15 Of The Best Teen Movie Moments (That Went Way Too Far)

Whether you danced on tables at giant house parties, drove a sick convertible to school everyday, or managed to boink the hottest MILF in your friend circle; Being a teenager rocks. Well, being a teenager in our favorite teen movies rocks. Looking back on it now, it's easy to see that the most popular teen flicks (although funny) were completely crazy and unrealistic. In fact, almost all of the best teen movies have at least one scene that had us squirming in our seats and shouting obscenities at the movie screen.

If so many teen movies were so outlandish and cringe-worthy, why do we love them so much? Perhaps it's because we enjoy living vicariously through the teenagers that were seemingly just like us, but with a little more money and way better parties to go to. Or maybe it's because we want to feel better about our more mellow, drama-free lives here in the real world.

Get ready to go down memory lane as we recall 15 of the best teen movie moments that pushed the envelope just a little too far for comfort. How many teenage shenanigans can you handle before you're crawling out of your skin?

15 A Hairy Situation


American Pie is a staple in the teen movie genre. The movie franchise somehow managed to capture the perfect amount of debauchery while still having heart. The film follows Jim (Jason Biggs) and his friends as they try to lose their virginity just in time for graduation. Because obviously, college girls would be a whole other ball game. While all three of the American Pie installments are riddled with uncomfortable moments, we really lost it during the third film, American Wedding. In the film, Jim wants nothing more than to impress his kinky band geek of a girlfriend (Alyson Hannigan) on their wedding night, so he decides to completely shave his "privates".

This is already pretty disgusting. But what makes this scene horrifying is the fact that his pubic hair manages to blow out the window, in front of a fan and ultimately collects on their beautiful wedding cake. Sure, this is just another crazy stunt the American Pie franchise is known for. But for some reason, this was just too disgusting to digest and we never thought we'd pass up a free piece of cake.

14 Underage Foul Play


Never Been Kissed follows an undercover reporter in her thirties (Drew Barrymore) as she poses as a high school student to uncover the secret lives of teens. However, as reporter Josie gets more involved in her character as a teenager, she finds herself making up for the lame, geeky teenage years she had endured herself back in high school years before. That means trying to get with the popular guy in school just so she can have a legitimate date for the prom.

In addition to that particular instance of underage foul play going on in the film, Josie's English teacher (Michael Vartan) develops a crush on Josie who he believes is another high school student. Sure, he probably picked up on her mature vibes. But still, we have to admit it's pretty inappropriate.

13 Men Betting On Women


Is it just us, or is betting money to win a woman's affection a constant theme in multiple teen movies? 10 Things I Hate About You centers around a group of kids in the same high school as each of them is linked in some way to a chain of bets going on to ultimately ensure that the two of them can date. In the film, Cameron (Joseph Gordon-Levitt) pays the school's bad boy, Patrick (Heath Ledger) to pursue Kat (Julia Stiles) so that he can date her younger sister, Bianca (Larisa Oleynik). Kat and Bianca's overprotective father made a rule that no one could date Bianca until her older sister, Cat, started dating. Still following?

What's odd about 10 Things I Hate About You is how normal and easy it is for men to bet for women's affection, completely ignoring the fact that they may have a say in this as well. The men in the movie treat the women like pawns in a game, giving teenage viewers the idea that this is a totally normal way to treat women. Sure, the movie is entertaining, but it's also pretty unsettling if you really think about it.

12 Cops Driving Drunk


There's no denying it. Superbad is probably one of the funniest teen movies ever. So, of course, there are multiple outrageous scenes throughout the movie that make it so memorable. In the film, a dorky teen befriends two police officers and ends up going on an adventure with them. However, these officers aren't the kind we see in real life. Played by hilarious comedians, Seth Rogen and Bill Hader, these two cops prove to be the worst ever, by drinking and driving on the job.

Sure, this is just a funny movie and no cop in real life would ever take some "road beers" from a crime scene with them on patrol. However, it makes us wonder if irresponsible cops like that really do exist. Especially in a time where tensions are high between police officers and civilians, it's easy to become uncomfortable at the thought of it.

11 Taking Advantage Of A Drunk Girl


The 1980's may be known for the excessive amount of spandex, big hair, and shoulder pads, but the decade also brought us some of the best teen flicks. One of our favorites is John Hughes' Sixteen Candles. The movie is about a high school student named Samantha (Molly Ringwald) who tries to win the attention of her hard-to-reach crush while dodging horn-dog dweebs. While the movie primarily follows Samantha, we also watch her dorky friend, Farmer Ted (Anthony Michael Hall) shamelessly try to get with her.

Toward the end of the film, Farmer Ted finds himself hanging out at a house party and ends up spending the night with one of the very ditzy, popular girls. However, when they awake in the morning, we learn that the popular girl was completely wasted and didn't know what she was doing. In fact, she thought Farmer Ted was her boyfriend. That means that Farmer Ted still had s*x with the woman even though she was clearly drunk out of her mind. Definitely not cool.

10 Creepy Mom Intimacy


Other than humping a freshly baked apple pie, American Pie is probably most widely remembered for it's super inappropriate "MILF" plot line. The dumb popular guy known as Stifler (Seann William Scott) happens to have a mother (Jennifer Coolidge) who is hard up for some young blood. Stifler's friend (that he doesn't actually seem to like all that much) named Finch (Eddie Thomas) ends up noticing Stifler's mom at a party and can't help but pursue her.

While the plot line is super hilarious, if that little scenario played out in real life, there'd be a huge problem. Moms generally shouldn't sleep with their teenage son's friends and can get put behind bars for doing so. But watching the funny Jennifer Coolidge be wooed by the Sinatra-loving dork, Finch is comedy gold.

9 Murder By Jawbreaker


While most teen flicks from the '90s are lighthearted and easy to watch, Jawbreaker was a whole 'nother story. The film follows a group of popular teenage girls (led by Rose McGowan) as they attempt to cover up the fact that they accidentally murdered their best friend, Liz (Charlotte Ayana). Turns out, kidnapping your BFF on her birthday and shoving her in your trunk with a giant jawbreaker in her mouth to keep her from screaming isn't the best idea.

For the entire movie, we watch the group of popular girls deal with their own guilt after killing their best friend and have everyone in the school turn on them. With bright colors, vivacious costumes, and vulgar language, it's obvious that Jawbreaker is intended to push the envelope and get the audience's attention. We have to say, there haven't been too many times a light teen flick featured cold-blooded murder.

8 Daddy Goes Too Far


Not all teen movies are necessarily comedic. In fact, some can have very relevant commentaries on today's society along with rich compelling stories. American Beauty was a film that followed a family as they navigate through life ultimately hating each other. Sounds a bit like teen years, doesn't it? The reason American Beauty goes a little too far is the fact that the father, Lester (Kevin Spacey), has a very inappropriate crush on his 16-year-old daughter's friend, Angela (Mena Suvari). Every time Lester lays eyes on Angela, he can't help but fantasize about her laying naked under falling rose petals. And he ends up having this dazed, creepy look on his face whenever he does it.

Later on in the film, Lester has the opportunity to move in on an eager Angela but he then realizes it really isn't the right thing to do. While this underage lust scenario is heinously inappropriate, it doesn't take away from the brilliance of this film. But we can't help but feel our stomachs turn every time daddy takes a visit to fantasy land.

7 Blatant Racism


If John Hughes' films are known for anything, it's definitely not for being politically correct. While we recognize this, we still can't help but cringe every time we watch the family's Asian foreign exchange student, Long Duk Dong (Gedde Watanabe) make a complete fool of himself in the classic teen flick, Sixteen Candles. Whether it's his broken English, his dumbed down behavior, or the fact that the sound of a gong plays every time he says anything.

Throughout the film, Long Duk Dong continues to make a fool of himself as he proves to be s*xually inadequate and unimportant, fueling extremely damaging stereotypes that Asian American actors have faced for decades. While quotes like "No more yanky my wanky, the Donger needs food!" may be somewhat humorous, they really are highly inappropriate and blatantly racist.

6 Inappropriate Cheerleading

"Brrr! It's cold in here! There must be some Torros in the atmosphere!" This is a chant you couldn't get out of your head for days after watching teen flick favorite, Bring It On. The film (starring the likes of Kirsten Dunst and Gabrielle Union) follows two rival cheerleading teams–one from the wealthy white neighborhood of Rancho Carne and the other from the poorer neighborhood of East Compton. The rivalry sparks some controversy and they definitely played into that in the film.

While the racist undertones were definitely worth talking about, that's not why Bring It On made this list. While practicing their cheers, one of the male cheerleader jokes about how he feels under the skirts of cheerleading girls as he lifts them up. Can we say, ew?! In multiple scenes, the male cheerleader sticks up his thumb suggesting what he is doing. That definitely wouldn't fly at any high school we went to.

5 Teenagers Playing "Love Games"


Cruel Intentions is definitely one of the darker teen movies to make our list. The film featured some A-list actors like Sarah Michelle Gellar, Reese Witherspoon, and Ryan Philipe, just to name a few. The film follows a step brother, Sebastian (Phillipe), and stepsister, Kathryn (Gellar), as they try to manipulate each other into doing really morally corrupt things. The main plot of the movie is the bet that Kathryn makes with Sebastian to see if he can nail the school's goody goody virgin, Annette (Witherspoon). The two end up falling for each other and surprise, surprise, Kathryn gets super jealous and regrets making the bet in the first place.

What's most unbelievable about Cruel Intentions is the fact that these conniving, rich AF Manhattan elite are just seventeen years old. Most of the actors were well into their twenties when they filmed the movie. Not only was Cruel Intentions incredibly unrealistic, but it really showed why hyper-s*xual love games among teenagers is a recipe for disaster.

4 The Disgusting Period Leg That Became Our Worst Nightmare


It's hard to remember a movie we laughed at harder than teen flick, Superbad. However, there was one part of the movie where we stopped laughing and started trying not to vomit. If you've seen Superbad, then you definitely remember the scene where Seth (Jonah Hill) was grinding with a hot older girl only to discover that her period had leaked onto his jeans. Really gives dirty dancing a whole new meaning, doesn't it?

Seth quickly realizes that he has menstrual blood on his jeans and becomes the laughing stock of the house party. But among the laughter, he gets approached by the girl's boyfriend who has a matching blood stain on his jeans. Can someone please get this poor girl a tampon?!

3 Poisoning Your BFF And Not Feeling Bad About It


In 1988, we got one of the most beloved cult classics, Heathers. This super dark comedy followed a group of girlfriends all named Heather (well, three of them) as they plan (and succeed) to murder their best friend. It all starts with Veronica (Winona Ryder), who becomes angry with one of the Heathers because she spreads rumors about her being prude. Veronica, with the help of her new crush, J.D. (Christian Slater), work together to poison Heather and ultimately kill her.

At school, Heather's death is deemed a suicide and everyone seems to be affected. Even an overweight, unpopular girl attempts to commit suicide to win cool points with everyone at school. In the end, Veronica ends up disagreeing with her boyfriend, J.D., as he admits he wants to blow up the entire school. In the end, Veronica ends up shooting J.D. and stopping the bomb as a way to save the entire school. Wow, talk about a dark comedy.

2 Scaring Women Everywhere Out Of Taking A Shower


Having come out in 1981, Porky's is probably the oldest teen flick to make this list. The film did pretty well in theaters despite its extremely raunchy s*xual nature. One of the most inappropriate parts about the film (and boy, there are many) is the peep hole/glory hole that famously makes an appearance. A group of teenage boys decide to have a little fun and make a spy-hole looking into the girls' locker room. At one point, one of the boys sticks his tongue in the hole followed by his...well...member.

While it was somewhat amusing in the movie, thinking about secret peepholes in the locker room, hotel rooms, or even our bedrooms is a truly terrifying thought. Unfortunately, many women deal with being stalked every day and oftentimes have their lives threatened. In real life, men spying on women in private situations is anything but a joke.

1 Filthy French Toast


Never mess with the people that handle your food. We learned this sentiment to be true in the teen movie, Road Trip. While a group of friends are on the road, they stop to eat in a diner. While they're being served breakfast, Kyle (DJ Qualls) sends back his french toast because they have far too much sugar on them. The waiter (Horatio Sanz) is upset by this and sticks the french toast down his pants as he walks around and even farts a bunch. The waiter then proceeds to serve Kyle the nasty French Toast and Kyle gobbles it right up. Disgusting!

When we go out to eat, we can't help but wonder if the kitchen staff actually does nasty stuff to our food when we send things back. While this violates health code (obviously), it's safe to assume that it does happen sometimes.

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