’90s Teen Movies That Are Basically Unwatchable Now

Ah, reminiscing about the 1990s! The era was marked by baggy pants, flannel shirts, and plenty of floppy hair. Teen movies dominated our local cinemas then, with some like “Clueless” and “10 Things I Hate About You” becoming timeless classics. However, for every beloved movie, there were films such as “House Arrest” or “Calendar Girl” that didn’t age quite as gracefully. Despite the numerous iconic moments the film world gifted us during this glamorous era filled with supermodels, some movies haven’t stood the test of time as well as others.

After about three decades, these films have become a mix of amusement tinged with guilt or something that subtly shocks us, but at the same time stirs up our nostalgic feelings. However, they’re nearly impossible to watch due to offensive stereotyping, implausible stories, and outdated morals that no longer apply in today’s world. It’s all rather shameful and disheartening, with many of these films falling short in almost every aspect for actors struggling to earn a living.

These movies on the list span a variety of genres. They could be an intense skateboarding saga, a spellbinding tale of witchcraft, or even a lighthearted coming-of-age comedy that strays too far and no longer resonates with human emotions. Initially, these films might have been trendy, but now they’re awkward, painful to watch, and sometimes unbearable. For those who lived through the era, they may have become movies best avoided. Tastes evolve, time alters, we all grow and change. The outcome is a film that you once cherished, but now finds it hard to endure. Here’s a lengthy list of teen-focused films that have lost their charm over time.

Airborne

90s audiences were drawn to action-packed movies that showcased characters performing stunts on skateboards, rollerblades, or dirtbikes. One of the most cheese-tastic examples from this era is “Airborne,” a film about a newcomer winning over the popular crowd. The movie offers lots of high-flying action, but its ending is almost identical to another teen classic, “Rad.” This similarity extends to the final scene where the protagonist and his rival put aside their rivalry and cross the finish line together, just like in “Rad.” Unfortunately, this group of “cool kids” are actually bullies. The film’s message about doing anything to be cool like the bad boys doesn’t sit well with viewers given how poorly they behave. It’s noteworthy for being one of Jack Black’s early roles and for providing an early part for Seth Green. However, when compared to similar films such as “The Wizard” and “Gleaming the Cube,” it falls short in terms of entertainment value.

The character Mitchell Goosen (portrayed by Shane McDermott) is a popular California teenager who has to relocate to Ohio due to his parents’ research trip to Australia. His sole companion is his aloof cousin, Wiley (later known for creating “Robot Chicken”), and the only advantage he has is his exceptional rollerblading skills. However, this talent makes him a victim of a gang of ice hockey players, led by Jack Black who gives a sinister twist to the typical teenage bully. To resolve their conflicts, they choose an extreme rollerblading competition – reminiscent of the movie “Thrashin”. The film is overtly ’90s in its portrayal of coolness, but this feel can be awkward and cringeworthy. It seems like it attempts to depict ’90s youth culture through the perspective of a middle-aged studio executive who rarely interacts with teenagers. This is reflected in the film’s excessive use of acid-washed denim, hair gel, and tricks like kick flips, leading to questionable plot decisions, leaving viewers feeling let down. Despite offering many other sports films during the ’90s, spending time on this one feels like a waste, even for the pleasure of indulging in all that nostalgic silliness.

Calendar Girl

In the movie industry, it was challenging for Jason Priestley, known as the king of “Beverly Hills: 90210” and teen idol, to translate his handsome looks and heartthrob charm into box office hits. One of the roles he eventually took on was “Calendar Girl,” which can be seen as a blend of Stephen King’s “Stand By Me” and the nearly forgotten melodrama “Windy City.” This film, set in the 1960s, features Jason Priestley playing Roy Darpinian, a man captivated by Marilyn Monroe, much like his friends, the smooth-talking Ned (Gabriel Olds), also known as Bleuer, and the soon-to-be-married Scott (Jerry O’Connell).

As the trio – Roy, Ned, and Scott – spend time with Roy’s uncle in Los Angeles, they are essentially leaving their youth behind. They deal with internal struggles like Roy’s enlistment in the military, Ned’s search for genuine love, and Scott’s indecision about marriage. Despite this, they can’t help but be drawn to Monroe, a girl they’ve been infatuated with since childhood. Unfortunately, their fascination turns into stalking as they try to capture her affection, without considering how she might feel about it. Their clumsy attempts at winning her over reveal more than just a misunderstanding of what women desire; they also show a lack of concern for the potential harm they could cause. In one instance, they leave a cow on her lawn in an attempt to impress her – a strange display of devotion. However, it remains to be seen if Monroe will acknowledge them or pity their misguided advances.

The narrative of this work unfortunately falters as it nears its end, with the boys unexpectedly gaining Marilyn’s affection, one even going on a date with her. However, the grim twist follows that very night she passes away. Such a lightweight plot struggles to bear the sudden change in tone or the heavy theme, causing “Calendar Girl” to flounder instead of thrive as it should.

House Arrest

House Arrest” can be rephrased as “The Extreme Parent Trap,” where the situation escalates dramatically beyond the original story. Instead of two sisters switching places, in this case, children keep their parents confined to a basement, pushing them to resolve their marital issues that are on the verge of divorce and unwilling to reconcile. The atmosphere is far from charming, more like an exhausting rat race — venturing dangerously close to the realm of the absurd.

The film centers around the Beindorf family consisting of children Grover (Kyle Howard) and Stacy (Amy Sakasitz), parents Janet (Jamie Lee Curtis) and Ned (Kevin Pollak). Determined to keep the family united, Grover’s actions force Janet and Ned into resolving their differences. As word spreads among other neighborhood kids about the Beindorfs’ scheme, their parents are lured over to handle their own issues, giving the children free rein. Characters like the multiple-time married Vic Finley (Wallace Shawn), father of Grover’s friend, his current partner; the seductive mother (Jennifer Tilly) of Grover’s love interest Brooke (Jennifer Love Hewitt); and Donald (Christopher McDonald) and Gwenna (Sheila McCarthy), parents of town bully TJ (Russel Harper), also play significant roles. Faced with seven adults in the basement, can Grover manage to capture Brooke Figler’s attention, reunite his family, and escape punishment? Remarkably, by the end of “House Arrest,” Grover accomplishes all three feats.

Rotten Tomatoes wasn’t off-base when they labeled the film as “borderline reckless” in their review. Encouraging younger teens and older kids to imprison their parents isn’t a smart move in most films, and it certainly won’t persuade any couple on the verge of separation to reconcile. This movie lacks credibility with its overconfident tone. Grover is no match for Ferris Bueller, and this film isn’t a fun day off.

Dangerous Minds

In some instances, movies that were once considered hip and modern can later feel awkward or embarrassing, such as when a white actress attempts to connect with urban youth by rapping and singing with them. This narrative often appears as the white savior trope in retrospect. It’s a plot line that might unintentionally elicit laughter from viewers today. Michelle Pfeiffer gives her all, but she fails to create anything memorable from the clichéd script. The film is mainly remembered by movie enthusiasts for its popular soundtrack, particularly Coolio’s “Gangsta’s Paradise.

In this rephrased version: Pfeiffer portrays LouAnne Johnson, a true-life educator who combines her passion for poetry and military expertise from the Navy SEALs to gain the respect of her students. For her fictional representation, this leads to showing off karate moves and quoting Bob Dylan songs, which in turn connect to English literature and the lesson being taught. LouAnne develops emotional bonds with certain students, benefiting some while potentially causing harm in others. Some of the students prove challenging, as they come from troubled backgrounds or are involved with gang activities.

Despite the shedding of some blood, they all unite to the rhythm of hip hop and rap, which includes a tribute performance by her students. Yes, it’s as quirky as it sounds. While there are some touching moments, the overly casual demeanor was humorously criticized in “High School High”. “Dangerous Minds” serves as a reminder that extraordinary music can emerge from the most unlikely sources.

Teaching Mrs. Tingle

Director Kevin Williams delivers a predictable effort with ‘Teaching Mrs. Tingle,’ as it showcases his usual sarcastic style, but falls short on the cleverness and ingenuity that are his hallmarks. The film fails to deliver the entertaining suspense that we’ve grown accustomed to from him, and instead, it makes a grave mistake within its genre – it is far too self-important.

The story revolves around four teenagers, including Leigh Ann Watson (Katie Holmes), Jo Lynn Jordan (Marisa Coughlan), and Luke Churner (Barry Watson), who find themselves at odds with their stern English teacher, Mrs. Eve Tingle (Helen Mirren). Leigh Ann’s desire to maintain her high academic standing, Jo Lynn’s loyalty towards Leigh Ann, and Luke’s knack for causing trouble combine to form a strong bond between them. A series of events unfolds when Mrs. Tingle threatens to expel them for attempting to cheat on their final exam, leading the students to take her hostage. Their actions inadvertently knock Mrs. Tingle unconscious during an altercation, and they tie her to a bed. This situation triggers a psychological game of cat and mouse between Tingle and Leigh Ann. However, keeping Luke and Jo Lynn under control proves challenging, a task that might demand more energy than Leigh Ann can muster.

The movie aims for a darkly comical, over-the-top horror-drama, but unfortunately, the storyline fails to deliver on this promise. Despite a stellar cast and Mirren’s captivating performance, the film lacks originality and falls short of its potential, leaving us wishing it could have been something truly exceptional.

Ace Ventura: Pet Detective

It’s quite clear why the movie “Ace Ventura: Pet Detective” doesn’t seem as fresh today – it’s heavily tainted by the insensitive transphobia that was prevalent during its production era. Despite Jim Carrey’s character being intended to be charming, with his humor often bordering on potty and mischievous, many comedy enthusiasts recall this film more for troubling moments, such as Ace Ventura vomiting after kissing a transgender woman, rather than his antics like dancing in a tutu or saying “Alrighty then!” This movie unfortunately stands out more for the wrong reasons.

It’s regrettable that despite some positive moments, the film consistently degrades Sean Young’s character, Lois Einhorn, by requiring her to demean herself in increasingly awkward situations. The portrayal of this character is shockingly poor, especially given that she’s a murderer intent on killing Ace. Yet, it seems the movie loathes her not just for her heinous actions, but also because she’s a trans woman. In fact, it appears the film may despise her for being trans more than for her criminal acts – if such a thing can be said. Is it Lois Einhorn’s real crime that she’s a murderer or that she reinforces the harmful stereotype of trans women as deceivers who manipulate straight men into falling for them?

Adolescents rushed to cinemas to witness Ace saving Snowflake, the Bottle Nosed Dolphin, from a dire situation. This film led to a sequel and a more child-friendly animated spin-off, and there’s speculation that it could be reimagined in some way later on. However, many of those kids might cringe at the memory of the movie as they grow older, as cherished moments become blurred with ones that are hard to justify.

American Pie

Back in the day, the “American Pie” series was the talk of the town. It gave birth to multiple sequels and countless straight-to-video spin-offs within its universe, primarily revolving around Eugene Levy’s iconic character, Mr. Levenstein. However, when it comes down to it, does it hold a candle to other ’90s raunchy teen comedies like “Can’t Hardly Wait”? Or does the pie scene with Jim (Jason Biggs), Michelle’s (Alyson Hannigan) legendary band camp quote, and Stiffler’s mom Jeanine (Jennifer Coolidge) and her ever-horny persona stand out, while the rest of the series feels a bit forgettable?

The main storylines of “American Pie” may not hold up particularly well given today’s standards. For instance, a scene where Jim allows his schoolmates to watch Nadia (Shannon Elizabeth) strip down in his room is quite problematic nowadays. With the prevalence of cyberstalking and spyware, it’s beyond being just awkward – it can be downright unsettling. Despite the fact that this incident turns out to be a humiliating experience for Jim, it’s challenging to feel sympathy for him since we learn throughout the movie that he often brings misfortune upon himself and is not exactly the character we should identify with emotionally.

The movie tells an age-old story about a group of young men striving to lose their first sexual experiences before or at their prom, going to extreme and absurd lengths to achieve it. Some will experience a mix of romance and nervous anticipation throughout this journey, while others, like Jim, face a series of harsh lessons leading to eventual success. Whether you find this film enduringly compelling or occasionally uncomfortable is subjective, but it’s undeniable that certain parts might make for difficult viewing.

Chasing Amy

Analyzing ‘Chasing Amy’ can be challenging due to its complexity, but one undeniable aspect is clear: viewed years later, the movie seems to depict a transformation story. Alyssa Jones (played by Joey Lauren Adams) is openly lesbian, with a history of relationships with women, yet she falls in love and has an incredible romantic and sexual relationship with comic book writer Holden McNeil (Ben Affleck).

However, Alyssa’s bold sexual history is too much for his ego to handle, making him seem inexperienced in comparison. The story acknowledges Holden’s wrongdoing towards both Alyssa and Banky Edwards (Jason Lee). Banky’s jealousy of Alyssa drives Holden to suggest a threesome, an idea that none of them are comfortable with, but he feels compelled by his ego. The film, while bordering on art-house cinema and suitable for mature audiences, handles queer identity in a way that can be uncomfortable to watch.

In my gaming world, I find myself entangled in a tale where Alyssa and Holden kindle a deep affection. However, Holden struggles to move past his unease due to Alyssa’s extensive romantic history. Meanwhile, Alyssa confronts the disapproval of her lesbian friends for choosing a man. The portrayal of bisexuality in Kevin Smith’s “Chasing Amy” feels a bit clumsy and forced – even more so because this story is being narrated by a straight male character. Rewatching it now, the ’90s vibe is strong, but not in a way that makes for an easy revisit.

2025-03-24 23:32