Matilda, Annie, and the Generation Gap

“When I’m stuck with a day
That’s gray, and lonely
I just stick out my chin
And grin, and say, oh
The sun’ll come out tomorrow
So ya gotta hang on ’till tomorrow
Come what may”


“Just because you find that life’s not fair, it
Doesn’t mean that you just have to grin and bear it
If you always take it on the chin and wear it
Nothing will change
Just because I find myself in this story
It doesn’t mean that everything is written for me
If I think the ending is fixed already
I might as well be saying I think that it’s OK
And that’s not right”


I never had much of a relationship with any version of Matilda before the recently released film Matilda the Musical now on Netflix. Despite being a Roald Dahl fan as a kid in the 80’s/90’s, I somehow never read the original story. As a result, I didn’t make an effort to see the 1996 film, which I might have felt a little too old for at the time. The 2011 stage musical, which the new film adapts for the screen, never made it to my home of Tucson on its national tour. So despite a passing familiarity with the story and plenty of opportunities to connect with the material through my 38 years, I went into this new version of Matilda the Musical as a mostly blank slate, with my 4.5-year-old son beside me.

It instantly became our new household obsession. We’ve watched it four times in the last nine days, our son demands the soundtrack to be played at every opportunity, and he requests that I sing its climactic number, “Revolting Children,” for his bedtime song every night. It has spectacularly catchy and clever music, kinetic and exciting choreography, gorgeous production design, excellent performances from both the kids and adults in the cast, and a story that speaks to universal values of justice and equality.

It also has a lot of parallels to the iconic musical Annie, which were brought to the forefront of my mind yesterday when by coincidence my wife and I had tickets to see the current national tour. Our son asked to watch Matilda the Musical yesterday morning and our tickets for Annie were in the afternoon, and the juxtaposition of the two similar musicals in the same day had my mind reeling. Unlike Matilda, I have a long relationship with Annie, which was the first musical I ever saw on stage. My mother and grandmother took me to a performance as a young child, and it ignited my love of musical theater. Those first three dynamite songs (“Maybe,” “Hard Knock Life,” and “Tomorrow”) combined with the strong pull on the heartstrings that comes from Annie calling Sandy and having him come to her captured my imagination. We would have taken our son to Annie yesterday, because he would have loved it, but when the tickets were purchased almost a year ago we didn’t know whether he’d be old enough. (As it is, his first musical theater experience was The Lion King, which isn’t a bad way to go either.)

I love Annie. Its songs are almost all iconic for a reason, even as I notice things now as an adult that I didn’t notice as a kid. For instance, Annie opens with its three best songs in the first 20 minutes, and is forced to reprise them throughout while the remainder of the still-great songs fade in comparison. Still, I sang “Tomorrow” to my son when he was an infant, and I look forward to introducing him to Annie the next time it comes through town. But after watching it and Matilda back to back yesterday, I’m much happier to have my son singing along to Matilda (as he currently is while sitting next to me as I type and we watch it again) than to Annie, despite my love for both.

The Annie vs Matilda dynamic seems to perfectly speak to the generation gaps in today’s society, particularly between Boomers and Millennials. The two musicals, so superficially similar with their plucky young female protagonists, were written for very different audiences in very different times and have very different things to say about children, their places in society, and how they should act. Annie and Matilda, the characters, both start in awful circumstances with evil, neglectful, abusive guardians, come face to face with injustice and inequality, and end their stories in the care of loving, supportive parent figures. Their stories, however, couldn’t be more different, and those differences can tell us a lot about the disconnects between Boomers and Millennials.

Annie first debuted onstage in 1977, with music by Charles Strause, lyrics by Martin Charnin, and a book by Thomas Meehan. It’s based on the “Little Orphan Annie” comic strip which began in 1924 and which spawned film adaptations and a radio show before it made its way to the stage. Its high point of popularity was during the Great Depression and before World War II. As such it wasn’t the childhood staple of Boomers as much as it would have been for their parents, though it would have been regularly published in newspapers during Boomers’ youth. 

By the time of the Annie musical, Boomers would have been in their mid 30s, many with Gen-X children of their own to watch it with. The 1930’s setting of the musical, with its hardships of the Depression and the looming prospect of war, was intended to resonate with adult audiences who had lived through their own hardships of the Nixon era and the horrors of the Vietnam War. Its message of optimism and unity in that older era spoke to the need for optimism to try to lift the national mood in the 70’s. I can imagine that message speaking to parents of children who hoped their kids would grow up in a more positive situation.

Matilda, the novel, was published in 1988 and many Millenials doubtlessly grew up with either the book or the popular 1996 Mara Wilson film. By the time the musical debuted in 2011, with music and lyrics by Tim Minchin and a book by Dennis Kelly, those Millennials had grown into young adults of the sort likely to go see a stage version of a story they loved as kids. And now with the movie another decade later, many of us now have children of our own to introduce to the story. But what speaks to us is very different from what spoke to parents of young kids in the 1970’s.

What is Annie’s defining characteristic? What motivates her? How does she follow that motivation and where does it lead her? Annie is primarily defined by her goodness and her sunny optimism. She looks after the other kids in Miss Hannigan’s orphanage, helping them when they wake up crying in the night. She dreams of finding her parents, who left her a note and a locket, and she runs away determined to do so. She has an irrepressibly positive attitude, as we hear in her signature song, and every move she makes is rooted in that attitude.

Matilda’s defining characteristics, on the other hand, are her genius brain and her sense of justice. Her motivations are to learn and to fight for fairness. These lead her to be a troublemaker, to challenge authority, and to ask questions of those in charge. Both girls try to protect their friends and those who are oppressed or down on their luck, but they do it in completely different ways. 

Annie shines her positive light to inspire the grownups to be more like her, good and kind. She brings together Republican billionaire Oliver Warbucks and Democrat president Roosevelt (who was hated by “Little Orphan Annie” creator Harold Gray) to catch the bad guys, create the New Deal, and eliminate the Hoovervilles like the one she passes through early in the play. Unity, honesty, and benevolence save the day in Annie’s world.

Matilda inspires those around her as well, but she doesn’t waste her time trying to appeal to the better nature of those in authority. Instead she uses her powers to destroy the tool of Miss Trunchbull’s oppression (the nightmarish “Chokey” dungeon), lends her bravery to her peers so that they stand on their desks in open rebellion against their headmistress, and frightens and then flings her bodily (at least in the new film) from her seat of power. Her righteous anger about the state of things makes her fight back in a way that’s completely foreign to the world of Annie.

The musical Annie treats its children like plot devices. Sure, Annie is a great character, with pluck and wit and charm, with great songs to sing. She sees the good in the world and helps things to turn out better in the end. But other than running away at the beginning she doesn’t actually do much other than be a positive presence. She melts Daddy Warbucks’ heart and inspires Roosevelt and his Cabinet, but she doesn’t drive the plot once Warbucks takes her in. Miss Hannigan’s and Rooster’s plot comes and goes without any particular input from her. Warbucks’ assistant, Grace, first notices the scam and it’s foiled due to Warbucks and his government connections to Roosevelt and the FBI. A wealthy benefactor having his attitude changed just by Annie’s mere presence is all it takes to save the day.

Matilda treats its children like humans, with agency, skills, and power. Matilda, the character, drives the plot. She’s thrown from one awful situation in her home into another awful situation at Trunchbull’s school. She bonds with her schoolmates and helps to protect them when they’re in danger. She uses her cleverness to foil Trunchbull’s plans, and when injustice happens she dares to shout, “No!” in the face of those in charge, inspiring everyone around her. As her power grows and Trunchbull’s rage to match it, she uncovers the headmistress’s evil past, tears down the Chokey, exposes Trunchbull’s crimes, and eventually drives her away for good. All of the positive change happens because of the children, and not Matilda alone. She doesn’t lead the final revolt, though her stands earlier in the film helped inspire the bravery of the others.

Annie and Matilda treat the systems we have to deal with completely differently. Annie sees its conflicts resolved by working within the system to find compromises between those with power to craft a New Deal. The massive amount of unhoused people are helped by being given jobs that will ultimately make one of the richest men on Earth even richer. The rising tide will theoretically lift all boats, and they’ll be well prepared to fight the enemy looming on the horizon, while the rich who never had to suffer any of the hardships of the common folk will continue to thrive. Matilda resolves its larger conflicts by ultimately tearing down the system, removing the unjust from power, and building something completely new. The evil headmistress is banished, the oppressive school is rebuilt into something completely different, and the neglectful parents are sent away. Matilda argues that sometimes there is no common ground, that those in charge who made things the way they are should be removed from power, and that the systems that enable abuses should be dismantled.

Even the good adults of these stories speak to very different values. Daddy Warbucks is one of the richest men in the world, a billionaire among millionaires, who isn’t in any way required to be kind or generous, but ultimately decides to be thanks to the goodness of his adopted daughter. His staff are all kind, good people, but they’re also presumably well paid with a generally benevolent boss in a time when those living in the Hoovervilles would probably do anything for their jobs. Can you imagine a popular musical today where the hero is a billionaire industrialist whose powerful connections help save the day?

Matilda‘s heroic adults are her teacher, Miss Honey, and the operator of the mobile library, Mrs. Phelps (not coincidentally, two women of color). Having a teacher and a librarian as the only two good adults in the story was a move that has only gotten stronger in the decade since the musical debuted, given how threatened our schools and educators, libraries and librarians are these days. Mrs. Phelps offers Matilda a refuge (though she does not know from what), an outlet for her stories and imagination, and an endless supply of knowledge through her books. Miss Honey is just as bullied by Miss Trunchbull as the students, as much of a victim of both the woman in charge and the system as a whole. Miss Honey admits after a question by Matilda that teachers are very poorly paid, and she is paid less than most. She lives in a rundown shack but has come to accept that, “it isn’t much but it is enough for me.”

In the opening number of act two (at least how the story is split on stage), “When I Grow Up,” Miss Honey even joins in singing with the children as they dream about being strong and brave enough to endure the challenges of the world. Miss Honey, relatable to many Millennial adults, still dreams of being those things despite already being an adult, as the system and those in charge treat her as if she is still a simpering child so that all she knows is fear. She is inspired by the children just as Warbucks is in Annie, but she doesn’t need to be inspired to goodness as she already has it within her (something common to the many teachers I know). Instead, she is inspired to have the bravery to fight back against the systems that have oppressed her and those like her, just as the children do.

As nice of a kid as Annie is, the Matilda of the musical is much more the sort of role model I would hope my son would emulate. That’s nothing against optimism, which I also believe is supremely important, but when faced with injustice I would always want my child to fight back, even if it means they have to be “a little bit naughty.” I’d rather have a child who is willing and able to tear down oppressive systems than one who only hopes and waits for things to get better. Many Millennials like myself would love to be Matilda, tearing things down and building something new and better in its place. But we’re more likely to be Miss Honey, quietly trying to do good and be kind in a world that is harsh and unfair. It isn’t much, but sometimes it’s enough or it is all we feel we can do. If we can’t be Matilda, then the best we can do is set up our children to be the fighters we wish we could be.

One of the most powerful moments in Matilda the Musical comes near the end but before Matilda’s final confrontation with Miss Trunchbull. She has discovered her telekinesis when she and the other children were finally pushed too far, when in her head “the noise becomes anger and the anger is light.” Miss Honey takes Matilda back to her shack for a cup of tea, and Matilda learns that Miss Trunchbull was responsible for the deaths of Miss Honey’s parents and her current awful situation. Matilda, resolved now to be proactive in the fight instead of just standing up in the moment, storms off in the rain, ready to do something. Miss Honey stops Matilda and warns her, “You need to be very careful. Miss Trunchbull is… capable of awful things.”

“I’m not scared of her,” Matilda replies.

“You should be,” Miss Honey tells her. “She’s dangerous.”

“So am I.”

Can you imagine anyone describing Annie as dangerous? Can you imagine Annie viewing herself that way? This exchange highlights one of the biggest disconnects of the generation gap in our age. Because the truth is, plenty of older folks do view children (and by extension youth, young adults, and basically anyone younger and more different than themselves) as dangerous. Millennials are used to being blamed by screaming editorials for everything from the trivial to the extreme, as if we’re ruining the world that was carefully crafted by previous generations out of spite or laziness. But while the young are dangerous, as Matilda understands, they’re only dangerous to the obstacles that stand in their way, the injustices and oppression that they see, and the systems and structures that create those things.

When you spend your life being told you’re a nothing and a burden and a waste, as Matilda and her classmates have been, you lose the respect and fear of those systems and structures that help to keep the young and the oppressed in line. That makes the young dangerous and powerful, and it’s why some of the biggest cheerleaders for Gen Z and their disregard for rules and tradition are the Millennials like Miss Honey. And I can only hope the next generation, like my son, are even further freed from those burdens and limitations society tries to set on them, because imagine what a generation of Matildas could create if they didn’t have to focus all of their energy on tearing down the walls built to hold them back.

Matilda inspires me to hope for the future, but not in the style of Annie, where the hope is that everyone will decide to be good and work together. Instead, the hope comes from the belief that the next generation, given the example of Matilda (and Newsies, and other works with similar messages) will fight and win in ways we couldn’t. Annie is an iconic and immensely entertaining piece of musical theater, but today its message of the power of optimism to bring about change merely by existing couldn’t hope to resonate with younger audiences the way Matilda will. (If you want a more challenging and rewarding story of optimism and its place in today’s world, I of course will point you towards Tomorrowland.) I will continue to push my son to be one of Matilda‘s revolting children: one who is dangerous, who won’t let a little thing like being little stop him, and who’s not afraid to get a little bit naughty.

“You mighta’ thought we were weak but we’re strong
Mighta’ thought we would break but you’re wrong
Because you finally pushed us too far
Now there’s no going back ’cause we are

Revolting children
Living in revolting times
We sing revolting songs
Using revolting rhymes
We’ll be revolting children
Til our revolting’s done
It is 2-L-8-4-U
We are revolting!”

-“Revolting Children”