What It’s About: Twenty years after graduation, an emotionally crippled writer is still hung up on Winona Ryder, a girl who was nice to him once. He returns to his hometown to give a commencement address and tries to put it in her.
Who It’s For: Emotionally crippled writers.
High school was not the easiest. Sometimes people were mean, sometimes I was mean, and I hadn’t yet figured out who I was or what I wanted. I did not have the best time in high school. Do you know who else didn’t have the best time in high school? Everyone. It's true for everyone, the end.
But people keep writing about their high school experiences like each one was a precious snowflake, and that it is only with the perspective gained from majoring in the liberal arts, trying oysters, and making friends with people who like books that we can truly look back and understand the complexities of the teenage mind. It is not profound each time somebody points out that the popular football captain dude does not have the happiest future, and that high school was the best time of his life, because have you asked him whether high school was the best time of his life? A million dollars to the person who shows me a former prom king saying, “High school was the best time of my life! It’s because I’ve never had ambition and also I don’t possess even a fraction of the introspective powers afforded to the nerds I mocked who now have blogs or collections of essays.”
Stay Cool is about Henry McCarthy (Mark Polish), a writer in his late 30s still haunted by the insecurities and heartbreaks of high school. (Twenty years seems the right amount of time to hold on to that stuff.) He’s written a semi-successful book about his high school experience called How Lionel Got Me Laid, and his school has asked him to give the commencement speech. He says yes, returning to his small hometown 20 years later to speak to the graduating class, but also to tie up loose ends, some very loose ends. Like, how long is that string?
It’s one thing to revisit your past as a fully formed and accomplished adult, but Henry is a fucking dud. He is sad, and he is boring, and he doesn’t seem to really appreciate or enjoy the company of those who put up with and encourage him. He’s also a terrible writer. A fake audio book of his fake novel serves as narration for much of the movie, his high school experience paralleling his return at age 37. The book is terrible. Henry says things like, “I felt like a stranger in a strange land at home” and, “Girls were a mystery to me.” What a way with words this guy has, that way he creates such vivid word-pictures. He reconnects with his two other high school weirdo friends, Brian (Sean Astin) and Wino (Josh Holloway). Brian is this odd gay caricature; he wears capri pants and Crocs, calls himself Big Girl (because Sean Astin is heavy), and says things like, “I’m bringing sexy back.” Sometimes he has a Southern accent. The main thing about Wino is that he has a man-bun and looks surprised a lot. He supports his old friend by saying things like, “Did you at least get a souvenir? Panties?” I don’t think 37-year-old dudes steal panties, or say the word panties.
Henry is still pining for Scarlet (Winona Ryder), 20 years later. (I am going to keep repeating how it’s 20 years later, because that’s nonsense. What is this, American Reunion 4?) He tutored her in chemistry and invited her to prom with a note that she ignored. Scarlet is inexplicably also at her parents’ house in their hometown, and Henry calls her up from his childhood bedroom. Correctly, she does not remember him. But they agree to meet up for a drink anyhow. What a mistake she is making.
What Scarlet doesn’t realize is that Henry’s entire book is about her. After a boring, uncomfortable date (he says “You’re pretty” within the first 11 seconds of sitting down), she says she wants to read his book. He says, “Bookstores have it. They’ll have the most recent copy.” What? The most recent copy? What are you talking about? “My novel was published a few months ago, but make sure you buy the most recent copy. There are still a lot of the old copies out there, and as you know novels change all the time, because this is Harry Potter and oil portraits talk to you.” When Scarlet asks for help finding the book at the bookstore, she’s embarrassed to say the scandalous title How Lionel Got Me Laid aloud. “You’re buying a book about a fictional character that got laid? You must be a mega-big slut.”
Meanwhile, Henry heads back to his high school and starts working on his speech. Chevy Chase plays the principal, and his primary joke is that he has a zit on his nose. Frances Conroy plays Mrs. Leuchtenberger, the English teacher assigned to approving Henry’s speech. Inexplicably, Mark sits in on her English class for what seems like weeks. When is that a thing? “Even though I’m 40 years old, I figured that since I’m giving a high school graduation speech it made sense to return home and attend high school for like two months. Really want to mix it up.” It’s in Mrs. Leuchtenberger’s class that he meets Hilary Duff, a high school student who wants to have sex with him. He doesn’t really do much to dissuade this, and it’s gross. Even grosser is that her name is Shasta, presumably as in McNasty. Henry’s return to high school is peppered with profound observations like “I just walked through a thousand memories.” I just filled a thousand buckets with barf. All the while this 37-year-old man is wearing a tiny denim jacket with a Minor Threat patch safety-pinned on the back. There is nothing more punk rock than a depressed twee memoirist.
Henry continues his courtship of Scarlet. They haven’t even kissed yet, but on their second date she is quiet for ten seconds, and he says, “You’re being really quiet. Are you not happy?” What a delight this fucking guy is. At the end of one date, she’s a little tipsy, and he pulls up at the end of the night in front of his own house. He thanks her and she scoots over to the driver’s seat. “You sure you’re okay to drive?” he says. Wow, you carless sack of wet trash juice. You get her drunk, then drive yourself home in her car and let her go the rest of the way? How about driving her home then taking a cab, or walking, or diving under the wheels of a moving bus, ideally? They finally make out after she admits she did indeed get his invite to prom, but she ignored it. They are both dreamboats.
Scarlet and Henry’s blossoming love hits a snag when her sorta-ex starts threatening Henry. The ex, Scarlet’s prom date, drives a monster truck and travels with a pack of dudes in the cab of his truck. It seems normal. Henry backs off and decides to hang out more with Shasta, who is still a child. While at a pep rally (why is he at a high school pep rally?), he sees her crying after a fight with her boyfriend, so he goes to comfort her. He refuses a hug on the grounds that it’d be a bad idea, all the while touching her back and hair and arm in the middle of a high school. Maybe you should stop that! She asks him to prom, and at first he says no, and then he asks, “What color’s your dress?” Cool, bro. Fuck that child. People who have sex with a child named Shasta should go to a special kind of prison.
Henry picks up Shasta for her high school prom in a tux, and her parents don’t seem to care. A school reporter on the red carpet of the prom (who knows) asks Shasta, “What’s it like going out with a pedophile?” That’s a great question. I hope that reporter wins a Kidz Pulitzer. At a prom after-party (where he should really not have gone), Henry finally puts a stop to Shasta’s advances. He says, “Messing around with an 18-year old won’t even come close to fixing the heartbreak I experienced 20 years ago.” Shasta’s face is all “ugh” and this is definitely the first time I’ve ever agreed with Hillary Duff and her teeth.
After Clark beats the shit out of him for no real reason (he tells Henry to stay away from Scarlet right before kissing some other girl?), Henry turns in his finished speech to Leuchtenberger, who turns it down. He scoffs that kids these days can’t “handle truth.” Shut up. He says he won’t have time to write a new speech, and she says, “You already have,” and points to his book. Perfect. Read your whole book as a graduation speech. I’m sure the kids would really appreciate all 6 hours.
Henry gets up at graduation and reads a passage from his terrible book, one that’s vaguely about the memories you take away from high school. It’s miserable. “My memories have affected the way I speak, the way I talk.” Have they? Both the way you speak and the way you talk? How about the way you communicate, and the way you project words out of your mouth? Let me know. He gets a standing ovation. Kids asks him to sign their diplomas, which is definitely not a thing. “Can you please ruin this thing my parents want to frame?”
He taps on Scarlet’s window. She’s asleep, and he lets himself into her second floor bedroom. She should call the cops. His audio book is playing on her bedside table stereo, which is unbelievable. She's already read the book, so now she’s just digesting it via the spoken word? They have sex while his audio book plays in the background, which is appropriately narcissistic for Henry. The next morning, as Henry kisses her goodbye, he says, “I love you.” That’s a bit much. Settle down. She yells back, “Henry…stay cool!” Right, like in a yearbook. In voiceover, Henry says, “Well, now I’m not afraid of love.” It only took this nightmare 37 years to get over it.
When You Should Watch This: Every year on the eve of your high school graduation anniversary, while you use a steak knife to add names to the Enemies List you keep carved in the wall next to your bed.