Learning Day: Mr. Head Mistress (Patreon)

There was a period in the late ’90s when Disney executives were really greenlighting every weird idea. Someone walked into Disney corporate and said, “You know how in Mrs. Doubtfire three children are tricked into being cared for by their loving father? Well, what if we do that but with a convicted criminal in an all-girls school instead?” A man who just got out of prison sneaking into an all-girls school sounds like the plot of a highly produced and highly problematic ’70s porn, but Mr. Headmistress definitely aired on The Wonderful World of Disney.

Harland Williams, the lead actor of Mr. Headmistress, has had one of the most interesting careers I’ve ever seen. He found consistent work in both very adult comedies like Freddie Got Fingered, Sorority Boys, and Half Baked, while simultaneously starring in Disney movies. The same year he made Mr. Headmistress, he also had a role in There’s Something About Mary. The same year he voiced a giraffe in Madagascar: Escape 2 Africa, he was also in Bachelor Party 2: The Last Temptation. Not many actors are allowed to do both, but I guess Harland Williams is the only one who has the range.

In the last few years, he’s settled into the Disney lifestyle, creating a successful Disney Junior show for them called Puppy Dog Pals, which follows the adventures of two pug puppy brothers. He voices Bob, the pugs' owner. This is a far cry from his portrayal of a psychopathic hitchhiker in There’s Something About Mary or the convict-turned-drag queen school marm in Mr. Headmistress.

“It’s not an all-girls school anymore.” Was the tagline for this movie that could have easily been rated R with a few minor tweaks, and Harlan Williams could still have played the main character. It’s probably one of the few Disney movies that opens in a prison, where we meet the Disney Princess of this film, a convict named Tucker. He’s selling hot dogs while all of the other prisoners gather around a televised boxing match. He stuffs the cash from his sales into a sink pipe so the warden won’t find it.

Tucker is called to the warden’s office, where we learn he’s about to be released and the warden doesn’t have high hopes that he’s reformed, which is correct because Tucker has already stolen some license plates he plans to sell to people with stolen cars. The warden says, “It’s amazing how you resist my three proven methods of reform: incentive before discipline, always lead by example, and always be yourself.” Gee, I wonder if those will somehow come back around? Probably not.

Tucker is released from prison and immediately met by two guys who say he owes them money. A chase ensues, and Tucker ends up on a train, hiding in a train car with a cranky stereotypical British woman. Supernanny wasn’t streaming yet, but she’s a Supernanny or a Miss Trunchbull. The kind of woman whose face says being mean to children is my number one joy in life.

She ends up getting knocked out when Tucker pulls the emergency stop on the train, so Tucker steals her clothing and wig and does a full beat of her makeup in the thirty seconds before his business associates find him on the train. His plan is to make a quick escape, but he looks so much like Naomi Bascombe, the woman whose clothing he took, that the man who was supposed to pick her up immediately pulls Tucker into his car. He’s been a woman for two seconds, and he’s already been kidnapped by a man. He’s terrible at this!

Naomi Bascomb is set to become the headmistress at the Rawlings Academy, a girl’s boarding school that isn’t quite a reform school, but maybe it should be? All of the girls there have been kicked out of other schools, have bad grades, and are bad at sports. How they filtered all of the loser girls into one boarding school is not revealed but it might as well be called the Daddy Warbucks School For Rich Loser Daughters.

All the pupils at the Rawlings school are delinquents, but in a very charming, Disney-movie way. They immediately want to prank Tucker out of a job, not because they think he might be a convict who gave the real Naomi Bascomb a head injury and stole her hair. That was already the plan before their, clearly a convict in stereotypical mean British woman’s clothing, Headmistress arrived. Tucker plans to take off immediately, but he learns there’s a major donation coming to the school from a pervy old man with the last name Rawlings if the girls can raise their grades, and the $500,000 check will be turned over to him. His eyes immediately become big dollar signs, and suddenly he is the headmistress of the boarding school.

Only someone with the audacity of a man would be like, “Even though I’ve never tried it, I feel like there’s a pretty good chance I’m the best headmistress that has ever lived and I’ll finally be able to get through to these girls.” He focuses his efforts on the clear leader of the Rawlings Academy girl gang, Beryl. Her problem is that her parents hate her, which you can tell because they named her Beryl. She’s also a classic Disney Princess because she has a dead mom and an evil stepmother, and she’s like Tucker because she sells pizza to the girl while they watch TV in her room and hides the profits in a sink pipe just like Tucker did in prison.

There are a lot of "boarding school is just like prison" jokes, which might have turned me into a delinquent. This Disney movie made committing fraud look cute as hell. Please hit me up if you need someone to do fraud with. I think I’d be good at it.

Anyway, Berly tells Tucker the girls want a dance with boys in exchange for getting their grades up. Subconsciously remembering the warden's rule of incentive before discipline, Tucker agrees to throw the girls a dance. This enrages Katey Sagal, the second Miss Trunchbull of the film. She wanted to be the school's headmistress but was passed over for Naomi Bascomb, and now she’s horrified to find a headmistress being (GASP) nice to the children. This is disgusting to a woman with a decorative pyramid of child beating rulers on her wall.

Tucker lies about the dance. He gets a con man friend of his to come and pretend to be from a military academy full of horny boys who can’t wait to dance the girls' brains out. They are so thrilled that they stop being stupid and raise their grades by forty percent. Tucker thinks this will get him that promised check, but the pervy old man who is clearly kind of into him is like, “Well, what if they also won a field hockey game?”

At this point, Tucker has been at the school for, I would assume, one week. I’m not sure how long the real Naomi Bascomb is meant to have been passed out in the bathroom of her train compartment, but she emerges and begins to rampage across the countryside. Since Tucker has left her with no money or cell phone, it might take her a while to reach Rawlings Academy, but not long enough for Tucker to lead the girls to a field hockey victory, I would imagine.

So now we’ve got two, maybe three, ticking clocks: the real Naomi Bascomb coming for Tucker, child-hating Katy Sagal out to get him, and the original two criminals. Tucker remains unconcerned. He’s got girls to teach field hockey.

At first, the girls are mad at him because the boy's dance never materialized, but after some field hockey lessons where he leads by example and a heart-to-heart with Beryl where they bond over their terrible fathers, the girls are ready to be good at field hockey now. All this school needed was for a man to run it, and suddenly it’s way better! Criminals should be allowed to run all girls' boarding schools is the moral of this story.

All of the people out to get Tucker converge on the big field hockey match, and Tucker’s scheme is outed, but not before the girls win the match, and with all of the conditions met, Tucker is handed the check for five hundred thousand dollars. He’s free to finally take off those inch-thick support hose and escape the bonds of British womanhood. Except he doesn’t! He’s fallen in love with the school and can’t come to steal the money. Aw, those other criminals are going to cut his thumbs off.

The girls protect Tucker from his former accomplices by pelting them with field hockey balls until the police show up to arrest them for having Tucker's stolen license plates in their car, and I guess, also for attempted murder. Tucker is free to go, but this movie could only end one way. They make him the Headmaster of the school. I’m not kidding. They make the convict, who was one good vibe away from stealing 500K, the top job in the school. I thought maybe they would make him a teacher or something, not put him in charge of the whole thing.

The movie ends with Tucker throwing the promised dance with real boys for the girls to dance with. He briefly considers stealing a fancy silver salt shaker, then realizes he doesn’t have to. He’s gotten a real job, probably a pretty well paying one, by being his true self. Also, a little bit of fraud. This ending feels like it was written for the generation of parents who didn’t understand why their children couldn’t just get a job by walking into the CEO’s office and asking for one. If you really want to be the headmaster of an all-girls boarding school, why not just simply knock out the old one, steal her wig, and impersonate her? That’s how we did it in my day.

You might be thinking this movie was surprisingly chill about the whole man dressing as a woman thing. If they made it today, Tucker would be part of the Republican platform in three seconds flat. A convict dressing as a woman to become headmistress of an all-girls school is exactly what the Democrats want! They do mention that Tucker still uses the men’s restroom at the school and tells everyone it’s because no one is ever in there and he “wants privacy to tinkle,” so the bathroom thing was a big deal for idiots even back then, I guess. He can be the headmistress of the school, but we draw the line at listening to the schoolgirls' piss. Thanks, Mr. Disney. You’ve saved us again!

This article was brought to you by our fine sponsor and Hot Dog Supreme: Alex Knollenberg, who also went from slangin prison dogs to being the headmistress of an all-girls boarding school, but nobody ever made his movie. Some guys get all the luck.

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