- Played by: Chip Zien (OBC), Ian Bartholomew (Original London Cast), James Corden (2014 film)
An average working man whose greatest wish is to have a child. Unfortunately, the Witch cursed him to be barren due to a perceived slight by his father. In a bid to reverse this, she gives three days for him and his wife to bring her Jack's cow, Red Riding Hood's cloak, Cinderella's slipper, and some of Rapunzel's hair.
- Action Survivor: He is in no way trained to conquer the obstacles he comes across, but does so nonetheless.
- Be Careful What You Wish For: His wish for a son is granted, but when revisited in "So Happy" he and his wife complain that they have no room. In the ensuing chaos, his wife is killed.
- Changed My Mind, Kid: After he snaps out of his Heroic BSoD.
- Classical Anti-Hero: Insecure despite wanting to lift the curse himself.
- Dead Person Conversation: Two in Act II: With his father and wife.
- Everyone Calls Him "Barkeep": "The Baker."
- Five Stages of Grief: The Baker goes through these during Act II after his wife is killed.
- Happily Married: He and his wife have their ups and downs, but they obviously love each other quite a lot. Eventually subverted when she cheats on him.
- The Hero: The focal character and one of the most good-hearted among the main cast.
- Heroic BSoD: Despairing because of his wife's death, he leaves the other survivors to fight the giant. It takes a Dead Person Conversation with his father to snap him out of it.
- His Name Really Is "Barkeep": Implied. Jack and Little Red call him Mr. Baker.
- Hurting Hero: During the second half of Act II.
- Irony: He mourns his childlessness, but he keeps refusing to give away his bread to Red (who is a child) and calls her a thief for taking away and eating some of his creations.
- Loser Son of Loser Dad: The major plot of the story, as the Baker along with Jack, Red Riding Hood and Cinderella are stranded in the woods when deciding to fend of the giantess together. Becomes averted as his father tells him not to run away from his problems and faces it without him.
- Took a Level in Badass
- Stay in the Kitchen: This is the Baker's attitude in the beginning of the first act (both literally and figuratively), but he gets over it.
The Baker's Wife
The, well, Baker's Wife, a determined and practical woman who is a romantic at heart. Like him, she is motivated by the desire for a child, although she frequently asks after Cinderella's prince when she encounters the latter.
- Action Survivor: Tragically subverted when she allows herself to be seduced by Cinderella's Prince despite being a married woman, which leads to her getting killed by the giant.
- All Girls Want Bad Boys: Turned on by take charge guys.
- Anti-Hero: Type 3. She's a good person but she does a lot of morally questionable things to get what she wants, like trading beans she told Jack were magic (they turned out to be true, but she didn't know that at the time) for the cow.
- Bad "Bad Acting": When she tries to get Jack to trade/buy the magic beans for the cow. "Oh... Oh! Oh no, we mustn't give up our beans!"
- Deadpan Snarker: Moreso in the musical, but the film lets her sneak in a few lines.
- Death by Sex: She's offed shortly after her affair with Cinderella's prince.
- Dropped a Bridge on Her: She's trampled by a tree felled by the Giantess.
- Everyone Calls Her Barkeep: Though apparently her Canon Name on the film's set was Margery.
- Express Delivery: In the film, as soon as the curse is undone she immediately becomes nine months pregnant.
- Happily Married: Although she cheats on her husband in a moment of confused feelings, they seem very happily married.
- Lampshade Hanging / Leaning on the Fourth Wall: In "Moments in the Woods", the Baker's Wife sings "I'm in the wrong story". According to Word of God, Sondheim added this line after he realized that the story of the baker and his wife feels much more contemporary than the others. Joanna Gleason, who played the Baker's Wife, felt like her character was in the wrong story, and so did Sondheim. He felt like this needed acknowledgement.
- Loving a Shadow: Every time she talks to Cinderella, she sighs after the handsome Prince... but this is mostly envy for the glamorous life she associates with Princes; she later realizes her husband has many princely qualities of his own.
- Parenting the Husband: At least initially, she's sterner and more pragmatic than her husband.
- Plucky Girl: The Baker's Wife displays a take-charge attitude when searching the woods for the four items she needs and also when hunting the giant.
- Positive Discrimination: Inverted. She's the one whose more comfortable doing morally questionable things, compared to her husband.
- Your Cheating Heart: Shows minor signs of this throughout the show, longing for every prince she sees though already married. After she does commit adultery with Cinderella's prince, she spends her last song trying to justify her actions to herself.
- Played by: Ben Wright (OBC), Richard Dempsey (Original London Cast), Daniel Huttlestone (2014 film)
The feckless protagonist of Jack and the Beanstalk. Here, his story starts out much the same — he trades his beloved cow to the Baker for a handful of magic beans, and goes on to slay the giant he finds at the top of the beanstalk that grows from the beans.
- Berserk Button: Depending on the production, don't you ever DARE call him a liar.
- Cloud Cuckoo Lander: His head always seems to be in the clouds.
- Disappeared Dad: Mentioned as "not back" and never again.
- Dope Slap: Is given several by his mother in the film.
- Idiot Hero: The most idiotic.Jack's Mother: "Sometimes, I fear you're touched!"
- Introverted Cat Person: Or rather, Introverted Cow Person. He doesn't have any friends of his own because there aren't any other children in the village he lives in, and so gets all his companionship from Milky.
- Karma Houdini: He never gets any punishment for stealing from the giants and killing both of them, except the indirect death of his mother. He even gets to live with the Baker's new family.
- Lethally Stupid: To the point that his mother has reason to suspect that he was the one who destroyed the Baker's house.
- Only Friend: He claims that Milky White is this. Played for laughs.
- Playing Gertrude: He's rarely, if ever, played by an actual little boy in the play. Averted in the 2014 film where Daniel Huttlestone plays him.
- Tenor Boy
- Took a Level in Badass
- Played by: Barbara Byrne (OBC), Patsy Rowlands (Original London Cast), Tracey Ullman (2014 film)
Jack's browbeaten single mother determined to make their lives better.
- Adaptational Jerkass: She's a lot rougher towards her son in the film than in the play.
- Abusive Parent: Sorta in the film adaptation. She seemed to get angry very easily with Jack and even hits him a few times. However, she still cares for her son and wants the two of them to survive with enough money and food. She even keeps her Mama Bear moment when she tells the Giantess that she will protect her son. (See Adaptational Jerkass above)
- Anger Born of Worry: She acts rather harsh to Jack and makes it known that she thinks he's a fool, but she worries that his carelessness will get him into danger. After the giant falls into their backyard, she tracks down her son in the woods to make sure he's okay, and give him a Dope Slap.
- Be Careful What You Wish For: She wishes to better her and Jack's lives. Jack slays the Giant and steals their treasures, making him and his mother wealthy — but spurs the Giantess's anger.
- Cloud Cuckoo Landers Minder: She's the one always keeping her idiot son in line.
- Face Death with Dignity: After the Steward accidentally gives her a fatal blow to the head, she shows an almost zen calmness as she gives her last request, knowing full well that she's "on death's door" and using her last breath to plead with the Baker for Jack's safety.
- Last Request: To the Baker, to protect Jack.
- Mama Bear: She was pretty brave (and stupid) for standing up to a giant, telling her that she will protect her son at all costs.
- My Beloved Smother: She's always trying to control Jack's actions. Justified, though, as Jack can cause catastrophic damage if left alone.
- Only Sane Woman: Her son is not that bright.
- Reality Ensues: Her death—needless to say, a blow to the head hard enough to shut someone up is not going to end well...
- Violin Scam: She orders Jack to carry Milky for a very long distance out of their village and find a sucker who's gullible enough to buy the cow for 5 pounds or more since their whole village knows how sick the cow has gotten. Though this comes off as Insane Troll Logic since whoever has that much money will inspect the cow first, and as she pointed out, the cow is clearly and visibly expiring being infested with parasites and open wounds. The scam was doomed to fail since the cow died merely minutes after the Baker bought it for beans.
Little Red Riding Hood
- Played by: Danielle Ferland (OBC), Tessa Burbridge (Original London Cast), Lilla Crawford (2014 film)
The protagonist of Little Red Riding Hood, a strong-willed and fearless young girl hampered by her curiosity and naivete. Straying off the beaten path on her way to her grandmother's house leads to her discovering many things.
- Action Girl: Shows signs of this in Act II, if some of her tropes below indicate anything. After replacing her red hood with a fur coat and receiving a knife for self-defense, she becomes a Deadpan Snarking, Axe-Crazy Girl with Psycho Weapon threatening to gut any potential attackers.
- Ax-Crazy: Becomes this after she and her grandmother are cut out of the Wolf's stomach and start skinning the wolf. She threatens Jack's life just because he takes an interest in her fur cloak!
- Big Eater: Between the prologue and reaching Granny's, she eats nearly the entire basket of goods she was meant to bring a loaf of bread, a sticky bun (or four), and a few pies. She is even eating when she isn't singing her orders.
- Flat "What": To Cinderella: "You can talk to birds?"
- Girl with Psycho Weapon: She's supposed to be young and cute...until she pulls a knife on you.
- Girlish Pigtails: Lilla Crawford's portrayal of her has these throughout the whole film.
- Heroic Comedic Sociopath: Seemingly has very little regard for everybody else at first. This is played for humor. Part of her storyline is learning morality.
- I Have a Family: She brings up her grandmother as an excuse to take away the baked goodies from the married couple (the Baker keeps objecting, his wife enables her) but then Red keeps eating them herself to which the baker comments she might not save any for grandma.
- Knife Nut: Given to her by her grandmother for protection. She's not afraid to brandish it on a stranger for the smallest slight.
- Large Ham: Depending on the production, her screaming can be either heartbreaking or hilarious.
- Little Miss Badass: She's a young girl.
- Little Red Fighting Hood: She does get eaten by the wolf, and needs to be rescued. After that, though? For starters, she made her new cloak herself — from the wolf's pelt. After this, she is a Sociopathic Hero. The work goes in a different direction than the norm though as part of the Character Development involves her learning morality.
- Pretty in Mink: She swaps her traditional red cape for a fur one made from the skins of the wolf.
- Took a Level in Badass: After being eaten by the wolf, her granny gives her a knife that she uses with abandon at the slightest provocation.
- Unwitting Instigator of Doom: Had she not goaded Jack to return to the Giant's castle and steal the harp, the Giantess would not have been so angry. Of course, all the main characters are to blame.
- Played by: Robert Westernberg (OBC), Clive Carter (Original London Cast), Johnny Depp (2014 film)
- Advertised Extra: Plastered alongside all of the other main characters in promotional material, only to be killed off within the first 29 minutes.
- The Big Bad Wolf: Unsurprisingly.
- Coat Full of Contraband: In the movie version, the Wolf opens his coat to show a display of candy when he is trying to lure Little Red Riding Hood off the path.
- Disc-One Final Boss: The Baker and Little Red have no problem taking care of him. And then Act II happens.
- Covers Always Lie: The covers depicted Johnny Depp to play as one of the princes or at least a major character in the film, complete with the corresponding black leather jacket with studs, but is instead played only as the role of the Big Bad Wolf who only took five minutes of spotlight before being killed off by the Baker right after he was successful in eating Red Riding Hood.
- Fan Disservice: He has a visible penis in some versions.
- Minor Character, Major Song: He sings most of "Hello, Little Girl", a song about how he hungers for Little Red Riding Hood.
- Menacing Stroll
- Villain Love Song: His song, naturally.
Neighbor to the Baker and his wife and foster mother to Rapunzel. She's the one who cursed them to be barren, but cannot undo the curse until they complete her Fetch Quest. While vain, self-serving, and sarcastic, as the show goes on the viewers see that she's insecure, lonely, and ultimately just as human as everybody else.
- Abusive Parents: Locks her adopted daughter in a tower all her life, and then gets snippy when the girl wants to leave. Based on some of her lyrics in "The Witch's Lament", she may gone too far to preserve Rapunzel's characteristics.
- Above Good and Evil"I'm not good, I'm not nice, I'm just right."
- Adaptational Badass: Well the character she's based on, the Witch from Rapunzel didn't seem to have any magic at all. Certainly not the power to teleport anywhere or resurrect dead cows.
- Adaptational Villainy: She's surprisingly more evil in the film adaptation. Since she doesn't witness Rapunzel die and thus go into a BSoD Song, she's left without motivation to want Jack handed over to the Giantess. Instead, the first thing she says to the Giantess in the movie is basically, "We'll get the boy for you, don't worry'.
- Anti-Villain: She cursed the Baker's family, she was overprotective of her daughter, she wanted to sacrifice Jack to make the Giantess go away, AND she started throwing beans during The Last Midnight to summon more giants, but she was NOT the villain of the play.
- Brought Down to Normal: She loses her powers at the end of Act I.
- Broken Bird: Her misanthropy and belief that "the world is dark and wild" must come from somewhere, although we never learn exactly what happened. We do get a hint when she sings Lament:Couldn't you stay content / safe behind walls / as I / could not?
- Casting Gag: A 2012 production features Donna Murphy, who previously voiced Rapunzel's stepmother in Disney's Tangled, as the witch.
- Death Glare: The filmed version (and several stage versions) have her deliver a glorious (and often hilarious) one to the Baker when he says, "Giants never strike the same place twice."
- Dark Action Girl: Does several evil deeds, and is probably the biggest badass in the show.
- Dragged Off to Hell: One interpretation of the end of "Last Midnight."
- Driven to Suicide: Another. Of course, whether or not she actually died is debatable.
- Dynamic Entry: She makes her entrance in the movie by smashing the bakery door.
- Evil Matriarch
- For the Evulz: Because watching the Baker's father cry and the Baker's mother die when she claimed Rapunzel wasn't enough to mollify the Witch, she cursed the Baker to never have children.
- Have a Gay Old Time: One of the lyrics in her rap about the Baker's father stealing her vegetables: "He was robbing me, raping me". The original definition of the word was "destruction or spoiling of an area" - which is clearly the definition the Witch is using here.
- Hot Witch: Used to be agelessly beautiful and is looking to break the curse to reclaim it. She does but loses her powers, effectively negating the 'witch' part of the trope.
- Hypocrite: She participates in the song "Your Fault", but then when the ultimate blame falls on her, she accuses them of only caring about the blame ("Last Midnight").
- Hypocritical Humor: After the Giantess destroys the Baker's home...Baker: Did you do this to our home!?
Witch: Always thinking of yourselves. (beat) LOOK AT MY GARDEN!
- I Was Quite a Looker: She appears as an ugly old hag, but when she drinks the potion she's reverted to her beautiful past self.
- Jerkass Has a Point: While she isn't the nicest person out there she does have a point that if they don't give Jack to the Giant she'll level half the kingdom. It's not a nice thing to do but the only option they have in that moment.
- Jerk with a Heart of Gold: The Witch is more than just a classic villain, especially considering her moment of anguish after Rapunzel dies, and the fact that she, of all people, is the one who sings the beautiful "Children Will Listen" at the end.
- Knight Templar Parent
- Large Ham
- My Beloved Smother
- Only Sane Woman: The Witch has elements of this in Act Two, when she shows herself to be the only person who understands the gravity of the situation, and the unpleasant things that may need to be done to solve it.
- Parents as People: It's safe to say that keeping a girl locked in a tower for her whole life is not what one would call "good parenting," but it's also clear that the Witch really does love her, and a lot of her dialogue and lyrics indicate that she genuinely believed she was doing the right thing.
- Punished with Ugly: As punishment for losing the magic beans in her garden, she was turned into an old hag.
- Rhymes on a Dime
- Screw This, I'm Outta Here!: In a truly epic fashion at the end of "Last Midnight," The witch throws away every last bean to bring a horrible curse on herself just to get away from everyone else.
- Strawman Has a Point: Deconstructed Trope and In-Universe Example during The Last Midnight. She brings up the valid point about Jack being responsible for the Giant's Wife rampaging throughout the kingdom, and that the best solution at the moment is to bring him to her. The others are against this, knowing that she'll kill him even though more people will die if the Giant doesn't get Jack fast. The fact that they are against her simply because she's the Witch, and therefore, not to be trusted drives her up the wall. She turns it against them, saying that by refusing to give Jack to the Giant at the expense doesn't make them good, "just nice" and that while she may not be good or nice, she's just right. It delves into "The Reason You Suck" Speech, calling them no better than her and that the Baker's son will end up becoming just like them, a liar and thief, but at this point, she is so frustrated she just says "Why bother?! You'll just do what you do..." and throws away the last of her beans in an effort to get away from them. When she vanishes, everyone realizes that she was right and that their actions were not great in hindsight. This becomes reconstructed, with the Baker and Cinderella admitting that "Witches can be right", but that didn't mean that her option was the only solution in the end, with the others deciding the rampage would end if they killed the Giant first.
- Token Evil Teammate
- Vain Sorceress: Deconstructed with the Witch. She trades her powers in to get back her (rightfully) good looks, only to massively regret it later. She's not so much Ax-Crazy over being ugly as she is weary of being treated like a freak.
- Villainous Breakdown: After Rapunzel's death, quickly leading to "Last Midnight" and her subsequent abandonment of the rest of the cast.
- What the Hell, Hero?: "Last Midnight" is one big one to all the main characters.
- Wicked Witch: Played with. Although having the stereotypical look of a Wicked Witch, not to mention doing a couple of rather nasty things, she's still helping the protagonists to an extent.
- Played by: Kim Crosby (OBC), Jaqueline Dankworth (Original London Cast), Anna Kendrick (2014 film)
Kind, gentle, earnest, and downtrodden by her stepmother and stepsisters, Cinderella's greatest wish is to attend the royal family's festival. There, one of the princes falls in love with her, but she fears that he will not love her should he realize she is a peasant.
- Action Girl: She becomes this in Act 2. She Took a Level in Badass, with Cinderella venturing into the woods on her own and dumping her "Prince Charming" (who actually turned out to be a douche), and is one of the only four survivors at the end of the musical, and helps defeat the Big Bad.
- Action Survivor: She is not particularly adept at fighting off all the craziness that comes her way in the musical. Nonetheless, she proves to be extremely resourceful, determined, and surprisingly courageous. And along with three other characters, she successfully manages to overcome and defeat the Big Bad in the end, after everyone else dies.
- Be Careful What You Wish For: Her recurring theme of "I wish" kick-starts both acts.
- Being Good Sucks: Cinderella points out in her singing that the only reward she gets from her kindness is continuing abuse and slaps in the face.
- Book-Ends: She starts and ends the musical with "I wish."
- Butt-Monkey: She's the toilet paper of her family. Very near literally, since she's always covered in dust, dirt and possibly food stains from her cooking and cleaning duties.
- Cinderella Circumstances: Naturally, she's put upon by her stepmother and stepsisters.
- Cool Big Sis: She serves as a guiding feminine influence to Little Red.
- Cute Clumsy Girl: While wearing the gold slippers—they're terrible to walk in. Lampshaded by the Baker's Wife:Baker's Wife: My, you do take an awful lot of spills, don't you?
- The Ditherer: Highlighted in "On the Steps of the Palace," when she can't decide whether to let the Prince catch her or to run away back home. She decides not to decide by leaving a shoe on the stair smeared with pitch.
- Extreme Doormat: Starts off as this, but later Grows A Spine when she stands up to her Prince and dumps him for his philandering ways.
- Friend to All Living Things: Her sidekick birds.
- Grew a Spine: See the Extreme Doormat entry.
- Loving a Shadow: She admits that she will always love "the prince at the ball."
- Meganekko: In the original cast, but not universally. And only for the first song.
- Missing Mom: However, she can still talk to her mom's spirit at her grave. Until the Giantess crushes the grave, anyway.
- Nice Girl: She's kind, friendly, and tries her best to remain hopeful and goodhearted in spite of her stepfamily's abuse. Part of her character development is learning that this doesn't mean she has to be a walkover.
- Pimped-Out Dress: But of course. It's created by magic.
- The Pratfall: Cinderella has a tough time running in those shoes...
- Princess Classic: Subverted in that she is better developed in the musical, with more of her own flaws.
- Royals Who Actually Do Something: Played With in that Cinderella tries to help, but has to dress as a commoner to do so.
- Slapstick Knows No Gender: See The Pratfall, above.
- The Soprano: While she's not the typical Ingenue, she still trills and hits the high notes.
- Speaks Fluent Animal: Can communicate well with birds. The absurdity of this is lampshaded by Little Red.
- Swiss Army Tears: Cinderella's tears that she wept for her late mother is what helped grow the tree that allowed her to meet her mother's ghost or reincarnation as an angel.
- Take a Third Option: Her choice is to flee from the prince a third time or stay and be caught. Her decision is "not to decide" and run away, but leave her shoe behind as a way for him to find her.
- Team Mom
- Took a Level in Badass
- Unwitting Instigator of Doom: Had she not thrown away the bean that the Baker's Wife traded her for her slipper, the Giantess would have had no way to climb down and wreak havoc. Of course, all the main characters are to blame in one way or another.
- Played by: Pamela Winslow (OBC), Mary Lincoln (Original London Cast), MacKenzie Mauzy (2014 film)
Protagonist of Rapunzel. The Witch's ward, a beautiful but unstable maiden whom the Witch locked in a tower for her entire life.
- Ambiguous Disorder: Possibly postpartum depression.
- Beautiful Singing Voice: Her lovely yet haunting voice carries through the woods and is the only thing that can calm the Witch in the midst of her tantrums, and charms the Prince, before he basks in her beauty.
- Break the Cutie: While not the Witch's intent, her treatment of Rapunzel eventually caused her to be subject to hysterics.
- The Ditz
- Driven to Suicide: One interpretation of her running into the path of the Giant's foot.
- Dropped a Bridge on Her: Or perhaps more accurately, a foot.
- Dumb Blonde: Rapunzel shows elements of this in act one.
- Girl in the Tower: Of course. Deconstructed as well, as all that isolation contributed greatly to her instability.
- Hair of Gold, Heart of Gold: Played straight in Act I; her mental instability subverts it by Act II.
- Hysterical Woman: By the time of her death she's certainly this.
- Long-Lost Relative: She's the Baker's younger sister, who was taken at birth from their parents because their father stole greens from the Witch's garden for their mother. Only the Witch acknowledges this in-story, however.
- Mood-Swinger: It's mentioned by her prince in Act II that she swings moods pretty quickly.
- The Ophelia: She's lovely, but unstable thanks to her time in the tower and the Witch's treatment of her.
- Rapunzel Hair: Of course. Her extremely long hair is actually part of the Witch's Fetch Quest. She loses it later.
- "The Reason You Suck" Speech: Finally tells off the Witch for sticking her in a tower all her life, abandoning her, blinding her Prince, and generally being a jerkass.Witch: (defensive, yet sincere) I was just trying to be a good mother.
- Rich in Dollars, Poor in Sense: Even after becoming a princess, she still doesn't have the best grip on life. She was kept in a tower her whole life.
- Screaming Woman: She lets out a loud scream at the end of the "Agony" reprise.
- The Soprano: Averted by her character, but vocally? You'd better believe it.
- Spared by the Adaptation: In the 2014 film. She is not Driven to Suicide and she gets to live happily ever after with her prince.
- Swiss Army Tears: Her tears heal her prince's blindness, as in the original.
- The Unintelligible: Rapunzel only has a few scenes where she actually talks. The rest of the show, she expresses her feelings by "humming a lighthearted air" and screaming. Somewhat lampshaded by her prince. After the reprise of "Agony," Rapunzel, out of nowhere, lets out an enormous scream. The prince doesn't look the slightest bit shocked and says "Rapunzel," in deadpan.
- Played by: Tom Alredge (OBC), Nicholas Parsons (Original London Cast). Role omitted from the film version.
The cheery, intelligent narrator of the story.
- Adapted Out: In the 2014 film, the Baker takes over the Narrator role.
- Anyone Can Die: Even the narrator.
- "You're going to be on the INSIDE, now!"
- "Could Have Avoided This!" Plot: When the characters try to offer the Narrator to the Giantess as a sacrifice, the Narrator reminds them that the story would be lost if he was obliterated. Regardless of this, however, the Witch gives the Narrator to the Giantess anyway, and as soon as the Giantess sees that the Narrator isn't Jack, the Narrator is dropped from the Giantess's hand and killed. Possibly concerned with the subsequent events of the story without the Narrator, the Baker's Wife points out: "We might have thought of something else."
- First-Person Smartass
- Interactive Narrator
- Infant Immortality: In the productions where The Narrator is a child this is completely averted and he's still killed by the Giantess in the story.
- Lemony Narrator: Ends up biting him in the ass. See below.
- Only Sane Man
- Rage Against the Author: The rest of the characters essentially feed him to the giant, although it's the Witch that does it right after the other characters realize how lost they would be without him. See above for details.
- The Runaway: Several new productions turn the narrator into a young boy instead of a grown man with the addition of a new Book-Ends story where he runs away to live in the woods after a fight with his father. Said father is revealed to be played by the same actor as The Baker and is the one who told the boy the story in the first place.
- Played by: Robert Westenberg (OBC), Clive Carter (Original London Cast), Chris Pine (2014 film)
Cinderella's prince, who falls in love with her after dancing with her at the ball.
- Afraid of BloodBut even one prick - it's my thing about blood!
- The Casanova: Associated by his character quote.
- Distracted by the Sexy: Off to bring down the Giant...and who's this lovely thing?
- Fake Ultimate Hero: Says a lot but does nothing against the giant.
- Large Ham: Oh very VERY much so. Especially in "Agony" and the reprise.
- Prince Charmless: After he engaged himself with the Baker's Wife, he immediately told her that it was just a moment in the woods, meaning it's something that was never to happen again. His womanizing ways result in the Baker's Wife staying in the area where she dies and Cinderella leaving him because of his brief affair. And then, he learns nothing and goes on to pursue a relationship with Sleeping Beauty.
- Royals Who Actually Try To Do Something: He never actually finds the Giant, but besides Cinderella herself, he's the only member of the royal family to actually get off his ass and go looking for her.
- Wanting Is Better Than Having: Moreso than anyone else in the story; after finally finding his runaway maiden in Cinderella, he grows bored with her and more intrigued with the mysterious Sleeping Beauty. If you pay attention, the "I Want" Song he shares with his brother are not about the actual women they're trying to woo, but entirely about the feeling of wanting something but not being able to get it."The harder to get, the better to have."
- Your Cheating Heart: Even after getting married to Cinderella, he still has a dalliance with the Baker's Wife and ends up with Sleeping Beauty.
- Played by: Chuck Wagner (OBC), Mark Tinkler (Original London Cast), Billy Magnussen (2014 film)
Cinderella's prince's younger brother, who falls in love with Rapunzel.
- Adaptational Heroism: He remains faithful to Rapunzel in the 2014 film.
- Adorkable: In the 2014 film.
- The Casanova: Depending on the production, he's a (slightly) more sympathetic version of this than his elder brother. The trope is averted entirely in the 2014 film.
- Eye Scream: He's blinded by falling into thorns after the witch pushes him from the tower. He gets better.
- Large Ham: Engaging in Ham-to-Ham Combat with his brother.
- Prince Charmless: In the play. He's nicer in the 2014 film.
- Wanting Is Better Than Having: Along with his brother, this is his main character flaw. After rescuing Rapunzel from her tower he quickly grows bored and strays toward Snow White. In the 2014 film he manages to stay with his (still living) wife though, letting him grow out of this.
- Why Did It Have To Be Dwarves?: He's evidently terrified of dwarfs. Unfortunately for him, they're the only thing standing between him and his next fling, Snow White.
- Played by: Merle Louise (OBC, voice), Eunice Gayson (Original London Cast, voice), Frances de la Tour (2014 film)
- Attack of the 50-Foot Whatever: Attack of the 50-foot giant woman, to be precise. As she squashes her way in destroying the Woods, ruining the previous lives of the main characters in her wake. Although, she is not exactly the 50-foot woman you are expecting.
- Anti-Villain: Most of the deaths she causes are accidents and if she were human, Jack would have been thrown into a dungeon for the things he did to her and her husband.
- Blind Without 'Em: She loses her glasses and can't look for Jack by sight.
- Genius Bruiser: "NOT ALL GIANTS ARE DUMB!"
- Mrs. Robinson: Implied in "Giants in the Sky", where Jack describes how she gave him food and rest during his stay.
- No Indoor Voice: A given for a giant. The volume for her dialogue is always amplified to suggest her enormous appearance, and she yells even louder the angrier she gets.
- The Unseen: She's usually portrayed as an unseen character voiced by an offstage actress, with the characters onstage "looking up at her" to signify her presence. Some productions work their way around this; in the Broadway revival and Hollywood Bowl staging, we see her enormous shadow towering over the cast, while in the outdoor productions, she's portrayed as a giant, puppeteered face. The film subverts this by showing her face during the climax, though her face is obscured in her first appearance as a Mythology Gag.
- Well-Intentioned Extremist: She explained her reasons when she was introduced. She had every right to be upset with Jack.
- Vengeful Widow: Is (reasonably) furious with Jack for mugging then murdering her husband.
- Played by: Edmund Lyndeck (OBC), John Rogan (Original London Cast). Role omitted from the film.
- Played by: Philip Hoffman (OBC), Peter Ledbury (Original London Cast), Richard Glover (2014 film)
- Adaptational Heroism: In the 2014 film. Hero is a huge stretch, but he seemed genuinely regretful for what he did to Jack's mother.
- Dirty Coward: If refusing to give up his life for others and justifying his killing of Jack's mother is of any indication.
- Hypocrite: He defends his killing of Jack's mother as being necessary for the greater good, but when the Witch suggests that it's in his line of duty to sacrifice his life, he immediately declares that he's not dying for anyone.
- Karma Houdini: He literally gets away with murder.
- Obstructive Bureaucrat: He doesn't make policy, he just follows it.
The Mysterious Man
- Played by: Tom Alredge (OBC), John Rogan (Original London Cast), Simon Russell Beale (2014 film)
- Adapted Out: He's given very little screen time in the film adaptation. He only shows up when the Baker is trying to run away and he briefly encourages him to turn around and help stop the Giantess. It's also implied that he's already dead and didn't die trying to help his son and daughter-in-law get their wish granted.
- Catchphrase Interruptus: His enigmatic introduction, the final time he offers it; overlaps with Rule of Three.
- Dead Person Conversation: When the Baker attempts to run away in Act 2, the Man appears and talks him out of it.
- Like Father, Like Son: Towards the end of "No More", he and the Baker both say this. This naturally convinces the Baker not to run away and help stop the Giantess.
- Luke, I Am Your Father: He's the Baker and Rapunzel's father, although only the Baker ever finds this out. He doesn't actually say it, though, preferring to remain unknown; it's the Witch who spills the beans.
- No Name Given
- Older and Wiser: During "No More", he points out how stupid it is to run away from your problems and that it makes it harder to live with yourself. Obviously, this was his biggest regret, leaving his son and afraid to face his mistakes head-on.