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Old School Wednesdays Readalong: Jackaroo by Cynthia Voigt

Old School Wednesdays is a weekly Book Smuggler feature. We came up with the idea towards the end of 2012, when both Ana and Thea were feeling exhausted from the never-ending inundation of New and Shiny (and often over-hyped) books. What better way to snap out of a reading fugue than to take a mini-vacation into the past?

Old School Wednesdays Final

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In March 2013, we asked YOU for your favorite old school suggestions – and the response was so overwhelmingly awesome, we decided to compile a goodreads shelf, an ongoing database, AND a monthly readalong/book club.

This month’s OSW Readalong pick is Jackaroo by Cynthia Voigt.

For every readalong book, we’ll structure this a little bit differently than our usual Joint Review fare – first, we’ll give our (brief!) opinions regarding the book, then we’ll tackle some discussion questions. Finally, we’ll ask YOU to join in.


Jackaroo Jackaroo (new)

Title: Jackaroo

Author: Cynthia Voigt

Genre: Historical, Young Adult

Publisher: Atheneum Books
Publication date: First published 1985
Paperback: 368 pages

“False, they were all of them false, the stories; as false as the stories of fairies dancing in moonlight glades on Midsummer Night.”

But they served a purpose. In a distant time and far-off kingdom, life is hard. People don’t have enough to eat, and winter is upon them. There’s little that offers hope, and many turn to the legends of Jackaroo — the masked outlaw hero who rides at night giving aid to the helpless and coin to the destitute — for solace.

Gwyn, the Innkeeper’s daughter — sensitive, industrious, and independent — is too practical to believe such tales. But when a snowstorm forces her and a young Lordling to seek refuge in an abandoned house, Gwyn wonders if perhaps she has been too cynical. Hidden away in an old forgotten cupboard, Gwyn discovers a package — a cloak, a mask, a sword….Jackaroo? Could the stories be true?

Stand alone or series: First in the Jackaroo series

How did we get this book: Bought

Format (e- or p-): Ebook


Thea’s Take: WOW. I was not sure what to expect when I started Jackaroo – I’d never heard of the book before, and I didn’t think I’d ever read Cynthia Voigt before (this actually turned out to be false – I’ve read a few of her books before, but completely forgot! More on this in Question 4 below). All I knew going into Jackaroo was that the book was some kind of variation on Robin Hood/Zorro, with the legend of a masked vigilante protecting the common people from the rich, the cruel, and the corrupt. I didn’t know that this would actually be something akin to a hero origin story; nor did I expect this to be such a quiet and beautifully written book, with a richly detailed world and one hell of a protagonist.

In other words: Jackaroo took me by surprise, and I loved it.

Ana’s Take: I have to echo Thea’s thoughts here – I’ve never read Cynthia Voigt before and didn’t know what to expect from Jackaroo. And it really surprised me in a good way for its quietness, the strength of its protagonist and the story itself. I have a few “buts” but overall, I really liked it too.

Discussion Questions:

1. Jackaroo tells the story of Gwyn, the Innkeeper’s daughter, and her coming of age from willful young woman to donning the mantle of Jackaroo. What did you think of this origin story? Was it believable in your opinion?

Thea: I loved this origin story; I found it both clever in the way it draws on older tropes and refreshing in its quiet simplicity. Gwyn, our heroine, is the daughter of the village Innkeeper – compared to many in the village, Gwyn lives what seems to be a charmed life. Her father is prosperous and has several holdings, and the steadily increasing taxes levied on the commoners by the Lords of the land are painful, but affordable for the relatively affluent family. In fact, Gwyn has FOUR gold coins for her dowry. Sure, she has to work hard at the Inn, cleaning and serving and caring for the garden and the horses in good hard labor, but compared to the rest of the townspeople? Gwyn lives a good life.

That said, Gwyn is not happy with her quiet life, and she certainly isn’t eager to marry anyone. Although she can’t quite put it into words (she’s not a very introspective character), Gwyn is frustrated with her life, with her coddled younger brother, with the quiet status quo. Her origin story is one fueled by this pent up frustration, and her desire to act while others do nothing. And… I loved that. I love that Gwyn’s story is a very subdued one that unfolds slowly, and that from the moment she discovers Jackaroo’s boots, mask and feathered cap that it’s only a matter of time before she dons the cowl – fueled by a unique combination of empathy for others and her caged-in frustration.

Most of all? I love that the figure of Jackaroo isn’t glorified or melodramatically turned into some kind of legendary badass. I love the actual story behind the mantle, the people who have and will wear the mask, and Gwyn’s understanding that being the hero of legend comes at an incredible cost.

Ana: I agree with everything that Thea said about Gwyn and won’t repeat the same points. Instead, I’d like to dwell on the Jackaroo figure and how that was incorporated into the story.

In the book, Jackaroo is a legendary figure, very similar to Robin Hood. Everybody knows the stories about his exploits. It’s a theme that runs through the story and appears in many ways. It speaks to the nature of storytelling as well as to the building of legendary figures and to the need of heroism. With regards to the latter, I loved how the idea of Jackaroo as a hero was developed over time, depending on the needs of those who tell the story. I loved the actual story about those behind the figure and how that was used in the story itself, mantle that was donned by different people from all social strata.

2. Let’s talk more specifically about Gwyn, the main character of this book. How did you feel about this particular heroine? Love her? Hate her? Was she too exceptional or special?

Thea: I loved Gwyn, and I love the way the synopsis of this book paints this heroine: “sensitive, industrious, and independent.” Yes, this is all very true. Gwyn is sympathetic to the pain and suffering of others, she’s hard-working, and she questions the mores of her world. I’m not talking about anachronistic, typical YA heroines that feel far too contemporary for the eras they supposedly inhabit – I mean that Gwyn questions things within the context and framework of her society, and her challenges to the accepted order of things feel genuine without making her seem too contemporary. As to the question of exceptionalism, I can understand why Gwyn might be read or interpreted as such. In my opinion? I don’t think she falls into that trap of being infuriatingly Super Special. Gwyn does not want to marry, but she’s not the only woman who does not marry in her society; she’s strong and capable, but so are so many of the other characters Gwyn interacts with. What distinguishes Gwyn is her combination of sympathy and gumption, but that also felt well-developed in my opinion. And, while she’s a character with so many praises, she’s also not perfect – she’s headstrong to a fault (although she owns up to her mistakes), she’s jealous of her younger siblings (even if she doesn’t admit it to herself), and while she’s wonderfully observant about some things she is a complete dolt about others.

Suffice it to say, I am a big fan of Gwyn’s. (The only thing that felt a little heavy-handed to me was Gwyn’s immediate aptness at reading and writing, but this is a minor nitpick.)

Ana: I loved her. I loved her viewpoint and how it functioned to astutely observe the mores and the stratification of that society. It’s funny how Gwyn’s narrative is not exactly introspective in a way that rehashes her feelings and thoughts in so many detailed words but one that shows more than tells how she feels and thinks. It’s a story that is full of angst and frustration without being angsty and frustrating if that makes sense at all?

I agree that she is not “exceptional” in the way that she questions or feels about things. There were other characters who did so as well and who choose their own path despite the consequences. Which is why I felt that the ending was so disappointing but more on that later.

3. What about worldbuilding? Jackaroo‘s world is a model of historical/medieval-ish western Europe, with strict dividing lines of wealth, bloodlines, and specific gender roles. What’s your take on this setup?

Thea: The actual world of Jackaroo is pretty standard historical fare – western medieval-ish setting, women in diminished societal roles, the poor very poor, and so on and so forth. That said, Jackaroo has a level of detail and authenticity that is hard to find in current YA (or current historical novels in general). Most often, the historical setting is glamorized or viewed from the perspective of a beautiful or high-born main character – sympathetic princesses, brave and strong noblemen, etc. I very much appreciated the far less glamorous approach in Jackaroo, with its focus on daily life for the commoner and the disenfranchised. Even though Gwyn is the daughter of a respected Innkeeper, and compared to others is relatively well-off, her life is a hard one (and a far cry from the life of a Lord, as we see with her interactions with a particular mapmaker and his young noble son).

My biggest gripe with this traditional type of world setup – other than it being so freaking familiar, of course – is that often the gender roles or other societal norms aren’t challenged. I am very, very pleased to say that Jackaroo questions, provokes, and examines the dividing lines not only between men and women, but also the rich and poor and legend and tradition. I like that very much.

Ana: I am conflicted about this one.

Although I do think those roles and societal norms are challenged, I think ultimately within the story, those were still reinforced because of how the story ended? Gwyn spent most of the novel challenging the way that she had few choices and the way that marriages are arranged but in the end she still ends up married because she had no choice. Similarly, although the story shows the awkward, fraught divide between the rich and the poor, the Rich Character is still the one with All the Answers and who proves to be Good? I do not want to dismiss the fact that the book does provoke and challenges and does it so really well.

But that ending left a bad taste in my mouth. It is all the more strange because it was the ending that I was rooting for (with a measure of freedom for Gwyn, and I loved who she ended up with very much) but it was the how she got there that gives me pause. I wished Gwyn had reached that point on her own terms and not because she didn’t have any choice at that stage. I hate that she arrived at the conclusion that her romantic interest was the right one for her only after it was pointed out to her. That said: it worries me that the fact that I am saying this, implies that stories of people who have fewer choices, who are not privileged, and have to deal with what life throws at them and find happiness any way they can are not important, because obviously they are.

I said I was conflicted. Really curious to see what everybody thought of it.

4. Cynthia Voigt is the author of many novels (seriously, look at all of those books). Have you read any of her books before? Will you try any others or continue with this series? If you have read the series already, do you recommend us to keep on reading?

Thea: Earlier in this discussion, and when I started this book, I thought I hadn’t read any Cynthia Voigt books before. This actually turns out not to be true – I have read a few of Voigt’s books when I was a tween and teen. The one that jumps out at me the most? Izzy, Willy-Nilly – the story of a high school girl who is in a terrible car accident that costs her a leg, and leads her to a very different type of life. Man, that book was deep and hard to read, but I recall reading it and enjoying it for its rawness and for the friendship between the two main characters. (I also remember David and Jonathan, and, vaguely, Homecoming).

As for the rest of the books in the Kingdom series? HELL YES I will be reading them. I also will be reading Voigt’s 2013 release, Mister Max very soon.

Ana: I haven’t read any Voigt before but I have Mister Max soon. Thea, joint?

And I want to continue with the Kingdom series!

5. What is your favorite thing from this book? What weren’t you enthusiastic about?

Thea: I think my favorite thing about Jackaroo is Gwyn – hands down. I also very much appreciated the relationship between Gwyn and her younger brother Tad, plus the other young man she’s shored up with for a while (the young Lordling). I loved the prickly interactions with her bitter yet loving mother, her steadfast father, and the surprise appearance of another family member late in the book.

Of course, there’s also the romance aspect. It’s a bit The Princess Bride – and while I was a little dissatisfied with the way everything ends, I did love the backburner romance between Gwyn and the solid, quiet Burl.

Ana: I loved Gwyn above all but also really appreciated the quietness of the novel overall. I also loved the take on legends and stories and their importance in creating a myth that was known to everybody.

Like I said, I didn’t like the ending even though it was the ending I wanted.


Ana: 7 – Very Good

Thea: 8 – Excellent


Now over to you! Please feel free to engage with the questions (and our answers), come up with your own talking points, and/or leave links to your reviews!

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  • SaraHope
    September 25, 2013 at 2:12 pm

    Squee, I’m so glad this was chosen and enjoyed. I must confess I did not reread it in time for this OSW, but I’m putting it on the re-read list. Of the Kingdom series I’ve only read Jackaroo and On Fortune’s Wheel, so I plan to re-read those and continue on to the other two books after.

  • de Pizan
    September 25, 2013 at 3:30 pm

    Jackaroo and On Fortune’s Wheel are probably two of my favorite YA books ever. I’ve never done a huge amount of re-reading (too many books too little time), but these two are in a small group that I have read repeatedly over the years. I love Gwyn, and I love Burl. I see what you’re both saying about the end, but I think it’s a decision that Gwyn would have come to in the end eventually, even if circumstances were different. It just would have taken her longer to get there.
    Cynthia Voigt isn’t a flashy author, but I think she’s a fantastically consistent one that you can almost always count on to deliver (I think I’ve only read one book by her that I actually disliked, which was Tree by Leaf), she especially delivers when it comes to characters. I’d recommend (re)visiting the Homecoming series also, especially Homecoming, Dicey’s Song and The Runner.

  • Noelle
    September 25, 2013 at 4:50 pm

    I loved The Kingdom series when I was younger and revisited them earlier this year but had to stop at book 3 as I couldn’t find a copy of On the Wings of a Falcon. I think there’s still one on my childhood shelves 8 states away so one day I’ll track it down again! I was unaware there was a book 4 so I’m excited about reading that for the first time. I’m so glad you enjoyed Jackaroo! I just adore Cynthia Voigt.

  • Juan Pazos
    September 25, 2013 at 5:39 pm

    argh! I’m not even halfway!! 🙁

  • Kate Karyus Quinn
    September 25, 2013 at 9:27 pm

    I read this when I was a teen (along with everything else Cynthia Voigt had written and that my library had available) and when I saw you’d picked it for your read-along, I was pleasantly surprised to find a copy of it on my bookshelf that I had bought at a library book sale a few years ago and then forgotten all about. At the same library sale I also bought a copy of On Fortune’s Wheel which I also read as a teen, although I have re-read OFW many times since then and it is a definite favorite of mine, due in so small part to the romance plot that is full of everything I love. Anyway, it was great hearing your thoughts and I am so glad that Old School Wednesdays brought this book to the top of my TBR pile. I will definitely be following this up with On Fortune’s Wheel very soon!

  • Jana
    September 26, 2013 at 12:41 am

    I first read Jackaroo quite a few years ago (maybe 15…it’s been a long time), and then re-read it back at the beginning of this year because a kind relative gave me books 1-3 of The Kingdom for Christmas. (How unfair is it that The Wings of a Falcon is out of print??) Honestly, in the interim, Jackaroo hadn’t lost any of its appeal for me. Gwen is still a great character, the various circumstances of the plot come together well–though I agree, she masters reading and writing far too quickly–and even though the ending is a little too neat, it was still satisfying. In particular, I liked that while Gwen is a unique individual, she isn’t one of the “special snowflakes” that seem to have overtaken modern YA novels. She’s flawed, she makes mistakes, and she strives to do better, but she’s neither perfect nor a paper doll. I long for the pre-Twilight days of my youth… Ah, well.

    I like On Fortune’s Wheel and The Wings of a Falcon as much as (and sometimes more than) I like Jackaroo, but I haven’t gotten any farther than the first few chapters of Elske because it’s a little weird and intense. Is there anyone who’s read all four Kingdom books who can tell me if it’s worth getting through the awful stuff?

  • de Pizan
    September 26, 2013 at 12:57 am

    Jana, Elske is in a very different vein than the other books. The beginning and towards the end (a brief battle) has some intense stuff, but once you get past the first few chapters, it does get better and the whole book is definitely not all like that.

  • Eliza
    September 26, 2013 at 9:40 am

    I love Cynthia Voigt’s writing, though until OSW I only had read her Tillerman Cycle books, of which Homecoming is one of my absolute favorite books and Dicey one of my top heroines. I was really glad to expand my reading into some of her other books and definitely will read the other books in the Kingdom quartet. For those of you who’ve read the quartet, is my understanding correct that while each book takes place in this world, each one is a stand alone?

    I really enjoyed all the characters and how well drawn they are. Like others have mentioned, I particularly loved that Gwen wasn’t the perfect little flower who is beautiful, every male falls in love with her on sight, and she can do anything perfectly the first time without any effort. She messes up. For example, even though she and the Young Lordling spared with wood “swords”, when it came time for her to use a real one, she was completely terrible at it. Just like anyone would be in a real sword fight without any training. I kind of disagree on the concerns that she learned to read and write so quickly. Once she started learning, she practiced at it every day and she’s bright. I think it was enough for her to grasp a rudimentary knowledge and that’s all I think she had. Though I’m sure she improved over time now that she was living in a house with a library.

    I had a different read than Ana about the ending. I think she got to marriage on her own and it was something she wanted. If it wasn’t, I don’t think she’d have agreed to it and would have gone on to be a servant. I love that she and Burl fell in love slowly and that it took her a while to realize that she did love this very good man. I think her hesitation in agreeing to marry him was twofold: (1) up until that point she didn’t think it would be a possibility that they would end up together. They would separate with Burl going back to her parents’ inn and she would be a servant in the Earl’s household; and (2) she didn’t want Burl to be forced to marry her and take away his options of going back home to the inn and having his own life. I don’t think she knew that he loved her until they discussed it.

    One of the other things I loved about the book is the realistic portrayal of the class system and how strict the class lines are. Even stranded in a tiny cabin together the lines were still maintained for a long time between Gwen and the Young Lordling. So much so that even when they began to break down it was only bent so far (e.g., she still waited on him, ate separately from and after him and on the floor never at the table). When they rejoined society, the roles immediately fell back in place. It would have been unrealistic for anything else to have happened.

    An enjoyable book and one I wouldn’t have read without OSW. So thanks!

  • de Pizan
    September 26, 2013 at 12:52 pm

    Eliza, you are correct, each book takes place in this same world, although perhaps in neighboring kingdoms/countries, although there is always cross-over into this kingdom. They are stand alone, but there is a connection between them all, which could be a possible spoiler I suppose for those that want to discover it themselves, so stop reading now if you don’t want to know.

    Each book features a character who is a granddaughter of the woman from the previous book. So On Fortune’s Wheel has Gwyn’s granddaughter in it. I think that would make the woman in Elske Gwyn’s fourth great-granddaughter, if I did my generations right.

  • Jana
    September 26, 2013 at 6:25 pm

    Thanks, de Pizan! Maybe I’ll see if my local library’s got a copy of Elske that I can snag. I won’t be sure if it’s worth the investment of a purchase unless I can get past that awful beginning.

  • Eliza
    September 26, 2013 at 9:58 pm

    Thanks, de Pizan. I love that twist and it makes me want to read the remaining books all the more. My library has them, so I’m in luck. Now I just have to fit them in with all the others on my TBR.

    Isn’t Homecoming one of the best? I keep hoping it will be a OSW pick so we can discuss it and the awesomeness of Dicey.

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