5 Classic Teen Movies That Are Unwatchable Today

Not all teen movies are created equal. For every stone-cold classic teen film — think "Clueless," "10 Things I Hate About You," and "Mean Girls" — there's one that seemed really fun at first but maybe hasn't aged all that well. What do we mean by that, exactly? Nobody sets out to make a movie that doesn't "age well," but as society evolves, we sometimes sit down, take stock, and understand that there are some jokes that shouldn't be told and lines that shouldn't be crossed ... making those movies sort of unwatchable.

Of course, that sounds extremely serious when we're talking about teen movies, but it certainly applies: teen movies are typically about young people crossing boundaries and breaking taboos, and some of them just don't hold up all that well decades down the line for a variety of reasons. Does that mean nobody should ever watch them again? No, of course not! All that it means is that, going into any one of these movies, you should have some awareness that basically none of this egregious stuff would fly anymore. As far as these five teen films are concerned, they just don't hold up to scrutiny as standards change ... from inappropriate relationships to gross jokes to reprehensible stereotypes and jokes.

Where do we even begin with "American Pie?" Directed by Paul Weitz and written by Adam Herz, this 1999 teen sex comedy centers around a group of graduating high school friends — Jim Levenstein (Jason Biggs), Chris "Oz" Ostreicher (Chris Klein), Kevin Myers (Thomas Ian Nicholas), and Paul Finch (Eddie Kaye Thomas) — all of whom are desperately trying to lose their virginities before they actually matriculate and finding it difficult for various reasons. Specifically, Jim is incredibly naïve, Oz is just sort of a dumb jock, Paul is a bit too erudite for his own good, and Kevin keeps trying to consummate his relationship with his girlfriend Vicky Lathum (Tara Reid) but failing. When they all go to a party thrown by their loutish classmate Steven Stifler (Seann William Scott) and find out one of their dorkiest classmates achieved this milestone, they make a pact that they'll all get deflowered before graduation.

The basic issue with "American Pie" is that it treats all of its female characters, including Vicky, flute player with a dirty mind Michelle Flaherty (Alyson Hannigan), Jessica (Natasha Lyonne), and especially the woman simply known as Stifler's mom (Jennifer Coolidge), a cougar with no internal motivation who ends up seducing Paul (much to Stifler's dismay). Add in a series of extremely offensive jokes and the fact that all of the boys do really gross things without facing consequences, and you've got a classic teen comedy that did not age well at all, even if the movie did create a franchise. (The less said about the titular pie, the better.)

The '80s were, to put it mildly, a very different time — and in the first of two films by John Hughes on this list, two boys literally make a woman to objectify. In Hughes' 1985 teen comedy "Weird Science," we watch, uneasily, as dorks and unpopular high schoolers Gary Wallace and Wyatt Donnelly, played by Anthony Michael Hall and Ilan Mitchell-Smith, decide to take their fate into their own hands after bullies Ian and Max (Robert Downey Jr. and Robert Rusler) mock Gary and Wyatt for lusting after their beautiful cheerleader girlfriends. When Wyatt's parents go out of town, the two "create" a dream woman on the computer, and thanks to a bizarre and apparently magical power surge, she — Lisa, played by Kelly LeBrock — comes to life and becomes their companion.

Lisa gets the boys fake IDs so they can buy alcohol and impresses everyone at their high school by, well, being really hot ... but she's also prone to erratic and bizarre behavior, like when she pulls a gun on Gary's well-meaning and deeply confused parents Al and Lucy (Britt Leach and Barbara Lang). This isn't even as weird as "Weird Science" gets, and honestly, by the time you get to the missiles and the mutant biker gangs, you're basically for the movie to wrap up its story already. "Weird Science" is a fun cult classic, sure ... but it's a teen comedy that has not aged well.

This one is ... unfortuante. In many ways, "Never Been Kissed," directed by Raja Gosnell and written by Abby Kohn and Marc Silverstein, is a classic teen rom-com, even if it is about a 25-year-old woman named Josie Geller (Drew Barrymore) who works as a copy editor at the Chicago Sun-Times and dreams of becoming a reporter for the storied newspaper. When the publication's erratic editor-in-chief James Rigfort (legendary romantic comedy director Garry Marshall) decides that Josie should go undercover at South Glen South High School, she's thrilled for the opportunity, but as Josie's brother Rob (David Arquette) reminds her, there's one big problem: Josie was a disastrous loser in high school who earned herself the cruel nickname "Josie Grossie," and she has no idea how to infiltrate the cool kids' clique and see what the teens are really up to like Rigfort wants.

With Rob's help — he also enrolls as a high school student, pretending he's not Josie's brother — Josie does, after some serious stumbles, manage to win over the popular crowd. One big problem? Her growing attraction to her English teacher Sam Coulson ("Alias" star Michael Vartan), who seems to return her feelings. Between Josie and Sam's situation and Rob openly dating an actual high school girl despite that being fully illegal, "Never Been Kissed" is definitively problematic. It doesn't matter that Josie is actually an appropriate age for Sam; it matters that he was attracted to her in the first place.

There's a lot of weird stuff in Roger Kumble's 1999 film "Cruel Intentions," despite how eminently fun and rewatchable this movie might be. With a screenplay by Kumble that adapts "Les Liaisons dangereuses" — a French novel published in 1782 by Pierre Choderlos de Laclos — "Cruel Intentions" introduces two of the most twisted step-siblings in pop culture history: Sebastian Valmont and Kathryn Merteuil, played by Ryan Phillippe and Sarah Michelle Gellar. Sebastian, who can seduce any woman he wants at any time, is bored and wants a challenge, so Kathryn sets one. If Sebastian can successfully "woo" the daughter of their school's new headmaster, the virginal Annette Hargrove (Reese Witherspoon), Kathryn will finally make his dreams come true and sleep with him. If Sebastian can't seal the deal with Annette, Kathryn gets his vintage Jaguar convertible. Along the way, Kathryn also hopes to wreak havoc on the new relationship between her ex, Court Reynolds (Charlie O'Connell), and his girlfriend Cecile Caldwell (Selma Blair).

We're aware that "Cruel Intentions" is supposed to be dark and transgressive, but honestly, the movie takes things a little far ... especially when you consider that there's also a demented plotline about a potential romance between a teacher and student in this film. "Cruel Intentions" got a small-screen reboot in 2024, but frankly, it was best to leave this one in the past.

In April of 2018, Brat Pack and teen star Molly Ringwald wrote about growing up and realizing that some of John Hughes' writing was a tad problematic ... and she honed in on the 1984 coming-of-age film "Sixteen Candles," in which she plays protagonist Samantha Baker. A lot of this movie is pretty boilerplate — Samantha hopes to have a great 16th birthday only for it to be derailed at every turn — but it has plenty of aspects that haven't aged well. "Back then, I was only vaguely aware of how inappropriate much of John's writing was, given my limited experience and what was considered normal at the time," Ringwald wrote in an essay for The New Yorker. 

"I'm a little embarrassed to say that it took even longer for me to fully comprehend the scene late in 'Sixteen Candles,' when the dreamboat, Jake [Michael Schoeffling], essentially trades his drunk girlfriend, Caroline [Haviland Morris], to the Geek [Anthony Michael Hall], to satisfy the latter's sexual urges, in return for Samantha's underwear." (Ringwald then points out that neither of them remembers the encounter after and Caroline says she "thinks" she had fun because she was unconscious. Not great!)

As Ringwald correctly pointed out, some of Hughes' scripts veer towards racism, misogyny, and homophobia (noting that homophobic slurs are used in a number of his movies). "The character of Long Duk Dong [an exchange student played by Gedde Watanabe], in 'Sixteen Candles,' is a grotesque stereotype, as other writers have detailed far more eloquently than I could," she admitted. Ringwald is exactly correct, but that doesn't mean we should give up on John Hughes movies ... just that we should be aware of their issues while watching them.