30 Unforgettable Teen Romance Movies From The 90s & 2000s

Stories of young love have always captured the attention of moviegoers and the 1990s and 2000s saw a lot of teen romance movies add to the genre. 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.

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.

You are watching: 30 Unforgettable Teen Romance Movies From The 90s & 2000s

30 But I’m A Cheerleader (1999)

A Teen Finds Her Sexuality At A Conversion Therapy Camp

But I’m A Cheerleader R

But I’m a Cheerleader follows Megan, an all-American high school cheerleader, who is sent to a conversion therapy camp by her conservative parents after they suspect her of being a lesbian. The film explores her experiences at the camp as she navigates her identity and relationships.

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*Availability in US Director Jamie Babbit Release Date July 7, 2000 Cast Natasha Lyonne , Clea DuVall , Cathy Moriarty , RuPaul , Melanie Lynskey , Katharine Towne , Katrina Phillips , Joel Michaely , Douglas Spain , Kip Pardue , Eddie Cibrian , Michelle Williams , Brandt Wille , Bud Cort , Mink Stole , Katie Donahue , Danielle Reneau , Dante Basco , Kyle Thatcher , Robert Pine , Rachelle Carson , Wesley Mann , Richard Moll , Julie Delpy Runtime 85 Minutes Expand

While the 90s were starting to see a little more LGBTQ+ stories being represented in movies, it was still rare to have such relationships explored in a teen romance movie. However, But I’m a Cheerleader took a bold step in addressing these types of romances while also being a funny satire of the anti-gay community.

Natasha Lyonne stars in the movie as Megan, a popular high school cheerleader whose parents suspect that she is gay and send her to a camp that is designed to “convert” gay teens. The movie is a hilarious and elevated comedy that is poking fun at the idea that such a lifestyle can and needs to be “cured.”

It is especially funny as the camp gives Megan an opportunity to really explore her feelings with another camp member, Graham (Clea DuVall). Their defiant yet intimate romance that forms allows them both to be free in ways they never could and to discover themselves.

29 American Pie (1999)

Four Friends Try To Lose Their Virginity Before High School Ends

American Pie R

American Pie is a raucous teen comedy and the film that launched a revival of the genre. It follows a group of high school friends determined to lose their virginity before graduation and delves into the misadventures of the four boys as they navigate the complexities of relationships, peer pressure, and parental mishaps. You’ll never look at warm apple pie the same again.

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*Availability in US Director Paul Weitz , Chris Weitz Release Date July 9, 1999 Cast Jason Biggs , Chris Klein , Thomas Ian Nicholas , Alyson Hannigan , Shannon Elizabeth , Tara Reid Runtime 95 minutes

American Pie is often looked at as the beginning of the gross-out teen comedy phase. While that might be true, that doesn’t mean there is not also room for some romance amid all the dirty jokes. The movie follows four male friends who make a pact to have sex before the end of their high school senior year.

However, each of them encounters more than a few obstacles along the way. American Pie deals with several different romances over the course of the movie. Ox (Chris Klein), the popular jock, finds himself falling for studious Heather (Mena Suvari).

There have been nine
American Pie
movies to date.

Meanwhile, high school sweethearts Kevin (Thomas Ian Nicholas) and Vicky (Tara Reid) deal with the idea of their romance coming to an end as they go their separate ways after high school. While not the deepest of romances, the movie deals with teen relationships in a relatable way. While the American Pie movies continued with several sequels and spinoffs, none of them topped the humor and heart of the original.

28 Can’t Hardly Wait (1998)

An Outsider Tries To Woo A Popular Girl At A High School Party

Can’t Hardly Wait PG-13

School is finally over, and a diverse group of graduating seniors—from athletes and popular students to the academically inclined—converges at a rich classmate’s house for a celebration. At the party, artistic Preston (Ethan Embry) aims to confess his long-held feelings to Amanda (Jennifer Love Hewitt), the school’s most admired beauty. Meanwhile, geeky William (Charlie Korsmo) plots revenge against jock Mike (Peter Facinelli) for years of torment. In another twist, aspiring rapper Kenny (Seth Green) finds himself accidentally trapped in a room with the sarcastic Denise (Lauren Ambrose).

Director Deborah Kaplan , Harry Elfont Release Date June 12, 1998 Cast Ethan Embry , Charlie Korsmo , Lauren Ambrose , Peter Facinelli , Seth Green , Jennifer Love Hewitt Runtime 101 Minutes

Can’t Hardly Wait is another teen comedy that features some memorable romances alongside juvenile humor. The movie centers around various characters coming together at an epic high school party. At the center of the story is Preston (Ethan Embry), an outsider in his school who decides to attend the party with the sole intention of professing his love for the popular girl, Amanda (Jennifer Love Hewitt), who he’s long admired from afar.

Can’t Hardly Wait is inspired by the movies of John Hughes and the teen romances of the 1980s, effectively recapturing that vibe. The central story of the unpopular kid trying to get his shot at a girl who is out of his league is a well-known one used in many rom-coms of the 80s and 90s, but Can’t Hardly Wait manages to make it charming, thanks largely to its likable cast.

27 Y Tu Mamá También (2001)

Two Best Friends And An Older Woman Set Out On A Road Trip

Y Tu Mamá También Not Rated

Julio and Tenoch are two teenagers who, together with Luisa, an older woman, embark on a journey to a paradise beach. On a road trip through Mexico, the three end up getting involved and learning a lot about themselves and their relationships.

Release Date June 8, 2001 Cast Maribel Verdú , Gael García Bernal , Diego Luna , Daniel Gimenez Cacho Runtime 106 Minutes

While fans might not expect the Oscar-winning filmmaker behind Children of Men and Gravity to have delivered one of the best teen romances of the 2000s, Alfonso Cuarón found his own beautiful way of elevating the genre.

Y tu mamá también is a Mexican coming-of-age story starring Gael García Bernal and Diego Luna as two best friends who set out on a road trip with a woman in her 20s, both of them developing feelings for the older and charismatic woman. The movie is funny, sexy, and insightful with Cuarón’s beautiful directing and writing only making the intimate story all the more compelling.

The romance at the center of the movie is surprising with it taking some turns that audiences might not see coming. However, it is also a bittersweet story of young friendship with there being an inevitability of these two young men from different backgrounds drifting apart, which makes their time together and the changes their relationship takes all the more exciting.

Related 15 Best Teen Movies Directed By Women, Ranked By IMDb

There have been a plethora of successful female directors who have made a name for themselves with teen movies.

26 The Girl Next Door (2004)

A Studious Teen Falls For A Porn Star

The Girl Next Door R

The Girl Next Door (2004) is a coming-of-age romantic comedy directed by Luke Greenfield. The film stars Emile Hirsch as Matthew Kidman, a high school senior who falls for his new neighbor Danielle, played by Elisha Cuthbert. Their budding relationship takes a turn when Matthew discovers Danielle’s past as a porn star, leading to a series of comical and poignant events that challenge his understanding of love and life.

Release Date April 9, 2004 Cast Elisha Cuthbert , Emile Hirsch , Timothy Olyphant Runtime 1h 49m

Another movie inspired by a classic 80s romance, The Girl Next Door is a raunchy reimagining of the Tom Cruise breakout teen movie Risky Business. In this version, Emile Hirsch stars Matthew, an ambitious high school senior who forms a crush on his attractive next-door neighbor, Danielle (Elisha Cuthbert), only to find out that she is a porn star.

This sends him on an adventure in which he breaks out of his shell and lives more rebelliously thanks to Danielle. The movie received mixed reviews and poor box office upon its release but became a cult favorite years later. There is a lot of charm to the movie thanks to the romance that blossoms between the two leads.

While Matthew is made to be more adventurous, he also helps Danielle feel accepted in a world that judges her for her work. The movie also features a strong supporting cast that includes Paul Dano, Olivia Wilde, and Timothy Olyphant in a scene-stealing villainous role.

25 John Tucker Must Die (2006)

Four Girls Team Up To Bring Down Their Ex

John Tucker Must Die (2006) PG-13

John Tucker Must Die is a teen comedy film directed by Betty Thomas. The story follows three high school girls who learn they have been dating the same guy, John Tucker, and team up with a new girl to exact revenge. Their elaborate plan to bring him down takes unexpected turns, leading to humorous and insightful moments about relationships, popularity, and self-identity. The film stars Jesse Metcalfe, Brittany Snow, and Ashanti.

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*Availability in US Director Betty Thomas Release Date July 28, 2006 Cast Jesse Metcalfe , Brittany Snow , Ashanti , Sophia Bush , Arielle Kebbel , Penn Badgley Runtime 89 minutes

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.

Related 13 Coming-Of-Age Movies That Define Millennials

The 90s and 00s were the best eras for coming-of-age movies, and there are plenty of iconic movies that really captured growing up as a millennial.

24 Angus (1995)

A Bullied Kid Gets A Chance To Impress His Crush

Angus PG-13

Angus is a 1995 coming-of-age film directed by Patrick Read Johnson. The story follows Angus Bethune, a socially awkward teenage boy, who navigates the challenges of high school life and bullying while discovering his self-worth and courage. The film features performances from Charlie Talbert as Angus and Chris Owen as his best friend, Troy, against the backdrop of a school dance that could change everything for Angus.

Director Patrick Read Johnson Release Date September 15, 1995 Cast Charlie Talbert , George C. Scott , Kathy Bates , Perry Anzilotti , Robert Curtis Brown , Kevin Connolly , Tony Denman , Yvette Freeman Runtime 90 Minutes

See more : Who are Molly Smith Parents? Meet Frederick W. Smith

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

Bend It Like Beckham

Jess is an Indian teenager who lives in England and dreams of following in the footsteps of her idol, British footballer David Beckham. But her family has more traditional plans for her.

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*Availability in US Director Gurinder Chadha Release Date April 12, 2002 Cast Parminder Nagra , Keira Knightley , Jonathan Rhys Meyers , Anupam Kher , Archie Panjabi Runtime 112 min

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.

DID YOU KNOW:
Despite their characters being the same age, Parminder Nagra is 10 years older than Keira Knightley.

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

Edge of Seventeen TV-MA

Edge of Seventeen is a coming-of-age drama directed by David Moreton. Set in 1984, the film follows Eric Hunter, portrayed by Chris Stafford, as he navigates the complexities of adolescence, identity, and sexual orientation. With supporting performances from Tina Holmes and Andersen Gabrych, Edge of Seventeen explores the challenges and triumphs of growing up and coming out in a small Midwestern town.

Director David Moreton Release Date June 14, 1998 Cast Chris Stafford , Tina Holmes , Andersen Gabrych , Stephanie McVay , Lea DeLaria , John Eby , Antonio Carriero , Jason Lockhart Runtime 99 Minutes

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

Step Up PG-13

Tyler gets the opportunity of a lifetime after vandalizing a performing arts school, earning him the chance to win a scholarship and dance with a promising dancer, Nora.

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*Availability in US Director Anne Fletcher Release Date August 11, 2006 Runtime 98 minutes

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.

DID YOU KNOW:
Channing Tatum and Jenna Dewan were married in real life.

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 PG-13

Clueless is a 1995 comedy film that follows Cher Horowitz, a wealthy and popular high school student in Beverly Hills, who navigates adolescence while matchmaking friends and discovering her own feelings. The film offers a modern adaptation of Jane Austen’s novel Emma, set in a contemporary American high school.

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*Availability in US Director Amy Heckerling Release Date July 19, 1995 Cast Alicia Silverstone , Stacey Dash , Brittany Murphy , Paul Rudd , Donald Faison , Elisa Donovan , Breckin Meyer , Jeremy Sisto , Dan Hedaya , Aida Linares , Wallace Shawn , Twink Caplan , Justin Walker , Sabastian Rashidi , Herb Hall , Julie Brown , Susan Mohun , Nicole Bilderback , Ron Orbach , Sean Holland , Roger Kabler , Jace Alexander , Josh Lozoff , Carl Gottlieb , Joseph D. Reitman , Anthony Beninati , Micki Duran Runtime 97 minutes Expand

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 and Paul Rudd’s chemistry in the film is perfection among ’90s movies that include teenage romance.

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.

Related 15 Best Makeover Movies Like Clueless

Alicia Silverstone in Clueless is iconic. But if you need to quench your thirst for makeover movies, here are the best! Spoiler: it may involve Prada.

19 Get Over It (2001)

A Young Man Attempts To Win Back His Girlfriend

Get Over It PG-13

Get Over It is a teen romantic comedy directed by Tommy O’Haver. The film stars Ben Foster as Berke, a high school student who joins the school play in an attempt to win back his ex-girlfriend, played by Melissa Sagemiller. Kirsten Dunst co-stars as Kelly, Berke’s friend and potential new love interest, while Martin Short provides comic relief as the eccentric drama teacher.

Director Tommy O’Haver Release Date March 9, 2001 Cast Kirsten Dunst , Ben Foster , Melissa Sagemiller , Sisqó , Shane West , Colin Hanks , Zoe Saldana , Mila Kunis Runtime 87 Minutes

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

Drive Me Crazy

Nicole and Chase used to be best friends. The high school centenary dance is coming up, but Nicole is dumped and so is Chase. They strike up a relationship to catch up with their ex-partners.

Director John Schultz Release Date October 1, 1999 Cast Adrian Grenier , melissa joan hart , Stephen Collins , Mark Metcalf , Faye Grant , Susan May Pratt Runtime 91 min

Reminiscent of the ’80s rom-comCan’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

Save the Last Dance PG-13

Save the Last Dance is a romantic drama directed by Thomas Carter, starring Julia Stiles as Sara, a teenager who moves to Chicago after a family tragedy. There, she befriends Derek (Sean Patrick Thomas), who introduces her to hip-hop culture and dance. Both characters navigate personal challenges while exploring a deepening relationship amidst the backdrop of their respective worlds coming together.

Director Thomas Carter Release Date January 12, 2001 Cast Julia Stiles , Sean Patrick Thomas , Kerry Washington , Fredro Starr , Terry Kinney , Bianca Lawson Runtime 112 minutes

If there’s one glaring fault in the 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

See more : Najee Harris Ethnicity, What is Najee Harris’s Ethnicity?

Bring It On PG-13

As the newly elected captain of her high school’s award-winning cheerleading squad, Torrence Shipman aims to take her team to the top of the national championships — despite the challenges of a rival squad, choreography calamities, catty fellow cheerleaders, and romantic entanglements.

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*Availability in US Director Peyton Reed Release Date August 25, 2000 Cast Kirsten Dunst , Eliza Dushku , Jesse Bradford , Gabrielle Union , Clare Kramer , Nicole Bilderback , Ian Roberts Runtime 99 minutes

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.

There have been seven
Bring It On
movies to date.

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.

Related 10 Ways That Bring It On Still Holds Up Today

The 2000 cheerleading movie Bring It On was charming and fun when it was released, and the movie has aged well in many ways.

15 How To Deal (2003)

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

How To Deal PG-13

For Halley, love seems very strange. Her parents are divorced. Her mother isn’t dating and her father is seeing a younger woman. Halley’s sister Ashley is about to get married and doesn’t realize that her fiancé isn’t the man of her dreams. But when Halley meets Macon, she understands the true meaning of love.

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*Availability in US Director Clare Kilner Release Date July 18, 2003 Cast Mandy Moore , Allison Janney , Trent Ford , Alexandra Holden , Dylan Baker , Nina Foch Runtime 99 minutes

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

Keith PG-13

Keith is a high school drama directed by Todd Kessler, featuring Jesse McCartney as Keith and Elisabeth Harnois as Natalie. The film explores the evolving relationship between Natalie, a popular high school senior, and Keith, a mysterious new student who becomes her chemistry lab partner. As their bond deepens, Natalie discovers Keith’s hidden secrets, challenging her perceptions and priorities.

Director Todd Kessler Release Date September 13, 2008 Cast Elisabeth Harnois , Jesse McCartney , Margo Harshman , Ignacio Serricchio , Michael McGrady , Jennifer Grey , Michael O’Keefe , Ethan Phillips Runtime 95 Minutes

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

The Princess Diaries follows Mia Thermopolis, a teenager who discovers she is the heir to the throne of a European kingdom. The film explores her journey from an ordinary student to embracing her royal heritage, confronting the challenges and transformations this revelation brings to her life.

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*Availability in US Director Garry Marshall Release Date August 3, 2001 Cast Anne Hathaway , Julie Andrews , Heather Matarazzo , Caroline Goodall , Hector Elizondo , Robert Schwartzman , Erik von Detten , Patrick John Flueger , Sandra Oh , Mandy Moore , Sean O’Bryan , Kathleen Marshall , Kimleigh Smith , Mindy Burbano , Elizabeth Gudenrath , Bianca Lopez , Tamara Levinson , Lenore Thomas , Erik Bragg , Meredith Shevory , Anita Marie Curran , Cassie Rowell , Todd Lowe , Joe Unitas , Joel McCrary Runtime 115 minutes Expand

The movie brings to life the childhood dream of living a fairytale.

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 story of Mia is based on Meg Cabot’s books.

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.

Related 20 Best Quotes From The Princess Diaries

The Princess Diaries was a critical part of early 2000s pop culture, and many of its best quotes are still powerful today.

12 First Daughter (2004)

The Daughter Of The American President Attempts To Find Love

First Daughter PG

The president’s daughter goes to college and escapes the protection of the Secret Service, but her father places an agent undercover as a student to keep an eye on her. The two fall in love and their romance is threatened by her boyfriend’s secret identity.

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*Availability in US Director Forest Whitaker Release Date September 24, 2004 Cast Katie Holmes , Marc Blucas , Amerie , Michael Keaton , Margaret Colin , Lela Rochon Runtime 105 minutes

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

what a girl wants PG

After turning 17, Daphne Reynolds decides to make a radical decision: to go to England to find her father, whom she only knows from an old photo and who is unaware of Daphne’s existence. There, she finds a loving father, but faces problems when her liberal upbringing is confronted with the rigid customs of British education.

Director Dennie Gordon Release Date March 27, 2003 Cast Amanda Bynes , Colin Firth , Kelly Preston , Eileen Atkins , Anna Chancellor , Jonathan Pryce Runtime 105 minutes

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 made 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.

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Category: Entertainment