Summary

• Iconic teen romances from the 90s and 00s still hold up today, offering unique and enduring coming-of-age stories.
• Female friendships take center stage in John Tucker Must Die, emphasizing the growth and bond between the characters.
• Bend It Like Beckham stands out with a focus on pursuing dreams over romance, offering a feel-good sports movie that inspires.

Rom-Coms have long been a staple of cinema, but the 90s and 2000s were a phenomenal time for the sub-genre, with some truly iconic characters hitting the big screen. While not every teen movie from this time period aged well, many of them remain watch-worthy for more than just nostalgia. Whether it is the beautifully executed tropes of friends-to-lovers, enemies-to-lovers, miscommunications, nerds and jocks falling in love, or just some classic teen coming-of-age stories, these remain absolute classics. And with hit movies like Anyone But You carrying on the tradition, there is a lot of debt still paid to teen rom-coms of the 90s and 00s.

Teen romance movies can be comedic high school adventures or dramas that tug at the heartstrings, but they always seem to play out like a modern fairy tale. It's not every day that a teenage outsider learns they're actually royalty or becomes embedded with the most popular kids in school, but teen rom-coms find a way to make the audience believe it. The 1990s and 2000s are two decades notorious for producing some of the most iconic teen romance movies. Many became instant classics and still hold up today.

25 John Tucker Must Die (2006)

Four Girls Team Up To Bring Down Their Ex

Teen romance movies that involve revenge plots usually employ the fake dating trope to make another character (or more than one) jealous. That’s not the case with John Tucker Must Die. Instead, a group of teenage girls team up to break the heart of a teenage boy who dated them all at the same time without them knowing. When they discover his deception, they decide to get back at him with the help of the new girl in school who will serve as his latest girlfriend.

There are not too many rom-coms of the era that focus on female friendship which is part of the reasons John Tucker Must Die stands out. While the girls initially see each other as enemies, watching their bond gradually grow is entertaining and touching. While the ending is predictable, there is enough fun chemistry among the actors and a fun bit of dark humor to make it a solid coming-of-age movie aimed at millennials.

John Tucker Must Die is available on Primevideo

24 Angus (1995)

A Bullied Kid Gets A Chance To Impress His Crush

• Release Date: September 15, 1995 (USA)
• Director: Patrick Read Johnson
• Cast: George C. Scott, Chris Owen, Ariana Richards, Anna Thomson, Charlie Talbert, Kathy Bates
• Duration: 1h 30m

Bullies are a common theme in teen movies from this era and the titular character in Angus must contend with his share of cruel classmates. A freshman in high school, Angus (Charlie Talbert) has been bullied all his life. However, when his friend rigs the school votes for Class President so Angus wins, he has the opportunity to dance with his crush and must learn how before the big dance.

The '90s teen romance movie features a lot of the teen movie tropes that are prevalent today, but it’s still a sweet story that captures the adolescent experience of being an outsider. Angus makes for an endearing hero worth cheering for. It also features the first movie role for James Van der Beek who went from playing the bully in this movie to being a teen romance idol himself.

23 Bend It Like Beckham (2002)

Two Young Girls Go For Their Dreams Of Playing Soccer

• Release Date: April 11, 2002
• Director: Gurinder Chadha
• Cast: Parminder Nagra, Keira Knightley, Jonathan Rhys Meyers, Anupam Kher, Archie Panjabi, Shaznay Lewis, Frank Harper, Juliet Stevenson
• Duration: 1h 52m

Before Keira Knightley became a star in the Pirates of the Caribbean franchise and before Parminder Nagra became a TV mainstay in ER and DI Ray, they were teenagers who just wanted to play their favorite sport in Bend It Like Beckham. The two play young women whose families didn’t want them to play football, but they found ways to be on the same team and pursue their dreams of playing professionally while falling for their coach, played by Jonathan Rhys Meyers.

Along with being a rare and excellent soccer movie, Bend It Like Beckham sets itself apart from other teen romances of the era. Instead of the romance being the main focus, this is really a story about two young women pursuing a goal that everyone else is telling them is not realistic. It makes for a feel-good sports movie about determined young girls that can inspire many others.

22 Edge Of Seventeen (1998)

A Young Boy Struggles With His Sexuality In The 1980s

• Release Date: June 11, 1998
• Director: David Moreton
• Cast: Chris Stafford,Tina Holmes, Andersen Gabrych, Stephanie McVay, Lea DeLaria
• Duration: 1h 43m

Careful not to confuse this dramedy with the 2016 Hailee Steinfeld movie The Edge of Seventeen. Both movies feature teenagers coming of age as they pursue romantic relationships, but that is mostly where their similarities end. Edge of Seventeen is set in the 1980s and follows Eric Hunter (Chris Stafford) as he slowly comes to grips with his own sexuality.

Though he gradually comes to accept that he is gay after discovering a local club and working for a lesbian who encourages him to be true to himself, Eric has a harder time admitting the truth to his best friend (who has been harboring feelings for him and thinks he’s been playing with her feelings) and his mother. The 90s proved there was still a long way to go with gay representation on screen, but The Edge of Seventeen is a touching and thoughtful gay coming-of-age story that still resonates.

21 Step Up (2006)

A Boy And Girl From Different Backgrounds Form A Bond As Dancing Partners

Dance movies became very popular in the early 2000s, and part of that was a result of the popularity of Step Up. Jenna Dewan and Channing Tatum star as teens from two very different backgrounds who share a love for dance. While she’s a modern dance student at a prestigious academy, he’s working as a janitor to fulfill community service hours after getting into trouble.

The two have different styles that they have to blend for a showcase that helps to determine both of their dancing futures and of course, they fall in love along the way. The soundtrack is great and the Step Up dance routines are beautiful to watch. Step Up spawned its own franchise, which is rare in the world of teen romance movies. It has four US sequels, a spinoff in China, a live show in India, and a streaming series on YouTube.

20 Clueless (1995)

A Rich Teen Plays Matchmaker At Her High School

Clueless

is a loose adaptation of the Jane Austen classic Emma and the classic story sees a popular, shallow, yet kindhearted protagonist, Cher (Alicia Silverstone), who means well but finds herself in a little trouble when she meddles in the love lives of her friends. However, as she attempts to find the perfect match for everyone else, Cher begins to think about her own romantic future.

Silverstone charmed audiences as Cher, being both sweet and hilarious. Brittany Murphy also became iconic as Tai with her perfect line delivery. While some of the fashion might be dated now and some of the slang might not be used today, the movie is a great snapshot of 90s cinema for teens. Silverstone and Paul Rudd's chemistry in the film is perfection among '90s movies that include teenage romance.

19 Get Over It (2001)

A Young Man Attempts To Win Back His Girlfriend

• Release Date: March 9, 2001
• Director: Tommy O'Haver
• Cast: Kirsten Dunst, Ben Foster, Melissa Sagemiller, Sisqó, Shane West, Colin Hanks, Swoosie Kurtz, Ed Begley Jr., Martin Short
• Duration: 1h 27m

Kirsten Dunst, like Reese Witherspoon and Mandy Moore, found a niche in late-90s and early-2000s teen romance movies. She appeared in many of them, and though Get Over It made a smaller splash than other teen movies in the same era, it's truly unique among the teen romances of the time. In the film, Berke (Ben Foster) is desperately trying to get his ex-girlfriend back by joining his high school's production of A Midsummer's Night Dream alongside her and her new boyfriend. As romantic comedy rules dictate, however, he ends up falling for someone else in the process.

With musical numbers and nearly all the teen rom-com tropes in one place, the movie is a fun ride. Ben Foster makes for a fun and unexpected rom-com lead with a nervous comedic energy that fits the role very well while Dunst is as charming as always. It is a reminder that sometimes teen romances of this era could work based on the likable casting alone.

18 Drive Me Crazy (1999)

A Girl And Boy Use Each Other To Make Their Exes Jealous

• Release Date: October 1, 1999
• Director: John Schultz
• Cast: Melissa Joan Hart, Adrian Grenier, Ali Larter, Gabriel Carpenter, Mark Webber, Lee Frederick Holmes
• Duration: 1h 31m

Reminiscent of the '80s rom-com Can't Buy Me Love, Drive Me Crazy features a popular girl (Melissa Joan Hart) and an outsider boy (Adrian Grenier) who strike up a deal to make their exes jealous. A makeover and a few misunderstandings later, they get their happy ending, just not in the way they expect. The '90s teen romance movie made great use of teen comedy tropes.

The movie came at the height of Melissa Joan Hart's popularity as she'd already ridden the wave of Nickelodeon's Clarissa Explains It All as a kid and Sabrina The Teenage Witch as a teen. The title also got a tie-in music video courtesy of Britney Spears, making it even more memorable for pop music fans. The movie has stayed with fans for being willing to be a bit different and quirkier than the average rom-com of the time.

17 Save The Last Dance (2001)

A Ballet Dancer Bonds With A Hip-Hop Dancer

If there's one glaring fault in late-90s and early-2000s teen romance movies, it's that the leads were very rarely people of color, or portrayed in interracial relationships. Most often, the actors of color in a teen rom-com were the best friends or the sidekicks. That wasn't so for Save The Last Dance, though the movie is more dramatic than most upbeat 2000s teen romance movies.

Another dance-centric movie, the teen romance follows Sara (Julia Stiles), who's trained in ballet, and Derek (Sean Patrick Thomas), who teaches her to loosen up with a little hip-hop. The duo has enough chemistry to carry the film themselves, but the movie is stacked with even more talent in the form of Kerry Washington and Bianca Lawson in supporting roles. The movie has a lasting legacy as Julia Stiles recently appeared on Saturday Night Live to spoof a scene from the movie.

16 Bring It On (2000)

The Head Of A Cheer Squad Competes In The Championship

• Release Date: January 5, 2001
• Director: Peyton Reed
• Cast: Kirsten Dunst, Eliza Dushku, Jesse Bradford, Gabrielle Union
• Duration: 1h 38m

Bring It On can be remembered as a sports comedy as much as a 2000s teen romance movie, but the main character of Torrance (Kirsten Dunst) does have a romantic storyline throughout the movie. She breaks up with her cheating college boyfriend and falls for her new friend's brother, all while trying to reform her cheer squad which has unknowingly been using stolen cheers.

What's really great about Bring It On is that, though Torrance gets her happy romantic ending, the movie doesn't stick to the tropes the audience knows. Torrance's team doesn't win the big championship as there is a more deserving team in the Clovers. The cheerleader culture also makes for a fun and unique world to explore. The movie also spawned a whole slew of direct-to-video sequels making cheerleading practically its own genre of teen movies.

15 How To Deal (2003)

A Young Woman Is Disillusioned About Love Until She Meets An Intriguing New Love Interest

Mandy Moore was a teen romance movie icon during the 2000s. After the immense success of A Walk to Remember, she starred a year later in a lesser-known but still popular movie titled How to Deal in 2003. The movie is a blend of the stories of two Sarah Dessen novels: That Summer and Someone Like You.

The film follows Halley Martin (Moore), who no longer believes in a perfect love story. She becomes disillusioned after her parent's divorce, her mother's loneliness, her sister's engagement, and the shallow lives of her teenage peers, but things take a turn when her best friend's boyfriend suddenly dies of a heart attack while she's pregnant. In the midst of it all, Halley starts to fall for the cool and edgy Macon Forrester (Trent Ford). The movie is able to balance its comedy and dramatic aspects with more confidence than many movies in the genre, giving it a more unique vibe.

14 Keith (2008)

A Talented Student Falls For A Carefree Classmate

• Release Date: April 11, 2008
• Director: Todd Kessler
• Cast: Jesse McCartney, Elisabeth Harnois
• Duration: 1h 35m

The pop sensation Jesse McCartney was a young star of the era who was mostly known for his popular singing career but also made the transition to acting at the height of his popularity. In 2008, fans got to see the singer-songwriter in the lead role in Keith. The independent drama is a hidden gem when it comes to 2000s teen romance movies and follows Natalie (Elisabeth Harnois), who is academically perfect and has her future mapped out before becoming lab partners with Keith (McCartney) and getting whisked into a life of carefree decisions.

However, while Keith and Natalie's relationship starts to blossom, Keith is hiding a secret that could change everything. Not a straightforward romance movie, Keith likes to challenge some of the genre conventions in taking a look at how the importance of school work and life after high school can be measured against a teen romantic fling.

13 The Princess Diaries (2001)

Anne Hathaway Stars As A Team Who Finds Out She Is Royalty

The Princess Diaries is inarguably one of the most well-known teen movies created by Disney in the 2000s, and it skyrocketed Anne Hathaway to stardom. The movie brings to life the childhood dream of living a fairytale. Mia Thermopolis (Hathaway) isn't the most popular girl in school, but one day, she learns she is of royal lineage and must train to become the royal princess of Genovia. Her famous makeover catches the attention of her crush and everyone else, but with her new fame, she starts losing the people she cares for most.

The fairy tale element of the movie makes it a magical yet grounded movie. Anne Hathaway's performance in the movie is a big reason the movie works so well as she makes the audience believe in this grounded and charming young woman's transformation into graceful royalty while also maintaining her down-to-earth personality.

12 First Daughter (2004)

The Daughter Of The American President Attempts To Find Love

First Daughter is all about Samantha MacKenzie (Katie Holmes) being fed up with her sheltered life as the president's daughter. She finally gets a break when she's allowed to attend college in California but under Secret Service protection. Her protective detail causes her trouble on many occasions, but Samantha soon meets James Lansome (Marc Blucas) and develops a close bond. James is the only one who helps Samantha feel normal for a change, but James isn't just a simple resident advisor like Samantha thought, so there are some extra twists to the tale.

It is a fun setting for the teen rom-com, taking a look at the stressful life of growing up in the public eye and under extraordinary circumstances. While the movie was not a critical hit by any means, it does have some big talents involved, including Michael Keaton as the president and Oscar winner Forest Whittaker as the movie's director.

11 What A Girl Wants (2003)

A Girl Travels To England To Meet The Father She Never Knew

In the 2000s, Amanda Bynes had more than a handful of well-recognized guilty pleasure movies from Sydney White to She's the Man. In 2003, she starred as Daphne in What a Girl Wants, and the movie's storyline was a new type of princess story. Daphne grew up not knowing her father and on her sixteenth birthday makes the journey to England to find him. She learns her father is a top politician who left his carefree life behind and as Daphne tries to assimilate into her father's life, she also falls in love with a musician.

The movie got a lot of comparisons to The Princess Diaries when it was released, but both can be enjoyed on the merits of their differences as much as their similarities. Bynes is a natural comedic talent and she puts those skills to good use in this delightful mix of teen romance and fish-out-of-water comedy.

10 Angus, Thongs And Perfect Snogging (2008)

A Young Girl Attempts To Find A Boyfriend As She Enters Her High School Years

• Release Date: July 25, 2008
• Director: Gurinder Chadha
• Cast: Georgia Groome, Eleanor Tomlinson, Aaron Johnson, Alan Davies, Tommy Bastow
• Duration: 1h 41m

Angus, Thongs and Perfect Snogging has a bit of everything for fans of 2000s teen romance movies from embarrassing comedy, and a quirky teen romance, to the qualms of trying to get through adolescence. The movie also helped to put Aaron Taylor-Johnson on the map as a heartthrob before he hit it big in Hollywood. Georgia (Georgia Groome) gets a major crush on a new student (Taylor-Johnson) and does everything possible to try and woo him.

Georgia isn't the most put-together teen and often embarrasses herself, all while worrying about her parent's relationship and the not-so-great aspects of being a teen, so it's packed with relatable moments. Though not as popular as the biggest teen romances of the 90s and 00s, it is a perfect reminder that the genre still has a lot of hidden gems to be discovered.

9 Cruel Intentions (1999)

Manipulative Step Siblings Make A Bet About Seducing An Innocent Young Woman

Cruel Intentions is a cult classic teen romance movie from the '90s, but definitely not the typical '90s movie featuring teenage romance. It's for those looking for a more twisted take on the tropes of the genre. It's based on the novel Les Liaisons Dangereuses by Pierre Choderlos de Laclos and the story is much darker and more mature in its themes than most teen romance movies.

The Cruel Intentions cast is a big selling point as it follows a privileged teen named Sebastian (Ryan Phillippe), who thinks he has it all and is untouchable, especially when it comes to his various escapades. His stepsister Kathryn (Sarah Michelle Gellar) agrees to a wager on seducing Annette Hargrove (Reese Witherspoon), the virgin daughter of the new headmaster, but his feelings get complicated. It makes for a sexy and compelling teen story with thriller elements.

8 The Prince & Me (2004)

An American Med Student Strikes Up A Romance With A Danish Prince

• Release Date: April 2, 2004
• Director: Martha Coolidge
• Cast: Julia Stiles, Luke Mably, Ben Miller, James Fox, Miranda Richardson
• Duration: 1h 51m

The Prince & Me became a well-known romance movie in 2008 because it brought to life a classic fairytale story when a normal country girl finds a royal prince to fall in love with. Prince Edvard (Luke Mably) lives his life as a playboy and refuses to accept the responsibilities of his title, and he ventures to America to experience the fun college life. He makes an impression on his lab partner, Paige (Julia Stiles) and despite trying to evade emotions, they fall in love. There's one problem, she doesn't know who he really is.

The Prince & Me made great use of the fairytale royal romance long before it became the main premise for most of Hallmark's romance movies. While the novelty of this kind of story may have worn off, this one still does it better than most.

7 Romeo + Juliet (1996)

Star-Crossed Lovers Begin A Doomed Romance

The famed love story of Romeo and Juliet has been retold and adapted many times on screen. The Shakespeare play got a revamp with a modern twist as a '90s movie of teenage romance. The movie follows the same basic storyline of two teens who fall in love despite being part of rival families. In this version, however, the rival families are rival gangs in the modern world.

The film also adds more violence, drama, and even drug use. The ending is kept relatively the same with the vials of poison and fated death, but instead of a dagger, it's a gun. The classic story loses none of its power in the adaptation though, and the performances of the cast are outstanding. Leonardo DiCaprio and Claire Danes make for an electric duo while the movie's supporting cast is also impressive with the likes of Brian Dennehy, John Leguizamo, Harold Perrineau, and Pete Postlethwaite

6 A Cinderella Story (2004)

A Lonely High Schooler Begins A Secret Romance With The School's Top Athlete

Many who grew up in the 90s and 2000s have fond memories of the movie A Cinderella Story starring Hilary Duff and Chad Michael Murray. It was a teen romance staple that modernized the popular Cinderella story. Not to mention, Chad Michael Murray was established as a teen heartthrob during the time thanks to One Tree Hill. The story follows Sam (Duff), a waitress in her father's diner run by her cruel stepmother after his passing.

After developing a friendship with a pen pal named "Nomad," they decide to meet at the Halloween dance. Dressed in a white ball gown and mask, Sam discovers her "Nomad" to be the school's popular football player. Unable to reveal her identity, she flees at midnight leaving behind her cell phone and leaving her Prince to go on the hunt to uncover who she is.