"Ferris Bueller's Day Off"
If the famous yet monotonous "Bueller? Bueller?" doesn't put you in the back-to-school mood, I don't know what will! This 1986 classic of Ferris Bueller (Matthew Broderick) and his two best buds playing the ultimate day of hooky hits just the right tone: a school-day era film rife with summertime-style antics.
"Never Been Kissed"
Did this film age well? Jury's out, but what we can all agree on is that Drew Barrymore is a freakin' delight. Josie Geller has a hard-hitting journalistic assignment in front of her, but it involves going back to high school...as a 25 year old. "Never Been Kissed" has all the trimmings of a typical high school comedy (geeks vs. jocks, prom, misguided flirtations) to put you in the mood for school.
"Dead Poet's Society"
Does back-to-school season make you nostalgic? This will hit you right where you need it to. Robin Williams (RIP, friend) is an English teacher at the elite Welton Academy in picturesque Vermont. He goes about his curriculum differently than most, but soon a group of high school boys are super into poetry and self-expression. This film will tug at your heartstrings, but it's just timeless.
"Booksmart"
We wouldn't invite the kiddos to this screening (it's been called the female "Superbad," after all), but "Booksmart" was truly a breath of fresh air when it released in 2019. Amy and Molly are about to graduate high school, but realize they spent four years purposely not getting into shenanigans, and now they think they've missed out. So commences a night of said shenanigans and lots of self-realization. You know – high school stuff.
"The Breakfast Club"
Need we say more? The '80s were the era of high school films, and John Hughes was the king. Representing every stereotypical high schooler stuck in detention together, "The Breakfast Club" is obviously a bit on the nose, but it'll strike you in the heart – in a good way.
"Matilda"
A little girl with random powers who uses them to run off the evil headmistress? Yeah, "Matilda" is Roald Dahl through and through, but that doesn't make this movie any less lovely. Between Matilda's love of reading and her super sweet algebra skills as a literal – *checks notes* – 6-year-old, it's a motivational film as we head into the next school year, at the very least.
"Monsters University"
The 2013 follow-up to 2001's "Monster's Inc." was a treat for little ones and their parents alike. Before they got into the Scare™ industry, how did Mike and Sully become partners? Like most BFF origin stories, it started at college. Watch as the two navigate collegiate life as haphazardly as any 18-year-old human would.
"Diary of a Wimpy Kid"
You could have a whole movie marathon with the book-to-film adaptations of Jeff Kinney's series! The gist? Greg Heffley is 11 years old and embarking on his journey to middle school. Though he gets off to a bumpy start, he makes it his mission to become the most popular kid in school by the time the yearbook comes out. Obviously, this proves difficult.
"Gifted"
Here's one for the parents: This under-the-radar film has everything you're looking for when the house is quiet and you're feeling like settling into something good. Namely Chris Evans in a starring role. Evans is legal guardian to his niece, who, as a first-grader, is exceptionally good at math. Teachers want him to send her to a fancy school for gifted kids, but he just wants her to have a "normal" life. The heart of this film is in its relationship-building and its ability to spark conversation.
"Are You There God? It's Me, Margaret"
The highly-anticipated adaptation of Judy Blume's beloved 1970 novel premiered in April to a whopping 99 percent on Rotten Tomatoes – it's good, people. This isn't a school-ish film, per se, but it's about the sometimes-hell of growing up and how kids and parents deal. And it's just sweet, you know? Perfect for this time of year.