History NightmareFuel / ThePhantomTollbooth

* The physical map of the Land Beyond displays the Mountains of Ignorance as grotesque faces, hinting at the nightmarish creatures long before they appear*

Despite being a whimsical story about a boy learning the importance of learning accompanied by the suave and energetic animation of [[Creator/ChuckJones Chuck Jones]], it is filled with dark elements that manage to be even more disturbing than the book's already grim ideas and Jones is willing to go into much more terrifying designs for the villains than his usual comedic brand of characters.

** After the Trivium dies, the Demons get fed up and decide to gather together to form the personification of all Ignorance, a bluish-purple leonine-draconic hybrid [[MadeOfEvil made from the various demons of the worst evils of man]] [[FusionDance combining together]] into the thing they all spring from: '''HATE.'' In it's brief appearance, it [[HeroKiller temporarily kills Tock]] and it would've smashed Milo and the Humbug as well, had Milo not used his trump card to kill it.

* The Demons of Ignorance [[NonStandardCharacterDesign drawn in a very rough style compared to the lightly drawn cast, and many look very disturbing]]. The prime example is the (nonspeaking) Two-Faced Hypocrite, which looks like a two-headed dragon straight out of Hell. Even worse is the personification of all Ignorance, a bluish-purple leonine-draconic hybrid [[MadeOfEvil made from the various demons of the worst evils of man]] [[FusionDance combining together]] into the thing they all spring from: '''HATE.'''

** The Terrible Trivium, a being [[TheBlank with no visual face]] and in the movie, is essentially an animated suit given form with his head being the only indication of his humanoid nature, but his intent is what makes him a special kind of unnerving compared to the others. [[FauxAffablyEvil His seemingly polite nature to convince others to do menial tasks]] is accented with the capacity of suddenly gaining sinister indications of eyebrows and his slow approach to the heroes with a twinkling flash in the indication of where his eye should be during his BadassBoast implies [[NothingIsScarier he was going to do something terrible to them before Tock frightens him off]].

** The Horrible Hopping Hindsight who has legs arched backward, with [[EyePop pink eyes in a perpetual elongated outside the socket]] while breathing fire, looking like something retroactively out of a Rob Zombie album cover than a simple children's story.

** The Terrible Trivium, his FauxAffablyEvil nature is accented with the capacity of suddenly gaining sinister indications of eyebrows and his slow approach to the heroes during his BadassBoast implies [[NothingIsScarier he was going to do something terrible to them before Tock frightens him off]].

** The soundtrack while very whimsical at times, always has an undertone of menace until the conflict is resolved, hinting at the darker elements of the story that become clearer by the time they reach the Mountain of Ignorance.
** Before the adventure even begins, Milo is confronted by a stark red and white striped box that clashes with his realistically muted room and it comes to life in as elements pop into existence in an instant as the boy is understandably freaked out.

** The physical map of the Land Beyond displays the Mountains of Ignorance as grotesque faces, hinting at the nightmarish creatures long before they appear*
* Officer Short Shrift, [[AmbiguouslyHuman a vaguely human-like police officer who has a single wheel with an extending lever as a leg and a visor that completely obscures his eyes, which are only revealed when he takes on the role of an executioner, but also his face]]. He also has a habit of delivering disproportionate jail sentences of millions of years for the most menial offenses.
* The Doldrums, while not seemingly menacing, being a dreary place embodying the lack of will to do anything made of sludge and populated by the Lethargians. a race of lazy, yellow-eyed creatures made of a grayish, semi-transparent liquid-like substance that causes these race's individuals to combine and separate into copies or the same being, only having the interest of being lazy, but if on closer examination, their goals have insidious purposes of robbing one of complete agency until one dies or is assimilated into them as a dangerous alternative. In a land in which thinking and breathing itself are outlawed, the very swamp comes alive to chase you, and if that's not bad enough, the personifications of Boredom, Sloth, and Lethargy will deliberately do their best to keep you where you are [[FauxAffablyEvil hiding their truly malign intentions under a relaxed and casual facade]]. A particularly sinister moment comes when the laidback facade drops mid-song and the Lethargians start shooting devilishly triumphant looks at each other as their trap does its work on Milo. [[VoiceOfTheLegion They also have a habit of having a distorted reverb to their voice as if the sound is slowly catching up to the words]], which make them even eerier.
** And it’s frighteningly easy to be directed there. If one ever loses focus for a moment, they are pulled into the realm and into the trap of the Lethargians. Milo heavily implied to be one of countless victims.

* The Doldrums, while not seemingly menacing, being a dreary place embodying the lack of will to do anything made of sludge and populated by the Lethargians. a race of lazy creatures made of a yellow-eyed, grayish liquid-like substance that causes these race's individuals to combine and separate into copies or the same being, only having the interest of being lazy, but if on closer examination, their goals have insidious purposes of robbing one of complete agency until one dies or is assimilated into them as a dangerous alternative. In a land in which thinking and breathing itself are outlawed, the very swamp comes alive to chase you, and if that's not bad enough, the personifications of Boredom, Sloth, and Lethargy will deliberately do their best to keep you where you are [[FauxAffablyEvil hiding their truly malign intentions under a relaxed and casual facade]]. A particularly sinister moment comes when the laidback facade drops mid-song and the Lethargians start shooting devilishly triumphant looks at each other as their trap does its work on Milo. [[VoiceOfTheLegion They also have a habit of having a distorted reverb to their voice as if the sound is slowly catching up to the words]], which make them even eerier.

* The Doldrums, while not seemingly menacing, being lazy creatures made of a grayish liquid-like substance that causes these race's individuals to combine and separate, only having the interest of being lazy, but if on closer examination, their goals have insidious purposes of robbing one of complete agency until one dies or is assimilated into them as a dangerous alternative. In a land in which thinking and breathing itself are outlawed, the very swamp comes alive to chase you, and if that's not bad enough, the personifications of Boredom, Sloth, and Lethargy will deliberately do their best to keep you where you are [[FauxAffablyEvil hiding their truly malign intentions under a relaxed and casual facade]]. A particularly sinister moment comes when the laidback facade drops mid-song and the Lethargians start shooting devilishly triumphant looks at each other as their trap does its work on Milo.

** The Doldrums, while not seemingly menacing, being lazy creatures made of a grayish liquid-like substance that causes these race's individuals to combine and separate, only having the interest of being lazy, but if on closer examination, their goals have insidious purposes of robbing one of complete agency until one dies or is assimilated into them as a dangerous alternative. In a land in which thinking and breathing itself are outlawed, the very swamp comes alive to chase you, and if that's not bad enough, the personifications of Boredom, Sloth, and Lethargy will deliberately do their best to keep you where you are [[FauxAffablyEvil hiding their truly malign intentions under a relaxed and casual facade]]. A particularly sinister moment comes when the laidback facade drops mid-song and the Lethargians start shooting devilishly triumphant looks at each other as their trap does its work on Milo.
** The Demons of Ignorance [[NonStandardCharacterDesign drawn in a very rough style compared to the lightly drawn cast, and many look very disturbing]]. The prime example is the (nonspeaking) Two-Faced Hypocrite, which looks like a two-headed dragon straight out of Hell. Even worse is the personification of all Ignorance, a bluish-purple leonine-draconic hybrid [[MadeOfEvil made from the various demons of the worst evils of man]] [[FusionDance combining together]] into the thing they all spring from: '''HATE.'''

** The physical map of the Land Beyond displays the Mountains of Ignorance as grotesque faces, hinting at the nightmarish creatures long before they appear.
* Officer Short Shrift, [[AmbiguouslyHuman a vaguely human-like police officer who has a single wheel with an extending lever as a leg and a visor that completely obscures his eyes, which are only revealed when he takes on the role of an executioner, but also his face]]. He also has a habit of delivering disproportionate jail sentences of millions of years for the most menial offenses.
** The Doldrums are absolutely terrifying from one point of view. In a land in which thinking and breathing itself are outlawed, the very swamp comes alive to chase you, and if that's not bad enough, the personifications of Boredom, Sloth, and Lethargy will deliberately do their best to keep you where you are [[FauxAffablyEvil hiding their truly malign intentions under a relaxed and casual facade]]. A particularly sinister moment comes when the laidback facade drops mid-song and the Lethargians start shooting devilishly triumphant looks at each other as their trap does its work on Milo.

** The physical map of the Land Beyond displays the Mountains of Ignorance as grotesque faces, hinting to the nightmarish creatures long before they appear.
** The Doldrums are absolutely terrifying from one point of view. In a land in which thinking and breathing itself are outlawed, the very swamp comes alive to chase you, and if that's not bad enough, the personifications of Boredom, Sloth, and Lethargy will deliberately do their best to keep you where you are [[FauxAffablyEvil hiding their truly malign intentions under a relaxed and casual facade]]. A particularly sinister moment comes when the facade drops mid-song and the Lethargians start shooting devilishly triumphant looks at each other as their trap does its work on Milo.