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Half Upon a Time

Book #1 of Half Upon a Time



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About The Book

In this hilarious fractured fairy tale series from New York Times bestselling author James Riley, Jack, and “punk princess” May must navigate twists and turns unlike anything you’ve seen before!

Jack lives in a fantasy world. Really. He's the son of the infamous Jack who stole the magic beans from the giant, and he's working hard to restore his family's reputation. He finds the perfect opportunity when a “princess” lands in front of him, apparently from the land of Punk, as her Punk Princess sweatshirt implies. May is from our world, and she’s utterly confused to find herself in the midst of the fairy tale characters she has read about. But Jack and May have more in common than they realize—and together, they embark on a hilarious and wild adventre in this highly accessible, modern middle grade fantasy novel.


Half Upon a Time Chapter 1
Once upon a time, Jack wouldn’t have been caught dead in a princess rescue. Yet here he was, in the middle of a cave—a dark and stupid cave—on his way to do just that. This was all such a waste of time, and after that last fight with what was apparently supposed to be a troll, his arm really hurt.

From deep within the cave came what was probably supposed to be a bloodcurdling roar. Jack sighed, rolled his eyes, and slowed down to wait. A roar like that could only mean bad things . . . and sure enough, a ball of fire came burning down the corridor, exploding just a few inches from his left arm. The heat caused him to jerk his body to the right, saving him from the second fireball, which blew through the spot he’d just been standing in.

“Hey!” Jack yelled indignantly. “You almost hit me!” Without waiting for a reply, he dropped to his knees, yanked out the blunt prop sword he’d been given, and whipped it end over end toward the source of the fireballs.

A second later Jack heard a dull thunk, followed by a groan and what sounded like a body hitting the cave floor. He smiled, then helped himself to his feet and continued on, the corridor now thankfully free of fireballs. As he walked, he looked himself over, realizing with annoyance that somewhere along the line his tan shirt and pants had both been ripped. Perfect. As if he had that many clothes to begin with.

A bit deeper in, a bright green dragon mask lay on the floor in two separate pieces, split by the otherwise completely useless sword. Just past the mask was an unconscious boy dressed all in green, a deep red bruise spreading over his face. Apparently, Jack’s aim had been better than he thought.

He briefly felt bad about knocking the boy out, but then remembered how close the fireballs had come, and all guilt disappeared. Picking up his prop sword, Jack started to leave when a thought stopped him in his tracks: Why play by the rules?

There it was, on the boy’s right hand: a sparkling red ring. Jack quickly worked the ring off the boy’s finger, then slid it onto his own. Satisfied, he started back down the hall, trying to ignore the growing ache in his shoulder. Stupid fake troll. At least the fake dragon had missed.

A bit farther in, torches flickered on the cave walls, creating what would have been an eerie effect if it hadn’t been so transparently designed to be. Again, Jack slowed down, moving as silently as he could despite the sword banging against his leg at every step. As the torchlight grew brighter and the cave started to widen, Jack stopped completely.

This was it . . . the final challenge. The first challenge required a strong arm, he’d been told, though if the pain in his shoulder was any indication, his arm hadn’t exactly been up to it. The second challenge took a brave heart, facing the fireballs. And the final challenge, the most difficult of all, could only be won by a wise head.

Wise, huh? This might not end well.

Still, it couldn’t hurt to get a little information before rushing in. Jack drew his sword and angled it around the corner. In the sword’s reflection, he saw two torches hanging from the ceiling over an old, blackened stone altar. Strapped to the altar was what looked to be a teenage boy in a white dress, a golden tiara decorating his blond hair.

A boy playing the princess? Classy.

Over the boy in the dress stood a man wearing all brown, holding a knife to the boy’s chest. On the other side of the room, a hunched old woman leaned against a large staff. The woman’s black robe covered everything but her wart-infested nose, which looked more like a carrot than anything.

“My knight will rescue me,” Jack heard the boy princess on the altar say in an unnaturally high-pitched voice. “He will! Just you wait!”

Jack sighed. A knight? Yikes. He fiddled with the ring a bit to ready it, then prepared himself to move quickly, knowing he was going to need the element of surprise if he had any hope of saving the boy . . . princess . . . whatever.

“The knight is here,” the woman in black hissed.

Okay, apparently surprise was out. Still, even if they knew he was there, maybe Jack could still throw them a bit.

“I am here,” Jack said, stepping out from around the corner. “But . . . I surrender.” With that, he held his sword up, then slowly placed it on the ground.

“You what?!” the wart-covered woman said.

“You what?!” the boy princess said.

“I surrender,” Jack repeated, stepping away from the sword. “You win.”

The man in brown held the knife closer to the fake princess. “It’s some kind of trick,” he said.

The woman nodded. “I agree. Cut out the princess’s heart!”

“No!” the boy princess screamed, his voice breaking in panic.

“Quiet, princess!” the man in brown said, lifting his knife high into the air. “The witch orders, and I obey!”

“And as for you, little hero,” the witch said, “you will join your princess in death!” With that, she aimed a gnarled wand in Jack’s direction, shouted a magic word, and shot a bolt of lightning straight at him.

Jack dropped, then quickly dodged a second blast by rolling to the right.

“Princess, your heart is mine!” the man in brown screamed, driving the knife down toward the boy on the altar.

“I have you now!” the old woman shouted, aiming her wand right at Jack.

Jack glanced quickly between the woman and the man in brown. He could either save himself or the princess, there was no time to do both. He instantly made his decision, aimed the ring, and fired it . . .

Right at the witch.

A fireball three times the size of the previous ones erupted from the ring and exploded into the witch’s chest, lighting her black robe on fire. The witch screamed in terror as she frantically tore at her flaming clothing. The man in brown gasped, then rushed to the witch’s side, dropping his knife to the ground as he ran.

Jack used the distraction to retrieve his sword, then duck under the altar to quickly cut through the captive boy’s bonds. “Get up, Princess!” he hissed, standing back up. “We have to—”

And then he stopped, realizing he was too late. The boy princess’s white gown was now stained with some kind of red liquid, and he lay on the altar with his tongue sticking out, not moving.

Dropping his sword to the ground, Jack put his head in his hands. He had failed. The princess was dead.

The furious witch grabbed Jack by his shirt and pushed him against the wall, her eyes narrowed dangerously and her fake nose singed. “Jack!” she roared. “You could have killed me!”

“I know, I’m sorry!” he said, his face turning red. “I didn’t know it would do that! When Stephen used the ring, the fireballs were a lot smaller. . . .” He quickly removed the magic ring and held it out to the woman. She glared at him for a second before grabbing it from his hand. Then she smacked him in the head.

“I don’t care what Stephen did,” Julia, his teacher, told him as she tore off the rest of her makeup. “He knew enough to miss you! You, on the other hand, aimed right at me!”

“Okay, ow, first of all!” Jack said, rubbing his head. “Second of all, you said to treat this test like it was real. And you were shooting lightning at me! What was I supposed to do?!”

“Um,” said the princess from the altar, “can someone rescue me already?” The princess’s voice had gotten remarkably deeper since she “died.” Jack took a closer look and recognized Bertrand, one of the other boys from the village. Apparently Jack had missed some of the ropes, and Bertrand’s arms were still tied down.

Jack rolled his eyes. “Rescue yourself,” he said, tossing his fake sword to the “princess.” It hit the boy in his stomach, knocking the wind out of him.

“Well, congratulations, Jack,” Julia said as she finished removing her costume. “You failed. Not only did you handle every single situation wrong—every single one!—but you went after me when the real threat was the witch’s servant. He killed the princess, Jack!”

“But you were attacking me!” Jack protested. “If I had saved her, I would have died. And then what good would I have been to either of us?”

“And what good were you now?” Julia asked as the man in brown, Jack’s teacher Stewart, quietly walked over to untie the still complaining princess.

“It’s all useless anyway,” Jack said, his face burning from his failure. “We all know there are no unmarried princesses left. Even if there were, I don’t want to marry anyone, let alone some stuck-up royal. I’m just fine where I am!”

Jack turned to leave, but Julia grabbed his arm. “This is important, Jack. You’re the son of a . . . well, a . . .”

“A criminal?” Jack said, his eyes narrowing.

“And I don’t want you to follow his lead,” Julia said. “This is for your own good! Being a hero, rescuing a princess, killing a dragon . . . these could really turn your life around! At least, if you survive long enough.” She glared at him. “You’re the only one in your entire class to fail the princess rescue test. Just go home, Jack. We’ll talk about this later.”

Jack sighed, and turned to leave. “I don’t care how the world works,” he said over his shoulder. “All this? It isn’t me.”

“And it never will be at this rate,” Julia said, helping Stewart to yank the ropes off the fake princess.

“Thanks for nothing, Jack!” the “princess” yelled at him, his wig and tiara falling off as he sat up.

The walk back through the cave was a bit more peaceful this time, though that wouldn’t last long. His grandfather would be waiting, and Jack’s test results weren’t going to go over too well.

Outside, the brightly setting sun blinded him for a moment. He raised a hand up to block it, as the green trees of summer weren’t helping too much in that regard. He realized that it wouldn’t be much longer before the trees picked themselves up and migrated to the warmer south, leaving their dead, leafless brothers behind.

Lucky trees.

Between those trees, an old man tapped his foot impatiently. Jack’s grandfather was covered in three or four layers of different-colored clothing, while his long white beard poked out from his shirt in several places. None of that was out of the ordinary, though. The tiny, golden girl sitting on his grandfather’s shoulder, however, was a bit unusual. The girl’s wings shimmered in the sunlight as she flapped them absently.

“Hi, Grandpa,” Jack said, hoping a smile would help hide his failure. “New friend?”

His grandfather snorted, then gently offered his palm to the fairy on his shoulder. The creature daintily stepped into it, smiling shyly up at Jack as his grandfather walked over. “Just caught that bully Robert hunting some of these things,” the old man said. “The other three flew off when I rescued them, but this one seems to have a thing for me.”

Before he could even finish speaking, though, the fairy jumped out of his hand and flew over to Jack. She landed on his head, settled herself into his hair, and let out a contented sigh.

“Or not,” his grandfather said with a grunt. “How did the test go?”

Jack took in a deep breath, then blew it out without a word.

“Right,” said his grandfather, nodding. “Can’t say I’m surprised. What was the problem this time?”

Jack turned red. “I kinda let the princess die.”

His grandfather groaned. “You do realize that’s not a good thing, right?” the old man asked.

“So I’m told,” Jack said.

His grandfather patted him on the shoulder. “You’ll save her next time. Until then, you’ll practice every minute that you’re not working in the fields.”

And there it was, pretty much the worst punishment his grandfather could have laid down. The last thing Jack wanted to do was practice more princess rescuing. The whole thing was just so useless!

“It’s not useless,” his grandfather said, apparently reading his mind. “You think I’m going to let my only grandson stay a farmer for the rest of his life? That’s a job for kids too young or adults too old to go out on a proper adventure. Now, let’s get back to the cottage. There’s a chill in the air.”

“You realize it’s the middle of summer, right?” Jack asked as they started home. “I’m pretty sure any chill is just in your head.”

That earned Jack a whack on the head from his grandfather’s cane. “I fought an ice giant, you little idiot!” the old man snapped. “The monster froze my bones to their very core, and they’ve never properly healed! Usually it’s worse when I’m around the truly stupid.” He gave Jack a dark look. “You see where I’m going with this.”

“I’ll start a fire when we get home,” Jack said with a sigh. On top of his head, the fairy made herself a little nest, tugging some of his hair in the process. Unlike this one, most fairies were shy, scared of humans for a good reason: Their wings sold pretty well to wizards and witches for their magic. The practice was horribly cruel, but that didn’t stop some of the village boys from hunting the little fairies.

“A fire’s a start,” the old man said. “And then tomorrow we’ll go over my adventuring lessons again.”

Jack gritted his teeth. “Grandpa, I’m not going to waste my time anymore!” he shouted. “I’m not you . . . and I’m definitely not my father. What’s the point, anyway? There aren’t any unmarried princesses left!”

“And how would you know?!” his grandfather shouted back. “You’re not even looking! If you go looking for adventure, it will find you! At least, it would if you had the brains nature gave your little fairy friend—the one who’s scratching her head with her foot, I might add.”

“If adventure’s going to find me,” Jack growled angrily, “it can find me right here. If you’re right, it shouldn’t matter where I am. I should be able to just stick out my arms and have a princess fall right into them!”

He stuck out his arms to highlight how stupid his grandfather’s argument was.

Above him, a circle of blue fire exploded open in the middle of the air. Out of the middle of the flaming circle, a person fell to the ground less than a foot from Jack’s outstretched arms.

For a second, both Jack and his grandfather were too shocked to say anything.

As usual, though, his grandfather recovered first.

“You really have to work on your aim, boy,” the old man said.

Jack quickly ran forward to see if the person—a girl—was hurt. She was lying on her stomach, so Jack quickly turned her over, sighing in relief when he saw she was still breathing. He looked her over, trying to figure out if she’d broken anything, but she seemed okay . . . that was, other than her odd appearance.

The strangest thing had to be the streak of startling blue playing through the girl’s dirty blond hair. That couldn’t have been natural; some sort of magic had to have been involved. Not that her clothing was normal, either. Her pants were dark blue, worn through in some places but almost new in others. Her black shirt was a much thinner material than her pants and barely had any sleeves. And then Jack saw something that made him gasp in surprise.

“What?” his grandfather asked, creeping up behind Jack to look. “Is it dead?”

The old man noticed what Jack had seen, and he leapt into the air, almost giddy with excitement. “Jack, my boy!” he shouted. “You’ve done it, you’ve found one!”

Jack shook his head, still staring at the girl. She couldn’t be . . . could she? He read the words on her shirt again, out loud this time. “Punk . . . Princess.”

This girl was a princess? And where exactly was Punk?

Reading Group Guide

A Reading Group Guide to

Half Upon a Time

By James Riley


Discussion Questions

1. Half Upon a Time is full of references to fairy tales and classic stories. How many traditional characters and elements can you identify and name? In what ways do they add humor to the story? In what ways do they influence your expectations of the plot, conflict, and characters?

2. How does the symbolism in the story affect what you’re reading it? For example, if the Wolf King were the Sheep King, how would you expect his character and motives to be different? If the Black Forest were the Orange Forest, would it still be as threatening?

3. At one point when things aren’t going well, May tells Jack, “This isn’t how fairy tales work.” How do fairy tales work? Is it fair to always expect there to be a “happily ever after?” How do you feel when you read or watch a story without a happy ending? Can you name a satisfying story that has an unhappy ending?

4. From the beginning of Chapter 30, “The ride to Malevolent’s castle combined at least three of Jack’s top ten least favorite things.” Name your top ten least favorite things, and ask a few friends for their lists. Do you have any common dislikes? Why is it important for a story to show both a character’s strengths and weaknesses?

5. May tells Jack that “Heroes always know they’re right and always know what to do. They never have any doubts.” Do you believe this? Can you give examples from this book or others to prove, or disprove, this idea? Do you think Jack is a hero? Is Phillip? 

6. Jack tells Eudora that he has “some magical stuff” but that he can’t actually do magic. What’s the difference? Do you think it’s better to know how to make magic or have a magical object? Why? Which magical object from the story would you like to command? Would it be more useful to have a knife that can cut anything except people, or a genie that could grant wishes?

7. The Wolf King can transform into human shape. Is this a power you find appealing? Which animal(s) would you like to be able to change into? Can you name other stories with shape-shifters? At which points in the story would it have been helpful for Jack and May to have this power?

8. The Magic Mirror is the powerful object at the center of the story. Discuss the symbolism of mirrors: reflection, seeing clearly, vanity, etc. Why do you think it’s considered bad luck to break a mirror? What do you think it means when Merriweather and the genie are imprisoned in the mirror?

9. May gives up her sarcasm to the imp in exchange for Jack’s freedom. How is her dialogue different without the sarcasm? Do you like her better? Is she less funny? Why is it funny when someone makes a sarcastic comment? Would you be able to talk without your sarcasm? What would you be willing to give up in order to save a friend?

10. Grandpa tells Jack that his curiosity “might just get you into some trouble someday.” Do you think that curiosity is a blessing or a curse? What are the dangers of being too curious?

11. Do you think that someone as evil as the Wicked Queen could really love her granddaughter? Can bad people have good feelings or do good things? Is the opposite true? Do good people sometimes do bad things? Can a truly evil person be reformed? How might that come about?

12. Were you surprised to find out that May’s grandmother was the Wicked Queen? How does it feel to find out someone is not who you thought they were? How does May feel? How might this kind of surprise add depth to the story?

13. There’s a tremendous amount of action in this story. Do you think it would make a good movie? Would you imagine it as an animated movie or a live-action film with special effects? Is there anything missing from the book that would make it a better movie? Is there anything in the book that you wouldn’t include in a movie version?

14. The knight tells Jack that the sword has the possibility for evil, but that it “can be used for great good, in the hands of the right person.” How do we know that Jack is the right person, especially when his father was a thief? When Jack says, “We’re going to win because we’re good, decent people trying to accomplish something noble,” do you believe him? Do they deserve to win because they are good and brave?

15. Why do you think the title of the book is Half Upon a Time? Can you suggest some alternate titles? The book’s sequel is called Twice Upon a Time. Does that give you any clues about the plot? What do you think will happen in the next book? Will Jack and May’s relationship get better or worse? Will things they’ve learned in the first book help them do a better job next time?


Guide written by Bobbie Combs, a consultant at We Love Children's Books.

This guide has been provided by Simon & Schuster for classroom, library, and reading group use. It may be reproduced in its entirety or excerpted for these purposes.


About The Author

Author Photo by Maarten de Boer

James Riley lives in Virginia. He is the New York Times bestselling author of the Half Upon a Time, Story Thieves, Revenge of Magic, and Once Upon Another Time series.

Product Details

Raves and Reviews

Half Upon A Time has it all--voice, charming fairy tale characters with a twist, hilarity, and an adventure-filled plot.

--Bookinistas Blog

The first character we meet in this tale is Jack. But he is not the fairy tale Jack of Beanstalk fame. No, that Jack was this Jack’s father; and this Jack hasn’t seen him since that famous encounter with the giant. Living with his grandfather in the shadow of his father’s reputation as a thief, Jack is a different sort of hero. His education is devoted to learning how to save a princess, since that is the only way to escape his life as a peasant. Unfortunately, Jack doesn’t seem to be very good at it. He alone, of all the village boys, has failed his princess-saving test. Again. Still, that hardly seems to matter when a princess named May unexpectedly drops into his life. Her grandmother is missing, and she needs Jack’s help to save the old woman. Before you know it, Jack is facing witches and wolves, taking on giants and dragons with the best of them. Along the way, he and May pick up a dainty companion (a fairy), a noble companion (Prince Phillip) and a scary companion (the Wolf King). A host of familiar fairy tale characters appear, including—but certainly not limited to—Snow White, Merriweather, Malevolent, Red Riding Hood, the Wicked Queen, the Huntsman, the Seven Dwarves, and Rapunzel. James Riley’s novel is more a re-imagined and greatly embroidered fairy tale than it is a fractured one. “Quick-paced” is an understatement, as our heroes move swiftly from one danger to the next, with hardly a breath in between. The only disappointment is that all of the bad guys get away—but there’s pleasure in that, too, as it means we’ll get to see May, Jack, and Phillip track them down to set things right in a much-anticipated sequel. Highly recommended. -

RILEY, James. Half Upon a Time. 388p. CIP. S & S/Aladdin. 2010. Tr $15.99. ISBN 978-1-4169-9593-7; ebook $9.99. ISBN 978-1-4169-9595-1. LC 2010012714.

Gr 5-9–In his twisted fairy-tale world, hapless young Jack fails his princess-rescuing test, but fate gives him another chance when a circle of blue fire deposits May, wearing a T-shirt that reads “Punk Princess,” into his cottage. Jack recognizes her as a true princess and they set off on a quest to find her grandmother, Snow White. Joined by super-smooth Prince Phillip, and staying just ahead of the giant green Huntsman, they journey to the Black Forest, ride the wicked wolf’s back, release a genie when they break Red Hood’s magic mirror, and spend time in the dungeon of a fairy queen before finding Snow White and seven dwarfs in the Palace of the Snow Queen. Jack is perennially clumsy, and May has a quick, sharp tongue until she trades her sarcasm to save Jack’s life. Snappy dialogue, fast-paced action, unexpected twists, and the inevitable conflicts of a threesome made up of two teenage boys and a pretty girl make this an enjoyable read. A whirlwind ending upsets everything, setting the stage for a sequel.–Kathleen Isaacs, Children’s Literature Specialist, Pasadena, MD

- School Library Journal March 1, 2011

Awards and Honors

  • NCTE Notable Children's Books in the Language Arts
  • Sunshine State Young Readers' Award List (FL)
  • Mark Twain Award Final Nominee (MO)

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