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- Played by: Macaulay Culkin
- Adorkable: A very nervous but charming nerdy kid through and through.
- Badass Bookworm: Becomes this over the course of the film.
- Bookworm: But only of fact-based books, at first.
- Calling Card: His library card.
- Cowardly Lion: Easily frightened and cautious about everything, who overcomes his fears to become a better person.
- Everything Trying to Kill You: He believes everything is trying to hurt him in some shape or form. This becomes quite real in the animated world.
- False Crucible: It turns out everything that Richard went through was just a test by the Pagemaster. Needless to say, Richard does not take it very well.
- Genre Blindness: He apparently has read little-to-no literature in his life.
- Hypocritical Humor: When his father falls from the treehouse after Richard drops a bucket of nails on his head, Richard tells his father he cannot argue with statistics. Now who was it who dropped the bucket in the first place?
- Kid Hero: A contemporary take on the standard fantasy hero.
- Knight in Shining Armor: To battle the dragon.
- Logical Fallacies: Richard follows his life based on the statistics of how many accidents can occur in just about every scenario. As the main page points out, "8% of all household accidents involve ladders. Another 3% involve trees. We're looking at 11% probability here." First, Richard is ignoring some overlap between the 8% and the 3%. Secondly, he's assuming that an accident will happen, in which case the probability that it involves ladders is 8%, but that doesn't tell us anything about the chances that this specific ladder-climbing event will lead to an accident. What he needs is a statistic in the form of "X% of the time somebody climbs a ladder, they have an accident" rather than "X% of all accidents involve ladders."
- Ludicrous Precision: See Logical Fallacies above. In this case, of course, his precision is far more ludicrous than is average for this trope.
- Nerd Glasses: Round, brown spectacles.
- Trapped in Another World: After he slips, falls and gets knocked out.
- Took a Level in Badass: Enough to go up against a dragon to protect his new friends.
- Why Did It Have to Be Snakes?: His flaw is that he's afraid of pretty much everything.
- Played by: Christopher Lloyd
The title character and guardian of literature and reading. He sends Richard on his journey to find the exit, hoping he will overcome his fears. Possibly related to, or is, Mr. Dewey.
- Badass Bookworm: His clothes, his staff and even his beard all seem to be made out of pages.
- Badass Beard: A long white one that resembles book pages.
- Guile Hero: It's revealed that he deliberately sent Richard on his dangerous journey so he could conquer his phobias.
- Large Ham: Considering who voices him this is hardly surprising.
- Magic Staff: Shaped in the form of a scroll.
- Pet the Dog: Sends Richard back to his own world after Richard successfully overcomes his fears.
- Physical God: He's implied to be something like this in his world, judging by how the three books react to him.
- Robe and Wizard Hat: Stylised to resemble wrapped up paper.
- Secret Test of Character: His method to help Richard overcome his fears.
- What the Hell, Hero?: Richard gives him a grand chewing-out after realizing his entire ordeal was just the Pagemaster's test.
- Played by: Christopher Lloyd
- Badass Beard: Has a very distinctive pointed beard.
- Bookworm: This is clear based on his enthusiasm to give Richard a book.
- Informed Ability: "I have a talent at guessing what people need."
- Magical Library: In his eyes, the library is a magical place. It may or may not actually be magical, even though it seems Richard's adventures were All Just a Dream.
- Large Ham: What else would you expect from Christopher Lloyd?
- Meaningful Name: He's named after the Dewey Decimal System which is used to organize books in libraries.
- Scary Librarian: Subverted, since he only wants people to check out books.
- Secret Keeper: Seems to know what happened to Richard, but might actually be the Pagemaster. It's possible that he knows of the events that happen, thus why he allows Richard to take Horror, Adventure and Fantasy.
- Spooky Silent Library: No one seems to come to the library anymore.
- Played by: Patrick Stewart
- Affectionate Nickname: Calls Richard "Matey."
- Animate Inanimate Object: He's a talking book with arms and legs.
- Badass Boast: "I wrote the book on sailing. In fact, I am the book on sailing!"
- Butt-Monkey: Let's see—he is smashed by a book cart, falls off the top of a book shelf to the floor, drenched by a wive, looted by fellow pirates, tossed into a treasure chest during his only chance at a swordfight, enchanted to wear a dress and wig, and fried by a dragon.
- Earn Your Happy Ending: Follows Richard in the hopes of being checked out as a library book.
- Eyepatch of Power: Wears an eyepatch, although he still has both eyes intact. He wears it because it makes him look good.
- Forceful Kiss: Pulls this on Fantasy in a romantic moment and gets smacked for it.
- Genre Savvy: In the adventure section and horror section. Not so much in the fantasy section.
- Handicapped Badass: Has a hook and a peg leg, but is still pretty awesome.
- Hook Hand: He is a pirate after all.
- Jerk with a Heart of Gold: While he often argues with Fantasy and mocks Horror, he is a good man at heart and ultimately feels guilty for mistreating Horror.
- Large Ham: Well, he is a pirate and voiced by Patrick Stewart after all.
- Master Swordsman: Claims to be, but doesn't get much chance to show off his skills since he is the Butt-Monkey of the film.
- Ow, My Body Part!: "Oooh! Me binding!"
- Pirate: A very traditional role. Aside from being a talking book.
- Portal Book: Contains a number of pirate-related weaponry within his pages.
- Sensitive Guy and Manly Man: Adventure is the Manly Man to Horror's Sensitive Guy.
- Ship Tease: With Fantasy. They spend a good deal of the film bantering before he pulls a surprise kiss on her near the end. She doesn't take too kindly to that.
- Talk Like a Pirate: You'd better believe it, mateys.
- Ungrateful Bastard: Being the prideful braggard that he is, he certainly shows no gratitude when Horror and Fantasy help him and Richard fend off the pirates, especially since he spent the entire fight trapped in a chest right when he saw a good opportunity to have a good battle.Adventure: I coulda taken the lot of 'em with one hand tied behind me back! (storms off)Richard: It's just his way of saying thanks.Horror: (grabs a sword and puts on a bandana) You're welcome!
- Unusual Euphemism: To Fantasy: "How'd you like to curl up with a good book?"
- Played by: Whoopi Goldberg
- Animate Inanimate Object: A talking book with a fairy motif.
- Deadpan Snarker: Has her moments.Fantasy: (regarding Adventure) You know that short story?Richard: Yeah, he's Adventure.Fantasy: Honey, that's what they all say.Adventure: I heard that! I'll have you know I'm a classic!Fantasy: Mmm-hmmm...a classic misprint!
- Fairy Companion: Accompanies Richard on his journey.
- Fairy Godmother: Acts as one to Richard and claims to grant wishes.
- Fish out of Water: She was mis-shelved and is clueless to the horror genre.
- Magic Carpet: Has Horror rip out one of her pages and transforms it into a flying carpet.
- Magic Wand: She seems to have a bit of a faulty one but gets stronger when in the fantasy section.
- Portal Book: Able to pull fantasy-related objects from her pages like a flying carpet.
- Sassy Black Woman: Well, she is voiced by Whoopi Goldberg.
- Ship Tease: With Adventure, though she doesn't seem to want it.
- The Smurfette Principle: The only woman in Richard's group.
- Verbal Tic: "Mmm-hmmm."
- Played by: Frank Welker
- All There in the Manual: Word of God states that Horror was created with a misshapen spine, and his parents were an encyclopedia and a paperback book. As a result, Horror feels he has been mis-shelved in life and wants to gain a happy ending.
- Animate Inanimate Object: A talking book.
- Chekhov's Gunman: Horror discovers he can float after the group is separated by Moby Dick.
- Cowardly Lion / Lovable Coward: Similar to Richard, he is easily frightened despite coming from the horror section of the library, but becomes braver over time.
- Cute Monster: In the eyes of Fantasy.
- Dynamic Entry: Swings into battle like Tarzan and knocks out several pirates upon landing.
- Earn Your Happy Ending: All he wants is to be checked out and be happy.
- Falling into His Arms: A subverted version. Horror is knocked out of a bell tower and lands in Richard's arms.
- Friend to All Living Things: Horror is the most gentle of characters compared to the hot-headed Adventure and Fantasy, and wouldn't hurt a fly.
- The Grotesque: Horror is described as a "hunchbook" and is based on Quasimodo. He has a misshapen spine and torn features. Also has elements of Igor, referring to Richard as his "master".
- I Just Want to Have Friends: Too friendly and kind for the horror section, Horror just wants to have friends and a better existence.
- The Klutz: A bit clumsy and accident prone at times. He accidentally knocks Fantasy's wand out of her hand and it is eaten by the dragon, causing it to gain extra firepower and fry the flying carpet they are on.
- Sensitive Guy and Manly Man: The relationship between Horror and Adventure. Adventure is mostly mean and insulting towards Horror, and angrily chews out Horror when he comments that he could be like him (but mostly because his pride was damaged because Fantasy and Horror rescued Richard from the pirates). The two get along better after Adventure mistakes Horror for being dead.
- Technically a Smile: Gives a lopsided smile upon meeting Richard.Fantasy: Look, he's smiling.(Horror gives a weird smile)Richard: That's a smile?
Doctor Jekyll and Mr. Hyde
Dr. Jekyll / Mr. Hyde
- Played by: Leonard Nimoy
- Adaptational Villainy: While he's nice enough in the movie, the PC game's version of Dr. Jekyll has him collaborating with Hyde to rule the world.
- Ambition Is Evil: Wants to help mankind, but ends up becoming a full-on psychopath.
- Ax-Crazy: Mr. Hyde immediately starts laughing like a lunatic and attacks Richrd and his friends with a cane.
- Big Bad: While not in the film, Hyde becomes the Big Bad in the PC game.
- Body Horror: Like in the book he was from, Jekyll completely changes when he becomes Hyde. We get a brief glimpse of this when he grabs Richard and his hand begins to get hairier.
- Cane Fu: After transforming, Mr. Hyde uses Dr. Jekyll's cane to attack Richard and the others.
- Disney Villain Death: Overlaps with He's Just Hiding. We never find out Hyde's ultimate fate after falling through the hole in his floor, but he appears at the film's end, revealed to be part of the Pagemaster's Secret Test of Character.
- Evil Laugh: Mr Hyde does these a lot.
- Evil Sounds Deep: Mr Hyde' voice is more deep and guttural than Jekyll's.
- Falling Chandelier of Doom: Horror drops a chandelier on Mr. Hyde. It misses but causes Hyde to fall through a hole in the floor and dangle from a chain. Fantasy breaks the chain like a blowtorch, and we hear Mr. Hyde fall to his apparent doom. He survives and transforms back into Dr. Jekyll at the end of the film.
- Gargle Blaster: The Hyde potion, once spilt, eats through the wooden floor in a second.
- Harbinger of Impending Doom: Dr. Jekyll informs Richard that he is in grave danger for entering his house.Dr. Jekyll: My boy, I derive no pleasure in telling you, that you are in extreme danger.Richard: Danger!Dr. Jekyll: Even as we speak. In this very room waiting to strike are the forces of evil. Every man is possessed of both good and evil. But enough of that, anyone care for a drink?
- Large Ham: Mr Hyde unlike the more calm and affable Jekyll.Mr Hyde: My name is...Mr HYYYYYYYDE !!
- Mad Scientist: As in the novel, Dr. Jekyll is an ambitious scientist hoping to help mankind and rid himself of his own darkness. However, he makes a formula which instead backfires and turns him into Mr. Hyde.
- Nightmare Face: Mr. Hyde's is one to remember.
- Red Eyes, Take Warning
- Painful Transformation: The transformation is brief but pretty terrifying. Dr. Jekyll screams in agony as his body reacts to his potion, then he undergoes some body horror before becoming Mr. Hyde.
- Slasher Smile: Again, Hyde.
- Superpowered Evil Side: He just needs to drink the potion in order to become this.
- They Call Me Mr Tibbs: For Jekyll's introduction.Fantasy: Excuse me, Mr., uh...Jekyll: Doctor. Dr. Jekyll.
- Played by: George Hearn
- Ambition Is Evil: Wants to kill Moby as an act of revenge.
- Ax-Crazy: One reason why Adventure likes him.
- Dropped A Whale On Him: Tries to kill Moby Dick with a spear, only to have the whale leap out of the water and sink his ship.
- Father Neptune: Shown to be a veteran sailor and hunter.
- Gosh Dang It to Heck!: Subverted. His speech before attacking Moby is taken from the book.
- Incoming Ham: "Thar she blows!"
- Large Ham: Taken from the source material.
- Spear Carrier: Little more than a One-Scene Wonder, Captain Ahab sails into the ocean and tries to slay Moby Dick. It doesn't work.
Long John Silver
Long John Silver
- Played by: Jim Cummings
- Affably Evil: Quite polite towards Richard, wishing to employ him as a cabin boy, and departs from the island when Richard threatens him with a sword.
- Cool Sword: Has one as a pirate should.
- The Dreaded: Adventure describes him as this.
- Handicapped Badass: Needs to use a crutch in order to walk, but is very ruthless and determined.
- Jerk with a Heart of Gold: Like in the book, while he is a villain nonetheless, he is actually quite nice to Richard, reflecting how he treated Jim Hawkins in the original story. In the climax, he congratulates Richard on facing his fears.
- Large Ham: "There she be, mateys! Treasure Island!"
- The Mutiny: His crew try to pull this on him when they cannot find any treasure, only for Fantasy and Horror to arrive to rescue their friends.
- Pirate Parrot: Accompanied by a scrawny parrot.
- Talk Like a Pirate: But of course.
- "Well Done, Son!" Guy: Gives Richard his congratulations.Long John: Ah, you had pirate stuff, me lad! An' don't no one speak any different.
The DragonThe final obstacle between Richard and the exit. An enormous fire breathing dragon who attacks Richard and his friends after they wake him up.
- Big Bad: He is more or less this for the film; He was the thing that first brought Richard into the magic world. He is also the last and most dangerous obstacle that Richard and his friends have to face.
- Breath Weapon: Can breathe fire. Gets a huge power boost after eating Fantasy's wand.
- Giant Flyer: Flies on giant bat wings.
- Our Dragons Are Different: Your standard fire-breathing dragon...that also materialises in a melted rotunda artwork to chase Richard.
- Ribcage Stomach: And contains a number of children's books and molten lava!
- That's No Moon!: Mistaken for a cave until Adventure chops one of its fangs off, awakening the dragon.
- When Trees Attack: Gets paralyzed when a beanstalk grows out of its mouth.