out to actually be MacBadger, who has discovered Winky and his weasel gang in Toad Hall and now realized Toad was innocent) thinking he really did steal the motor car.
Toad: Hide me! Hide me Ratty! Ratty: Sorry Toad, but you owe a debt to society and you've got to pay! Mole, let them in.
Foreshadowing: When Ichabod Crane first walks through the streets of town, he deftly avoids walking under a ladder and uses his cane to steer a black cat away from his path. This establishes his superstitious nature early on, which Brom Bones uses later to his advantage.
Genki Girl: Tilda, the squat woman who takes a liking to Brome Bones and Ichabod.
Gold Digger: Ichabod seems to be more interested in the food of the women he courts than the women themselves. It's also directly stated that he only wants to marry Katrina for the money.
Grey and Gray Morality: The Sleepy Hollow segment, atypically for Disney, does not clearly define who is the bad guy and who the hero. Ichabod, the protagonist, is pretty clearly shown as a manipulative gold digger who only hesitates to beat his students in order to get into their mothers' good graces, whereas Brom Bones, the antagonist, has no stated amoral ulterior motives for wooing Katrina but is nevertheless something of a violent bully (he only firmly tips into the category of a "villain" if you interpret him as both being the Headless Horseman and having murdered Ichabod in the story's conclusion, neither of which is clearly spelled out by the film). Even Katrina herself comes across as somewhat morally questionable in the way she manipulates her suitors and seemingly enjoys and endorses the way Ichabod and Brom fight over her.
Toad: Afraid of the police? I? Toad? Afraid of the police? (laughs until a loud knock comes from the door) MacBadger: Open up! Open up I said! Toad:(horrorstruck) THE POLICE!
Ignored Aesop: While in prison, Toad realizes that he has been irresponsible and promises to never let his impulses get the better of him again. Unfortunately, once he escapes he reverts back to his usual self and the segment ends with him recklessly flying a plane.
Man Child: Moley is very innocent and childlike at times. As is Toad, though where Moley is more like a kind and gentle Cheerful Child, Toad's more of a hyperactive and unknowingly destructive kid with a number of personality disorders.
Maybe Magic, Maybe Mundane: The film is deliberately ambiguous as to whether or not the Headless Horseman exists, unlike the book, which very strongly hints that the horseman was Brom in disguise. Though Ichabod does look down the Horseman's coat at one point and doesn't appear to see anything.
Mood Whiplash: The "Ichabod" segment is essentially a wacky comedy...all the way up to the climax: one of the most terrifying sequences in Disney movie history, and unlike most of the other contenders, it's not followed up by a happy ending that cancels it out.
Never Found the Body: After his encounter with the Headless Horseman, all that can be found of Ichabod is his hat. There's a school of thought that believes Ichabod left Sleepy Hollow and married a widow. Of course, everyone knows what really happened...
Nothing Is Scarier: Before the Headless Horseman shows up, it's mostly silent though occasionally being abrupt to frighten the viewer, then it seems as if the wildlife is trying to warn him to just go back or beware, and then it seems like the Horseman actually is going to show up...but it turns out that it's just plants being knocked on wood. Ichabod and his horse laugh for a while, relieved...and then the Horseman shows up.
Another more true example - Ichabod actually gets a good look right at the Headless Horseman's missing head, and all he's greeted with is an evil laughter. The fact that the viewer is not shown what he saw really helps lead to the ambiguous ending.
Ominous Owl: During Ichabod's journey in the dark forest, there's a sinister-looking one perched on a tree. Though this could be Ichabod's imagination running wild.
Very much so in the Mr. Toad segment. It does avoid being an In Name Only adaptation by keeping Toad's personality the same as in the book (even if other characters are very different) and staying true to the basic story structure of the Toad parts of The Wind in the Willows, but it does change a few things up, attempting to turn Toad more sympathetic by having him actually innocent of the crime he's imprisoned for.
The Ichabod segment on the other hand is quite true to the original tale, both story and character wise. A few liberties were taken, but none that really change the story or characters of the story.
Run or Die: The Headless Horseman chase scene; Ichabod and his horse are clearly fleeing for their lives, even if they were never really in mortal peril.
Scooby-Doo Hoax: An example of one done right. Implied in the film, and more so in the original short story, Brom Bones apparently tells the story of the Headless Horseman, then dresses up as him to use Ichabod's established superstitious nature and the cover of night to scare the schoolmaster away.
Silent Protagonist: A rare animated example - Ichabod's vocalizations are limited to a few singing chords and screams - his thoughts are explained to the viewer by the narrator (although he does think to himself directly aloud when he imagines marrying Katrina and getting her money).
Slasher Smile: Brom Bones grins this way as he sings "The Headless Horseman", mainly to get Ichabod worked up.
Somewhere Song: Inverted early on in the Mr. Toad story, where he's "merrily on the road to nowhere in particular".
Spoiled Sweet: Despite charming suitors she has little interest in doing favors for her, Katrina is not without her kindness and does does not take well to Brom's bullying of her suitors. When Ichabod is knocked into a puddle he tried to help her cross, she tosses her handkerchief to him.
Stealth Pun: The prosecutor "interviewing" Angus MacBadger assumes he's answering "yes" to each loaded question, while Badger doesn't really get a chance to truly answer. He was "badgering" the witness, who IS a badger!
Stock Footage: The tussle for the deed to Toad Hall is the first use of the chase scene that was later seen in The Jungle Book, with Baloo as Mole and Mowgli as the deed, and Robin Hood, with the hen as Mole and a football as the deed.
Stuffy Brit: Ratty, of all animals, as a stark contrast to his more laid-back and easygoing book counterpart.
Wrongful Accusation Insurance: Breaks out of jail? Evades arrest? Steals a train? Apparently none of that matters because Toad didn't steal the car! Admittedly, it's one step up from the book where he actually did steal the car and still escaped with no repercussions, but still...