When your hormones start raging in junior high and high school, where do you turn to learn some serious romance moves? Movies, of course! The teen romance is a tried and true genre that has spanned many generations and is still going strong today. The ‘90s featured some truly great teen romances, with the year 1999 in particular really hitting it out of the park in terms of quantity — half of the movies below are from 1999!
But let’s get to what you’re here for – our list of the top 10 best ‘90s teen romance movies. Whether you want comedy, drama, or just a chance to swoon a little, these ‘90s classics totally have your back.
Love the ’80s? Check out our article: The Top 10 ’80s Teen Romance Movies to Remember – Ranked
10. Empire Records (1995)
Okay, so technically it’s a little bit of a stretch to consider Empire Records a teen romance, as it’s really more just a straight up dramedy, but there is a whole subplot about a romance between Liv Tyler’s character Corey and Johnny Whitworth’s character AJ. Honestly, AJ was so swoonworthy, it just made Corey look like an idiot that she wasn’t sure if she liked him.
9. Drive Me Crazy (1999)
If you’re looking for a typical teenage trope, look no further than Drive Me Crazy, starring Melissa Joan Hart and Adrien Grenier. The two play characters on opposite ends of the social spectrum at school who decide to pretend to date each other in order to make their exes jealous. Of course, they eventually start to fall for each other.
8. Cruel Intentions (1999)
Now here we have something a little different, and definitely darker, with Cruel Intentions. While a lot of these movies involve hijinks in the form of someone pretending to like someone for their own gain or having some kind of bet, those hijinks/bets were never to the target person’s detriment. But in this movie, hurting others was absolutely the name of the game. If you ever wanted to see Sarah Michelle Gellar take on a villainous role, this one’s for you.
7. Ever After: A Cinderella Story (1998)
Though Ever After does not take place during the modern day, it still features a teen heroine in the lead role, with Drew Barrymore taking on the role of Danielle, who is really just meant to be a version of Cinderella. Though we all know how this story goes, the movie is nonetheless very sweet and does have some more female empowerment in it than the typical Cinderella story.
6. Can't Hardly Wait (1998)
Honestly, Can’t Hardly Wait is underrated. Though we wouldn’t typically argue that ensemble movies are great, in this case we make an exception. The film follows a group of teenagers who have just graduated high school on the night of a big celebratory party. The teens fit into different high school cliche stereotypes — the jock, the nerd, the popular girl, the outcast, etc. The main story revolves around Ethan Embry’s character trying to profess his love for Jennifer Love Hewitt, but some of the most memorable moments come from everyone else.
5. Never Been Kissed (1999)
Yes, yes, the main characters in Never Been Kissed may no longer be high school age, but the movie takes place at a high school and features copious flashbacks, so it counts, okay? This movie stars Drew Barrymore at her best, playing nerdy and shy copy editor Josie Gellar who goes undercover at a high school to get her first writing gig at her newspaper. Of course, she ends up falling for her English teacher while undercover. Shocking, we know. Still, the movie is cute and sweet and always makes you feel good.
4. William Shakespeare's Romeo + Juliet
Now if what you want is to leave a movie feeling bad at the end rather than good, then Romeo + Juliet is the movie for you. Everyone knows the tragic story, but it got a modern, colorful, music-filled remake in this version directed by Baz Luhrmann and starring Leonardo DiCaprio and Claire Danes as the erstwhile Romeo and Juliet. If you wanted to get your teenager into Shakespeare, there was no better way to introduce them than through this tragedy of beautiful people dying tragically. Did we mention it’s tragic?
3. She's All That (1999)
Freddie Prinze Jr. and Rachael Leigh Cook star in She’s All That, a classic tale of a bet turning into true love. Truly, there are so many cliches in this movie, like the nerdy person being secretly hot underneath (though was it really that secret here?), the jock being secretly smart and not that much of a jock, the grade A bitch getting what’s coming to her… all of that’s here in spades. But thanks to the likable cast and some interesting quirks along the way, it works.
2. 10 Things I Hate About You (1999)
If you don’t love 10 Things I Hate About You, do you not have a soul? Seriously, this movie is awesome. Another modern take on a classic Shakespearean tale (The Taming of the Shrew), but this time without the iambic pentameter, 10 Things is another tale of pretend like leading to real love. Heath Ledger’s character is paid to take out Julia Stiles’ so that her father will allow her younger sister, played by Larisa Oleynik, to go on dates as well. Oleynik wants to date the popular doofus played by Andrew Keegan, but also has the sweet Joseph Gordon-Levitt pining after her in what is clearly a better match. Obviously, the cast in this film is awesome and the movie is still very watchable to this day.
1. Clueless (1995)
As if we could choose any other movie to be at number one! Here we have another take on a literary classic, this time Jane Austen’s Emma. Written and directed by Amy Heckerling, Clueless is about high schooler Cher, played by Alicia Silverstone. Cher envisions herself as a bit of a matchmaker at her school, working her charms on two teachers before turning to new girl Tai, making her a sort of pet project. While Cher is great at helping others, she’s not so great at seeing what she needs herself. Seriously, you can’t consider yourself a ‘90s kid or even just a ‘90s fan if you don’t love Clueless, and that’s a fact.
- Apparently, Empire Records was severely edited in post production, cutting three major characters, about forty minutes of footage, and also condensing the action from two days down to one day.
- Many different actors that would go on to be big names auditioned for the various roles in Clueless, but one of note was Sarah Michelle Gellar, who was actually offered the role of Cher, but had to turn it down due to her time commitment to All My Children.
- 10 Things I Hate About You was turned into a short-lived television series in 2009 for ABC Family (now Freeform). It was actually a really fun show and it’s too bad that it got canceled.
- In She’s All That, Kieran Culkin’s character (he plays the younger brother of lead Laney) wears hearing aids. However, these hearing aids are never addressed, and Culkin has since stated he doesn’t know why he was wearing them either.
- Natalie Portman was originally meant to play Juliet in Romeo + Juliet, but studio executives didn’t like her pairing with Leonardo DiCaprio as she was much younger — she was only 14 at the time of filming, while DiCaprio was 21.
- Apparently, Empire Records was severely edited in post production, cutting three major characters, about forty minutes of footage, and also condensing the action from two days down to one day.
- Many different actors that would go on to be big names auditioned for the various roles in Clueless, but one of note was Sarah Michelle Gellar, who was actually offered the role of Cher, but had to turn it down due to her time commitment to All My Children.
- 10 Things I Hate About You was turned into a short-lived television series in 2009 for ABC Family (now Freeform). It was actually a really fun show and it’s too bad that it got canceled.
- In She’s All That, Kieran Culkin’s character (he plays the younger brother of lead Laney) wears hearing aids. However, these hearing aids are never addressed, and Culkin has since stated he doesn’t know why he was wearing them either.
- Natalie Portman was originally meant to play Juliet in Romeo + Juliet, but studio executives didn’t like her pairing with Leonardo DiCaprio as she was much younger — she was only 14 at the time of filming, while DiCaprio was 21.
