A Ranking Of 24 Classic ’90s Teen Movies From Worst To Best

So many heartthrobs.

Hi! We (Leonora and Erin) were both teens in the ’90s, and what a magical time it was for cinematic feats of excellence in the category of teen films. Of course, the ’90s also saw a lot of really bad shit.

We’re here to rank that bad shit from the good shit. BYEEEE.

24. Encino Man (1992)

Encino Man Productions / Via jaywalkingbackwards.tumblr.com

Leo: I have to try and remember what this was about. Sorry.
Erin: This movie singlehandedly launched my Brendan Fraser crush.
Leo: Oh god.
Erin: He’s a total babe.
Leo: For me, Brendan Fraser was already a man and therefore off limits in the crush universe. Although, I say this and yet I also had a thing for Jeff Goldblum and that was only a year later.
Erin: This is a movie about an impossible thing: a caveman coming back from… the cave. So, sorry, Fraser, but you’re terrible.

23. The Faculty (1998)

Dimension Films / Via fanbros.com

Leo: The Faculty is where they’re all aliens, right?
Erin: Legit, I have no idea. I just remember Usher.
Leo: He was in every teen movie! Why?! Well, I mean. Who doesn’t love Usher.
::: watches trailer for The Faculty :::
Leo: This is probably Kevin Williamson’s worst work. I find that disappointing.
Erin: Actually, did I see this movie? Maybe I blacked out. Usher.
Leo: This is kind of like a sexy version of a Goosebumps book. And when you think about it that way, the concept might actually be brilliant. I’m undecided.

22. Drive Me Crazy (1999)

Twentieth Century Fox Film Corporation

Leo: Ugh. This is the oldest plot in history, where it’s like, They like other people, no way they could possibly fall in love?! WHATT???
Erin: I remember thinking Melissa Joan Hart couldn’t possibly be in high school during this movie. She’s basically my age now. Also, I could not imagine them having sex together.
Leo: EWWWWWWW.

21. Dick (1999)

Columbia Pictures

Leo: I can’t believe that the movie people who make the movies got away with calling a movie Dick.
Erin: I feel like I remember Kirsten Dunst being very charming in this movie.
Leo: I remember them making outfits out of American flags, which seems strangely anti-patriotic to me. They’re actually traitors.
Erin: Maybe…?
Leo: Isn’t the dad from Clueless also Nixon in this?!
Erin: Yes. The butt chin. Unforgettable.

20. She’s All That (1999)

Miramax Films / Via croutonsforcroutons.tumblr.com

Leo: There is one scene so epically bad it might actually make this movie brilliant — when Freddie Prinze Jr. goes to Laney’s performance art thing and gets on stage to do an intense session of hackey sack.
Erin: As a former awkward child, this film gave me false hope to one day be transformed into a prom queen and be swept away by some hunk.
Leo: But if your frame of awkwardness uses Rachel Leigh Cook as a marker, then you must’ve not been that awkward.
Erin: It’s Hollywood, Leo! Awkward is glasses! I had glasses! I was also very fat.
Leo: Oh.

19. I Know What You Did Last Summer (1997)

Columbia Pictures Corporation / Via amityvilleh0rror.tumblr.com

Erin: Holy shit her boobs. That’s all I remember.
Leo: This movie is mega-scary. I’m just scared of everything, though. Like I would probably equate the same scariness of The Ring to this. But Freddie Prinze Jr… I could’ve had some nonsexual cuddling with him. Like, he was definitely sexy, but I wasn’t ready for sex. He’d wait for me.
Erin: So, basically, this movie was sexual in many ways for both of us.
Leo: Affirmative.

18. Varsity Blues (1999)

Paramount / Via movieposter.com

Leo: The dumbest shit ever.
Erin: I recall a whipped cream bra, and that really fat actor who is kind of sad in the movie.
Leo: Who’s that?
Erin: He had a funny name in the movie and a cowboy hat.
::: Leo checks IMDB:::
Erin: Billy Bob! Yes!
::: Leo and Erin Google search more :::
Leo: According to his extremely sad website, he is no longer fat. Not even close.
Leo: Oh! He was in Good Burger!

If you want to fall down a “Billy Bob” (Ron Lester) rabbit hole, here’s his website.

17. Dazed and Confused (1993)

Gramercy Pictures / Via wordpress.com

Erin: I did not understand a minute of this movie, as a Catholic school lady.
Leo: Then I think it’s an aptly named film. I feel bad about not remembering it, because it’s an iconic movie.
Erin: It’s about stoners? In California? Is that right? Are we stoned right now?
Leo: I don’t smoke weed.
Erin: I studied abroad in the Netherlands. That is all I’mma say.

16. Can’t Hardly Wait (1998)

Columbia Pictures Corporation

Leo: Ethan Embry and JLH’s spaghetti strap tank, that’s it. No, I had such a crush on Ethan Embry. I had a pinup poster in my locker of him. I loved his glasses.
Erin: I used to quote this movie all the time.
Leo: What quotes are famous from this movie?!
Erin: “Yo, I gotta get laid tonight!” And “Why you messing with my flavor, damn!”
Leo: Oh, Seth Green?
Erin: Yeah.
Leo: Remember those goggles? With the neon lenses? What was the point? Because boys didn’t wear them as sunglasses. They just sat on the top of their head. It was a headband for boys.

15. Pleasantville (1998)

New Line Cinema

Erin: You love this movie.
Leo: Yeah, this movie is amazing. A couple of years before it came out, I went through this whole obsession with the ’50s. I had multiple poodle skirts and longed for a soda shop.
Erin: I loved what a dirty bitch Reese Witherspoon was.
Leo: Oh, so dirty. So much sex. This was kind of an edgy movie! There was the masturbation thing.
Erin: All those CRAZY colors.
Leo: I would totally rewatch this movie right now.

14. Never Been Kissed (1999)

Fox 2000 / Via pastemagazine.com

Leo: A classic. I don’t know if this is actually a “good” movie, but I think it means a lot to a lot of people.
Erin: She’s not Josie Grossey anymore!
Leo: I copied her haircut.
Erin: Which haircut?! ’80s?!
Leo: The present0day one, and it just…never looked like Drew Barrymore’s. It was impossible. Very disappointing.

13. Buffy the Vampire Slayer (1992)

20th Century Fox / Via premiumhollywood.com

Erin: Some badass chick, who’s also a cheerleader, and killing folks. This was a great movie.
Leo: People totally forget that this came before the TV show. I feel like they’re totally different entities.
Erin: This movie was pretty funny, if I remember. Or I’m a sociopath. But either way, she was awesome.

12. 10 Things I Hate About You (1999)

Touchstone Pictures / Via carolizzette.tumblr.com

Erin: This was not your favorite movie, but I loved it.
Leo: I appreciate a take on a Shakespearean classic.
Erin: Which was a big fad in the ’90s.
Leo: Julia Stiles rubbed me the wrong way, but this was definitely a popular rental choice for slumber parties back in my day.
Erin: Interestingly enough, I was Kat. I am Kat. Kat forever.
Leo: Me-row!

11. American Pie (1999)

Universal Pictures / Via homeroj.tumblr.com

Erin: I saw this in theaters, with my cousin, who is a man, and it was awkward.
Leo: How old was your cousin?
Erin: Same age as me, so we were 14. And, ya know, both of our bodies were going through puberty, and a lot of this movie is about puberty.
Leo: I guess I feel conflicted because if fucking a pie means you’ve got an iconic moment in film, I don’t know what that says about American culture. Actually, did anyone think about the metaphor there? Is he fucking America?
Erin: See, I just thought it was really funny. Like, that girl went to band camp and put a flute in her see you next Tuesday.
Leo: I feel like Stifler is living in his mom’s basement, and when Siri first came out, he tried to get Siri to have cybersex with him.

10. Romy and Michele’s High School Reunion (1997)

Touchstone Pictures

Leo: This is on the cusp in the teen film category, because it’s about high school, but with…older people.
Erin: Who are our age now, in the movie, I suppose. Does that make you feel old?
Leo: I guess?
Erin: Remember when she tries to go on Singled Out? And she’s too old? Because the cutoff is 25?!
Leo: That makes me feel sad, yes. But…I feel like this is a really satisfying movie, because they end up with a cute boutique, and Michele has like, a rich, awesome boyfriend.
Erin: Yeah, their store was really bright and colorful. Like Nasty Gal, pre-Nasty Gal.
Leo: Mmmm hmm.
Erin: Also, I really loved…what’s her name? The cigarette one?
Leo: Janeane Garofalo.
Erin: That’s the one. I’m old. I forget things.

9. Election (1999)

Paramount / Via okmoviequotes.com

Leo: I mean, this is just a brilliant, brilliant movie.
Erin: Tracy Flick and I have a lot in common.
Leo: I can see that. I mean not the sleeping with your teachers part, but the winning at everything part.
Erin: I’m a little obsessive. And I like baking to win people’s affections.
Leo: I like how, close to the end, Matthew Broderick sees Tracy Flick as a young Washington intern outside the White House. Hello! Foreshadowing for Legally Blonde II.
Erin: :::mouth falls open in shock::: Also, that movie taught me that eating asparagus makes your pee smell funny.
Leo: Good to know.

8. Don’t Tell Mom the Babysitter’s Dead (1991)

Cinema Plus / Via retroland.com

Leo: Everything I thought about jobs and professional life came from this movie.
Erin: She was so cool. With her sunglasses and her blonde hair, and her fancy job with the petty cash! She had it all!
Leo: The outfits at the end were absolute insanity. It was like the Jetsons went to the circus and decided to be hotel maids.
Erin: Also, the premise for this movie is insane.
Leo: Is there a dead body rotting away for weeks?
Erin: I think they bury her. Like, they have a whole funeral! Right?
Leo: ::: looks up the plot ::: Oh! They stuff her body in the trunk of a car, and drop her off at a funeral home and keep the car.
Erin: Naturally.

7. Now and Then (1995)

New Line Cinema / Via fanpop.com

Erin: This movie made me nostalgic for a time I never really knew: the ’60s. It’s just really girly and sweet.
Leo: There are a lot of really dark scenes too, but what about that scene where they stumble upon a Vietnam vet…
Erin: Brendan Fraser!
Leo: Oh my god, no! Seriously?! Well, he was creepy. He was kinda creeping on those young girls. I feel like that was a window into all the bad things those girls would do as teens.
Erin: I was totally Roberta.
Leo: Horrible name.
Erin: Agreed.

6. Scream (1996)

Dimension Films / Via tumblr.com

Erin and Leo at the same time: So scary.
Leo: Jinx!
Erin: I remember renting this movie and inviting my friends over to watch, and their parents had to give them permission to watch.
Leo: Oh man, that’s hardcore. Definitely a very scary movie, but also very important in the canon of ’90s teen cinema.
Erin: Another Kevin Williamson piece too.
Leo: ::: hums Dawson’s Creek theme song :::

5. Romeo + Juliet (1996)

Bazmark Films

Erin: Holy shit. This movie.
Leo: So emotional. Best soundtrack in the world. I still listen to it on a regular basis.
Erin: Yes. Also, Leonardo DiCaprio eye-fucks the shit out of the camera. Gave me a lotta feels.
Leo: Angel wings. That was totally a fashion thing after this movie.

4. Empire Records (1995)

Warner Bros. / Via survivingcollege.com

Leo: This movie is all about Liv Tyler and that outfit — Dr. Martens, pleated skirt, mohair belly top.
Erin: Everyone was so pretty and so ’90s.
Leo: It’s also kinda sad, looking at it now, because the record-store culture was brutally murdered by Napster. And that was a young-people thing that was just kind of gone not too long after this movie.
Erin: I remember buying tapes. And song singles. And yeah, I miss music stores.

3. The Craft (1996)

Columbia Pictures Corporation / Via alyce-in-bloom.tumblr.com

Erin; Oh my god, I wanted to be a witch so bad.
Leo: Ahhh! Yaaas. Did you also play “Light as a feather, stiff as a board” with your friends?
Erin: YES! I bought a book about how to be a Wiccan.
Leo: Oh yeah, Wicca became huge after this movie. I think everyone did that. And Sage.
Erin: I still kinda want to be a witch.
Leo: Totally.

2. Clueless (1995)

Paramount Pictures / Via celebuzz.com

Leo: I mean, Clueless is just the most beautiful intersection of 19th-century British literature and kilts.
Erin: I wanted to be Cher. I loved everything about her. And yet, I missed half of the drug references. I was only 10, to be fair.
Leo: Clueless changed my life. Turning point.
Erin: Agreed.

1. Cruel Intentions (1999)

Columbia Pictures Corporation / Via tardisbuttonsquid.tumblr.com

Erin: I used to have this entire movie memorized.
Leo: That’s impressive.
Erin: I had the VHS tape, and I would watch every day after school. No joke.
Leo: That’s kind of a lot, but I understand where you’re coming from. So sexy. Also, I grew up in Manhattan and they lived in that house on 5th Avenue, and that would be the dopest house to live in. This is Gossip Girl 1.0 for sure.
Erin: It also really, really, really gave me a false sense of what losing your virginity would be like.
Leo: Oh, right. Also, isn’t this based on Dangerous Liaisons? So it’s cultural AND sexy.
Erin: That’s what I told myself. What I still tell myself.

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