’90s Teen Movies That Are Basically Unwatchable Now

Ah, the 1990s. Baggy pants, flannel, floppy hair — and a memorable assortment of teen flicks that ruled the hearts and souls of fans everywhere as they popped into their local mall cineplexes. But for every “Clueless” and “10 Things I Hate About You,” there’s a “House Arrest” or “Calendar Girl.” For all of the many iconic moments the movie world gave us during that glamorous, supermodel-filled decade, there have been films which have aged less than perfectly. 

With a good three decades gone by, they’ve ended up becoming a guilty pleasure or something that quietly appalls us, while secretly tickling at our nostalgic memories. And yet they’re just so … completely unwatchable, in so many ways, whether they’re filled with offensive stereotyping, stories that are too ridiculous to be believed, and ancient morals that don’t work decades later. It’s all disgraceful and disappointing, making low points in nearly every single filmography on display here for the actors just trying to make a living.

The films listed here are wide-ranging. They could be a skateboarding epic, or perhaps a fantastic story of witchcraft — or even an attempt at a cheerful coming-of-age comedy that goes too far afield until its characters’ actions don’t reflect human emotions anymore. These flicks may have once been cool, but now they’re embarassing, cringeworthy, and even unwatchable. For those who grew up in the decade, they might have become movies worth avoiding. Tastes change, time transforms, we all age and change. The end result is a film that you may have loved once, but is tough to get through now. Here’s a long list of teen-centered films that have been made absolutely terrible with time.

The ’90s loved wicked cool, extreme films that featured their lead characters hopping about on skateboards, rollerblades, or dirtbikes. Among the decade’s cheesiest is “Airborne,” a new-kid-wins-over-the-cool-kids movie that showcases plenty of high-flipping action — but it has an ending directly ripped off from another teen epic, “Rad,” right down to having its hero and his rival mutually give up their war and cross the finish line together. It doesn’t help that this pack of “cool kids” are actually bullies and the film’s “do anything to be as cool as the bad boys” message doesn’t wash in light of how bad their behavior is. It’s likely remembered as one of a young Jack Black’s earliest roles, and because it provides a very early part for Seth Green. But in the end, it’s definitely less fun than comparable films like “The Wizard” and “Gleaming the Cube.”

Mitchell Goosen (Shane McDermott) is a cool California teen doomed to move to Ohio while his parents go on a research trip to Australia, and his only friend is his antisocial cousin, Wiley (future “Robot Chicken” maven Seth Green). Mitchell does have one thing going for him, though — he can rollerblade like a madman. Unfortunately, that makes him a target for a group of ice hockey players (of which Jack Black is the leader, bringing a malevolent edge to a typical teen bully role). Ultimately, they settle their differences the only way ’90s kids apparently know how — through a wild rollerblading contest. Much like “Thrashin’,” this movie is cheesily, embarrassingly “cool” in ways that feel cringeworthy — as though they reflect ’90s youth culture through the lens of a middle-aged studio executive who has spoken to a teenager once or twice. (This is, in fact, probably pretty close to the truth.) All of the acid-washed denim, hair gel, and kick flips lead to camp plot choices, and ultimately, disappointment. The ’90s offered teens so many other sports films, so wasting time on this one, even for the joy of basking in all of that silliness, feels like a waste of time.

The film world had a difficult time turning “Beverly Hills: 90210” king Jason Priestley’s good looks and teen heartthrob appeal into bankable movie success. One of the vehicles the actor ended up in was “Calendar Girl,” which is basically the Stephen King’s “Stand By Me” meets forgotten melodrama “Windy City.” Set in the 1960s, Priestley plays Roy Darpinian, who is obsessed with Marilyn Monroe, as are his buddies, ladies man Ned (Gabriel Olds) — often referred to by his last name, Bleuer – and the soon-to-be-married Scott (Jerry O’Connell). 

It’s the end of the trio’s innocence in many ways: As they stay in Los Angeles with Roy’s uncle, they prepare to officially say goodbye to their childhoods. In addition to hashing out personal conflicts — Roy’s desire to join the military, Ned’s pursuit of real love, Scott’s dithering about the married state –  they can’t resist trying to get a glimpse of Monroe, whom they have been obsessed with since they were kids. This creepily escalates into hapless full-blown stalking, as they try to woo her, never wondering how their idol feels about this. In fact, their misguided attempts to win her over show not only a flawed understanding of what women want, but also a lack of interest in even trying to consider how their actions might impact the object of their admiration. After all, they put a cow on her lawn in order to charm the woman, one example of the bizarre fidelity on display here. But will Miss Monroe deign to give them her attention and pity?

Aging poorly, this one suffers from a last-minute plot twist that sees the boys finally win Marilyn’s attention, with one of them going on a date with her … only to hear that later that night she died. Such a featherweight story can’t stand up to such an appalling tonal shift, or such dark subject matter, leading “Calendar Girl” to sink when it ought to swim.

“House Arrest” is “The Parent Trap” taken to the nth degree — in a bad way. Featuring a group of kids locking their parents into a basement and forcing them to work out their marital discord as they stand on the cusp of divorce and refuse to reconcile, it’s a charmless squirmathon — falling over the borderline into absurdity. 

The movie focuses on the Beindorf family — kids Grover (Kyle Howard) and Stacy (Amy Sakasitz), mom Janet (Jamie Lee Curtis) and dad Ned (Kevin Pollak). Grover is focused on keeping the family from splitting up, which leads to Janet and Ned being trapped together to work their differences out. Soon enough, other kids in the neighborhood learn about the Beindorfs’ ruse and send their own parents over to deal with their issues, allowing them to run wild while the adults beg for help. There’s the frequently-married Vic Finley (Wallace Shawn), dad of Grover’s best friend, and his latest squeeze; the sexpot mom (Jennifer Tilly) of Grover’s latest crush Brooke (Jennifer Love Hewitt); and Donald (Christopher McDonald) and Gwenna (Sheila McCarthy), who spawned town bully TJ (Russel Harper). With seven adults in the basement, can Grover win the attention of Brooke Figler, get his family back together, and avoid being grounded? (Shockingly, the answer at the end of “House Arrest” is yes — he can do all of those things.)

Rotten Tomatoes was not incorrect when they called the film “borderline irresponsible” in their description. Convincing younger teens and older kids to lock their parents up and throw the key away is a dicey proposition at best in most movies, and it definitely won’t convince any couple bent on separating to stay together. This one doesn’t inspire confidence with its wacky smugness. Grover is no Ferris Bueller, and this movie is no day off.

Some movies are retroactively cringey, because what starts out as (arguably) cool and contemporary — like a white woman going into the hood to prove that she’s down with the youth by rapping and singing with them — ends up reading like a white savior trope several decades later. It’s a storyline that’s apt to provide unintentional laughter. Michelle Pfeiffer tries her best, but she doesn’t manage to pull out anything worth remembering from the trite script. There’s a reason why this movie was mainly recalled by movie fans due to its soundtrack, headlined by Coolio’s “Gangsta’s Paradise.”

Pfeiffer plays LouAnne Johnson, a real-life teacher who used her love of poetry and Navy SEAL experience to win the appreciation of her students. For her fictionalized counterpart, that results in demonstrating karate chops and the spouting of Bob Dylan lyrics, which then reflect back to English poetry and the lesson at hand. LouAnne becomes attached to some of her pupils to their betterment and, in some cases, eventual detriment. A number of the kids turn out to be hard nuts to crack, difficult to manage due to their backgrounds or their entanglements with gangs. 

But even though some blood is spilt, they all come together to the tune of hip hop and rap, complete with a performance from her pupils in tribute to her. And yes, this is just as goofy as you imagine. There are some high points, but the “aww shucks, teach” mentality was scathingly parodied by “High School High” for a reason. “Dangerous Minds” exists to remind us that sometimes the best soundtracks come from the goofiest places.

“Teaching Mrs. Tingle” is director Kevin Williams at his most paint-by-numbers — it has his typical propensity for snark, but none of his shining wit or brilliance. It lacks the popcorn thrills we’ve come to expect from his work, and it does something fatal within its genre: It takes itself way too seriously.

It pits a group of four teens against their nasty English teacher who would like nothing more than to try to throw them all into summer school. Leigh Ann Watson’s (Katie Holmes) determination to hold on to her high grade point average, Jo Lynn Jordan’s (Marisa Coughlan) loyalty to Leigh Ann, and Luke Churner’s (Barry Watson) love of causing chaos all collide and bond the three of them together. The kids end up holding Mrs. Eve Tingle (Helen Mirren) hostage after she threatens to expel them for trying to cheat on their final exam. They respond by accidentally knocking her unconscious during a confrontation and tying her to the bed, which results in a psychological cat and mouse game between Tingle and Leigh Ann. But that requires keeping Luke and Jo Lynn under control, and that might require more effort than she can expend.

All of this should be a darkly comic, campy horror-drama, but the talented cast is wasted on a plot that’s anything but fresh and a film that just can’t rise to the occasion, in spite of a gallows-gloomy performance by Mirren. Too bad, because the whole affair could have been sublime.

The reason why “Ace Ventura: Pet Detective” hasn’t aged well is pretty obvious: The ugly transphobia too common to that era of filmmaking which permeates the fabric of the plot at several important turning points. The titular detective (Jim Carrey) is supposed to be a likable dude, sprinkling the world with potty humor and gentle malice as he risks life and limb to protect animal kind. Instead, comedy fans are just as likely to remember this film for much darker reasons, like Ace Ventura throwing up after kissing a trans woman, just as much as for him pirouetting about in a tutu or shouting “Alrighty then!” 

It’s truly unfortunate, because for every good moment, there’s a scene where Sean Young is called upon to debase herself in increasingly uncomfortable ways. The movie’s treatment of Lois Einhorn really is appalling, even though she’s a total murderer and is trying to kill Ace. We’re supposed to hate her, but the movie hates her just as much for being a trans woman as it does for all of her terrible deeds — if not more. Is her real crime the fact that she’s a murderer, or that she plays into the offensive trope of trans women as “tricking” straight men into being attracted to them?

Teens, of course, flocked to the theatres to watch Ace rescue Snowflake the Bottle Nosed Dolphin from a terrible fate. The movie spawned a sequel and a much more kid-oriented animated series, and may even be rebooted in some format in the future. But many of those youngsters probably wince when they look back on the movie now as grown-ups, and memorable scenes mix in their minds with ones that are impossible to defend.

Once upon a time, the “American Pie” franchise ruled the roost. It spawned three sequels and an endless number of direct-to-DVD releases set within the “American Pie” universe — which generally only shared Eugene Levy’s Noah Levenstein. But when push comes to shove, is it as beloved as other raunchy ’90’s teen comedies like “Can’t Hardly Wait”? Or do some moments – Jim (Jason Biggs) getting intimate with that pie, Michelle’s (Alyson Hannigan) immortal line about band camp, Stiffler’s perpetually horny mother Jeanine (Jennifer Coolidge) — stand out, while the rest of the film is an unmemorable blob? 

Several of its central plot threads certainly haven’t aged particularly well. “American Pie” still contains that scene where Jim agrees to allow his entire school to watch Nadia (Shannon Elizabeth) strip down in his room, then unwittingly do other things for the leering eyes of her classmates. In an age of cyberstalking and spyware, it’s more than icky — it can be plain unnerving. Even though it’s ultimately a disappointing and humiliating event for Jim, it’s hard to feel pity for him. After all, as we learn at so many points throughout the film, he’s often the architect of his own misfortune, and definitely not the person in this scenario that we should be empathizing with.

The film is a classic tale of boys seeking to lose their virginity on or before prom night, and all of the ridiculous lengths they go to in order to do it. For some of them, this will be a process filled with both romance and romantic anxiety. For others — see Jim — it will be a situation rife with hard knocks that mount and mount until it eventually results in triumph. Your mileage may vary when it comes to the staying power of this one — but it’s hard to deny that parts of it make the film highly unwatchable.

“Chasing Amy” can be a complex film to analyze, but it’s hard to ignore one simple fact about it: Years later, no matter how unique the movie is, rewatching it now feels like playing witness to a conversion narrative. Alyssa Jones (Joey Lauren Adams) is an out-and-proud lesbian who has dated other women before and will date other women again, yet falls in love with and has a fantastic sexual relationship with comic book writer Holden McNeil (Ben Affleck). 

But it’s a connection his ego cannot hack, as the fearlessly adventurous Alyssa has had sexual encounters with multiple individuals over her lifetime, making him feel like a rookie. The narrative, to its credit, knows Holden is in the wrong with both her and Banky Edwards (Jason Lee). Banky’s jealousy of Alyssa leads Holden to propose a threesome that none of the other parties want, but Holden needs to protect his own ego. While it’s on the border between arthouse fare and something for older teens to indulge in, its treatment of queer identity is enough to make you wince.

Alyssa and Holden fall in love, but Holden can’t let go of his jealousy over Alyssa’s broad level of sexual experience. Alyssa grapples on screen with her lesbian friends being disgusted by the fact that she’s with a man. The efforts Kevin Smith makes in “Chasing Amy” to explore bisexuality in a female character are slightly awkward and hamfisted — especially considering that the whole thing is told through the lens of a straight male character. It’s difficult to go back to, either way – a ’90s movie that didn’t age well, unfortunately.