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Literature / Half Upon a Time

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Half Upon A Time is a Fractured Fairy Tale novel by James Riley, published in 2010. It was the 2011 NCTE Notable Children's Book in the Language Arts.

The story focuses on Jack, who shares the same name as his father, the central figure of Jack and the Beanstalk. Jack is at the bottom of his class when it comes to learning Princess Rescue, a skill he sees as pointless as there are no unwed princesses left to rescue, anyway.


None, that is, until a girl named May literally falls out of the sky.

What follows is an adventure where Jack and May try to find and rescue the girl's missing grandmother, and escape the mysterious figures who seem to be hunting them. Along the way, they meet and team up with a prince named Phillip, and a few other recognizable characters as well.

The book was followed by a sequel called Twice Upon a Time, and a third book called "Once Upon The End".


Tropes from the novel:

  • Action Girl: May starts growing into this.
  • Badass Grandpa: Jack's Grandfather, though now he's more of a Retired Badass.
  • Be Careful What You Wish For:
    Jack: I should be able to just stick out my arms, and have a princess fall right into them!
  • Belligerent Sexual Tension: Jack and May, oh so much.
  • Break the Cutie: Sorry, May, but your Grandmother is the Wicked Queen.
  • Butt-Monkey: Poor Jack just can't get stop getting beat up on, can he?
  • Cannot Tell a Lie: Phillip.
  • Chekhov's Gun: The magic bridle, a magic bean that once belonged to Jack's father, and an enchanted knife taken from a witch's cabin.
  • Deadpan Snarker: Jack and May have their moments. May is particularly snarky until she trades her sarcasm to an imp in exchange for Jack's safety.
  • Downer Ending: The first novel ends with May learning that her Grandmother is actually the Wicked Queen, and that she, Jack, and Phillip have just unwittingly unleashed her on the world.
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  • Even Evil Has Loved Ones: The Wicked Queen still clearly cares for May, in her own way.
  • Even Evil Has Standards: Despite having a serious grudge against Malevolent, The Wolf King refuses to slaughter her when she's rendered helpless by Jack's bridle, and so he frees her instead.
  • Evil Weapon: What everyone assumes about the swords of The Eyes. Jack is frequently mistrusted just for carrying one.
  • Fair Folk: Several appear. One takes up residence in May's hair.
  • Fairy Godmother: Merriweather, to both Phillip and May.
  • Fairy Tale Free-for-All: Several classic fairy tale characters appear in supporting roles.
  • Fate Worse than Death: May's grandmother informs Jack that if he miscasts a spell, one of the possible consequences is that he will cease to exist.
  • Failure Hero: In one way or another, Jack keeps finding ways to fail. At first. Given that his full name is Jack the Thirteenth, this should come as no surprise.
  • Flying Broomstick: Jack and May steal one from a Witch. It seems a bit empathic, as it seems to prefer May to Jack.
  • Fractured Fairy Tale:
  • Gingerbread House: Jack and May find themselves in one after fleeing The Huntsman.
  • Guile Hero: Anytime Jack does something awesome, it owes a lot to this.
  • I'm a Humanitarian: Many of the monsters, especially the witch and the giant that Jack and May run afoul of.
  • It Was a Gift: Jack's sword, given to him while he was in the mouth of a giant.
  • Kiss of Life: Overlapping with Dude, She's Like, in a Coma!, Jack does not want to try this with an unconscious May at his grandfathers persistence. Hilarity ensues.
  • Literal Genie: How deals with the prison imp work.
  • Locking MacGyver in the Store Cupboard: Occurs twice in the candy house segment. May is able to use a knife to cut herself free of her bonds and escape the closet she's locked in, and she and Jack are able to escape the house with the witch's broom.
  • Names to Run Away from Really Fast: A few. Most notably The Black Forest and Malevolent. Actually subverted with Malevolent, as that is not her real name, but a pseudonym forced on her by her fellow fairy queens when she was exiled.
  • Nice Job Breaking It, Hero!: Nice job, Jack, May, and Phillip, for releasing the Wicked Queen back into the world with her minions.
  • Our Werewolves Are Different: The Wolf King is a Talking Animal who has learned to take human guise as he sees fit.
  • Rescue Romance: The point of Jack's school is to teach him and his fellow peasants to rescue princesses so they can marry them. Somewhat subverted, as the other students are in it more for the Kingdom they'll receive rather than the heart of the girl they're rescuing.
  • Royals Who Actually Do Something: Several in the story.
    • Phillip slays giants, looking for the one who killed his Father.
    • Malevolent is a Fairy Queen who casts powerful curses and is generally feared.
    • The Wolf King helps Jack, May, and Phillip find May's Grandmother. He also serves her in her war against the other royals who oppose her, as she is the Wicked Queen.
    • Rapunzel, Snow White, and Rose Red all led their forces against the Wicked Queen fourteen years ago. Rapunzel and Rose Red still are.
  • Scaled Up: Malevolent, who turns herself into a Dragon. It doesn't help her, because of Jack's magic bridle.
  • Skunk Stripe: May is blonde with a lock of hair dyed blue.
  • True Name: Comes up a couple of times. At one point, a witch refuses to tell Jack her name, because "names have power". And May manages to freak out a prison imp when she correctly guesses his family name.
  • Weaksauce Weakness: The Wicked Queen, who is vulnerable to Cold Iron.
  • Values Dissonance: In universe, May is perplexed that anyone would think she would be married at the age of 14. Jack, however, felt it was a reasonable question to ask.
  • Voluntary Shapeshifting: The Wolf King and Malevolent.

Example of: