30 Great Movies Like 10 Things I Hate About You Ranked
Gil Junger's 1999 classic "10 Things I Hate About You" marked the end of a decade absolutely packed with teen movies. Like so many of its contemporaries, it adapts a classic text: William Shakespeare's "The Taming of the Shrew." When new guy Cameron (Joseph Gordon-Levitt) falls for image-obsessed Bianca (Larisa Oleynik), he's blocked by her father's strict rules: Bianca can only date when her independent sister Kat (Julia Stiles) does. Cameron enlists the help of bad boy Patrick (Heath Ledger), who agrees to date cantankerous Kat. Soon enough, however, everyone gets a bit more than they bargained for.
"10 Things I Hate About You" is a classic romantic comedy, but what sets it apart from the crowd is its grounding in reality. Both Kat and Bianca are subject to the judgments and pressures of others, while Patrick represents that age-old adolescent feeling of being unseen and misunderstood. Hungry for more teen flicks with this sort of intelligence? Then get your orthodontic headgear out and put an emo playlist on — we're taking you back to high school. These are the 30 greatest movies like "10 Things I Hate About You," ranked from best to worst.
Say Anything
No one knows teenagers like Cameron Crowe, the writer of "Fast Times at Ridgemont High" and writer-director of "Almost Famous." Crowe's directorial debut (which he also wrote) was 1989's "Say Anything," a romance between underachiever Lloyd Dobler (John Cusack) and class valedictorian Diane Court (Ione Skye). Lloyd comes from a working class background, while Diane lives a sheltered life. Her overprotective father Jim (John Mahoney) doesn't think Lloyd is good enough for her, and does everything he can to break them up. But Lloyd and Diane follow their hearts instead of others' expectations.
"Say Anything" is beloved for its mix of humor, drama, and sweetness. This has made it a classic rom-com and teen film, as well as the source of the frequently-spoofed "standing outside the window playing Peter Gabriel on a boombox" shtick. Both rom-coms and teen films exist in heightened spaces: Characters act in over-the-top ways, and often exist as archetypes. This film subverts those expectations. Others might see Lloyd and Diane as a nobody and a priss, but they're far more than those tired tropes. This is perhaps the movie's biggest legacy, which is evident in "10 Things I Hate About You" — it also situates high school drama in a grounded emotional place.
The Half of It
Alice Wu's "The Half of It" puts a modern spin on "Cyrano de Bergerac." Ellie Chu (Leah Lewis) is a small-town loner who makes money by writing other students' assignments. Paul (Daniel Diemer) enlists her help in penning love letters to his crush, Aster (Alexxis Lemire). But as she pretends to be Paul, Ellie falls for Aster herself. Everything comes to a head when Paul realizes Ellie isn't who he thinks she is, and Aster realizes the same of Paul.
Alice Wu made a name for herself with 2005's "Saving Face," which centers a Chinese-American woman struggling to come out to her traditional mother. Wu applies just as much skill to "The Half of It": Ellie is a three-dimensional character whose loneliness, fear of abandonment, and unexpected romantic feelings for Aster make her swing between distance and vulnerability. This celebrated film isn't as comedic as "10 Things I Hate About You," but it does explore the nature of truth and falsehood — Ellie coaches Paul on what Aster likes, much like Cameron does with Patrick — and centers around a character who secretly wants to tear her many emotional walls down. "The Half Of It" captures the longing of adolescence with a funny, gentle, and compassionate touch.
Booksmart
Olivia Wilde's directorial debut, "Booksmart" follows best friends Molly (Beanie Feldstein) and Amy (Kaitlyn Dever), who have sacrificed their high school social lives to study (and in Molly's case, ensure she gets into an Ivy League school). Finally, the night before graduation arrives — and Molly discovers, to her horror, that plenty of students who didn't abstain from partying have also gotten into top-tier schools. Disturbed to have wasted all this time studying instead of having fun, Molly and Amy set out to have an epic night before high school is over.
While "Booksmart" makes use of teen movie tropes — there's an epic party, a surprise connection with a jerk who's actually sweet, and a run-in with the authorities — it puts a unique twist on all of them. Moreover, like "10 Things I Hate About You," "Booksmart" benefits from a great cast with undeniable chemistry, particularly between Feldstein and Dever, whose relationship is the anchor of the film. It also blends comedy, drama, and realism: The teens of "Booksmart" look and sound like the teens of today, without feeling gimmicky. Perhaps that's what the best teen movies capture — something both specific and universal. "Booksmart" is set to be one such time capsule all generations can enjoy.
To All The Boys I've Loved Before
It was inevitable that streaming giants would try their hands at the teen movie genre, and Netflix found a goldmine with Susan Johnson's "To All the Boys I've Loved Before," based on Jenny Han's book of the same name. Lara Jean (Lana Condor) is a shy teenager prone to crushes on cute boys. She writes letters to these crushes, which she proceeds to lock away. But after stumbling upon these passionate notes, Lara Jean's younger sister decides to mail them out to their fantasy recipients — one of whom is Lara Jean's sister's ex. Lara Jean and another crush, Peter (Noah Centineo), pretend to date, so that said ex (and her sister) think the letter is a joke.
As reported by Variety, "To All the Boys I've Loved Before" was a big success for Netflix, quickly becoming one of its most-viewed original movies. It's not hard to see why: This film is a fizzy delight boasting great performances, a clever premise, and an Asian-American lead, which remains rare in the teen movie genre. "To All the Boys I've Loved Before" plays into familiar teen tropes like fake relationships and irritating siblings, but it does so with a fresh, witty script that explores what it means to translate your fantasy into reality.
The Edge of Seventeen
Kelly Fremon Craig made her directorial debut with "The Edge of Seventeen," which immediately joined the canon of high school films. Nadine (Hailee Steinfeld) is a 17-year-old loner who's living in the shadow of her popular older brother Darian (Blake Jenner) and the death of their beloved father a few years prior. Nadine's world gets smaller when Darian unexpectedly starts dating Krista (Haley Lu Richardson), her best (and only) friend. New feelings of loneliness and exclusion crop up, pushing Nadine to turn to her favorite teacher at school, Mr. Bruner (Woody Harrelson). But one kind teacher can only fix so much.
Similarly to "10 Things I Hate About You," "The Edge of Seventeen" explores how teenagers deal with grief. Nadine's high school drama is compounded by the absence of her father, the one person who understood her. His loss drives a wedge between her and her brother, who is trying to balance the demands of his social life with taking care of his family. Nadine's self-loathing captures a particularly adolescent blend of misery — nothing matters, everything is terrible, and everyone hates you — which Steinfeld perfectly embodies. This is the world of Kat in "10 Things I Hate About You": Dark and real, but not actually as solitary as it often feels.
Heathers
"What is your damage, Heather?" Winona Ryder exclaims in the 1989 teen classic "Heathers," which seeks to answer that very question: What is the damage impacting these characters? Veronica (Ryder) is part of her school's popular clique, alongside the Heathers: Heather Chandler (Kim Walker), Heather Duke (Shannen Doherty), and Heather McNamara (Lisanne Falk). She dreams of life outside this mean-spirited group, and finds an unexpected escape route with J.D. (Christian Slater), a new student with a chip on his shoulder and some unconventional ideas about how to take down the Heathers. Unfortunately (and hilariously), things soon spiral out of control.
"Heathers" became a cult classic that's still frequently quoted more than 30 years after its release. It did this by capturing high school's extreme emotions through outright violence and a heaping helping of satirical black humor. This one-two punch has influenced countless teen films, including "Jawbreaker" and "Mean Girls." At the time, though, such a dark look at adolescence was a risk: As Ryder recounted to Entertainment Weekly, her then-agent "literally got on her knees and begged [her] not to do [the movie]." That agent was wrong, as we now know: "Heathers" remains one of the best teen movies ever because of its biting insight into what it means to be a high school outsider and insider.
Love, Simon
Greg Berlanti's "Love, Simon," based on Becky Albertalli's novel "Simon vs. the Homo Sapiens Agenda," centers around Simon (Nick Robinson), a closeted teen living in Atlanta. He struggles to keep the truth hidden while juggling friends, family, and his developing feelings for an anonymous classmate with whom he's been chatting online.
"Love, Simon" is more of a dramedy than an outright comedy like "10 Things I Hate About You," but both movies deal with hidden identity. Simon is forced to live a double life: He puts out one face publicly to his family and friends, while wearing another privately when he chats with "Blue." This film is also a major milestone for teen cinema, as it's the first mainstream film to revolve around a gay teenage love story. It does so in a way that's compassionate and normalizing, as Simon is surrounded by friends and family who love and support him for who he is. Simon's crisis is real, but the film doesn't sensationalize it: He is portrayed as going through the same sort of self-actualization process everyone goes through at that age, whether it's about sexuality or not. No wonder critics and audiences both fell for this charming, sweet, and funny coming-of-age film.
The Breakfast Club
For many, John Hughes is the undisputed king of high school movies, and "The Breakfast Club" is his crowning achievement. This film focuses on five students from different cliques, who have to spend a Saturday in detention: princess-y Claire, (Molly Ringwald), nerdy Brian (Anthony Michael Hall), sports hero Andrew (Emilio Estevez), offbeat Allison (Ally Sheedy), and rebellious John (Judd Nelson). As the hours grind on, this band of misfits becomes a genuine group of friends, bound together by the pressures they feel from their parents and their shared frustration with authority, which arrives in the form of Principal Vernon (Richard Gleason).
"The Breakfast Club" has all the elements of a great teen movie: A charismatic cast of young stars with good chemistry, a killer soundtrack, and an emotional core. Who doesn't know what it feels like to be misunderstood? And who isn't acquainted with the desire to fit in, even as you struggle to hold onto your independence? "The Breakfast Club" captures this moment of longing and rebellion so well, it influenced movies like "Dead Poets Society," "Say Anything," and "Boyz n the Hood" — as director of the latter film John Singleton told Criterion, "The Breakfast Club" "gave [him] a template."
Dope
While many high school movies reinforce stereotypes of mean girls, jocks, and nerds, some are invested in subverting those roles. Writer and director Rick Famuyiwa's "Dope" centers around a group of teens not usually shown on screen: Black nerds. Malcolm (Shameik Moore) and his friends Jib (Tony Revolori) and Diggy (Kiersey Clemons) have a shared love of '90s hip hop. Their geeky lives get shaken up when they meet a drug dealer at a party and wind up accidentally stealing a bunch of ecstasy. Malcolm and his friends must offload the drugs without getting in trouble — or ruining his chances at getting into Harvard.
"Dope" combines humor and drama to tremendous effect, and puts people of color at the forefront of its story — something that remains frustratingly rare in Hollywood. Though things get wacky, at its heart, "Dope" is about the concerns so many teenagers have: Dating, going to parties, getting into mischief, and piecing together a picture of the future. It never fails to be both positive and realistic, addressing issues of race and class as deftly as it explores prom dates. Like "10 Things I Hate About You," this is a movie that stays grounded in the sort of truth any teenager (or former teenager) can recognize.
Easy A
Before she was Cruella or Gwen Stacy, Emma Stone was Olive, the 17-year-old protagonist of Will Gluck's "Easy A." Olive is an outsider who finds a surprising way to boost her popularity: She lies about losing her virginity. After her social status skyrockets, she pretends to hook up with dorky guys in exchange for gift cards and popularity perks. As rumors of Olive's "promiscuity" spread, she leans into the Hester Prynne vibe — but things soon get out of hand. Before long, Olive finds herself the pariah of her school.
"Easy A" was a star-making turn for Emma Stone, who combines awkwardness, charisma, humor, and insecurity into one unforgettable teen heroine. Like "10 Things I Hate About You," this film draws from old source material — in this case, a loose interpretation of Nathaniel Hawthorne's "The Scarlet Letter" — which it brings into the teen comedy space. In high school movies, sex is often black or white, especially when it comes to young women. What sets "Easy A" apart is its gray area. Olive wavers between being celebrated for her sexuality and punished for it, and dauntlessly attempts to navigate her own desires in spite of everyone else's judgments. Add in a smart script and a brilliant cast — how wrong can things be if Lisa Kudrow, Patricia Clarkson, and Stanley Tucci are the adults in your world? — and you've got one of the most enjoyable teen flicks of the 2010s.
The Perks of Being a Wallflower
Writer and director Stephen Chbosky finally brought his beloved 1999 novel, "The Perks of Being a Wallflower" to the big screen in 2012. Charlie (Logan Lerman) is a depressed teenager who's dealing with the death of a close friend and trauma from his childhood. Though he starts from a place of isolation, Charlie begins to open up as he befriends the free-spirited Sam (Emma Watson) and her brother Patrick (Ezra Miller), who's in a secret relationship with another boy. Charlie is flooded with exciting emotions as he embraces these two new people, but as grows, he's also forced to confront things he's been trying to keep hidden.
"The Perks of Being a Wallflower" is a funny, real look at adolescent mental health. Charlie struggles with depression and PTSD, which are not often portrayed in a complex or serious way in high school dramedies. That alone makes this a must-watch for any fan of coming-of-age movies. The film is further bolstered by its three leads: Lerman, Watson, and Miller shine as three disparate characters who give each other different things. Together, they form a whole in a way that feels specific to high school, that age when so many people find their "tribe."
Mean Girls
If every generation has its iconic teen movie, you'd be hard-pressed to find a better choice for the 2000s than Mark Waters' "Mean Girls." Penned by Tina Fey and based on Rosalind Wiseman's book "Queen Bees and Wannabes," "Mean Girls" is about Cady (Lindsay Lohan), a newcomer to American high school. She and fellow outsiders Janis (Lizzy Caplan) and Damian (Daniel Franzese) decide to take down the Plastics, their school's most popular girls: Karen (Amanda Seyfried), Gretchen (Lacey Chabert), and queen bee Regina George (Rachel McAdams). Though Cady infiltrates the Plastics, things don't go according to plan once she finds the view is actually much nicer from the top.
Tina Fey's brilliant script captures the feeling of being both an outsider and a member of the inner circle. Power is alluring, and unless you're willing to "totally stab Caesar," you'll pay a hefty price to stay in the spotlight. "Mean Girls" hits all the marks: High school archetypes of popular girls, dumb jocks, and loner outsiders; a script that's quotable from beginning to end; and a cast of future stars like Amanda Seyfried and Rachel McAdams. "Mean Girls" spawned a musical, a sequel, and infinite gifs and memes, proving that when it comes to the legacy of this teen film, "the limit does not exist."
Clueless
Amy Heckerling's 1995 classic, which loosely adapts Jane Austen's "Emma," follows Cher Horowitz (Alicia Silverstone), a beautiful, popular, Beverly Hills-born "virgin who can't drive," who just wants to, like, do "stuff for other people." Cher decides to give a makeover to clueless new girl Tai (Brittany Murphy) and bring her under her wing, all while trying to manage her grades, hang with her best friend Dionne (Stacey Dash), and deal with her annoying stepbrother, Josh (Paul Rudd). As Cher goes on this journey of selflessness and self-discovery, she realizes that perhaps Tai isn't the clueless one after all.
If "10 Things I Hate About You" took a paternity test on "Maury," there's no doubt that "Clueless" would be identified as the father. "Clueless" draws from a classic text, mixes satire, genuine emotion, and charm, and features a beautiful cast of future stars. While Cher's outfits alone have influenced countless films and humans worldwide, Cher herself is the beating heart of this film. Sure, she's spoiled and entitled, but she's also kind, well-intentioned, funny, and perhaps most importantly, unique. It's hard to remember a world in which "ugh, as if" and "whatever" didn't exist, and that's all thanks to Cher and Alicia Silverstone.
Grease
You can't talk about high school movies without mentioning "Grease." Released in 1978, "Grease" takes place in 1958, and follows bad boy greaser Danny (John Travolta) who falls for innocent new girl Sandy (Olivia Newton-John). Being googly-eyed in love doesn't do much for Danny's cool kid reputation, so he pretends to be uninterested, leading to heartbreak, tension, and the most iconic black leather getup of the silver screen (sorry, Catwoman). Danny struggles to decide whether to be himself or the person others expect him to be, while Sandy has to reconcile her innocence and naivete with her own desires for love and popularity.
"Grease" is one of the highest-grossing live-action musicals of all-time, and has been a cultural touchstone for decades. A big part of what makes it so long-lasting is the complex '70s sensibility it applies to the shiny '50s, which simultaneously captures two now-lost eras. This doesn't make it dated, either: "Grease" transcends time through its eternal story of young love, peer pressure, and the joys of music. In this, it fits right alongside "10 Things I Hate About You," which finds timelessness in teen angst.
Ferris Bueller's Day Off
Following "The Breakfast Club," John Hughes struck teen gold again with 1986's "Ferris Bueller's Day Off," which he wrote, directed, and produced. "Ferris Bueller's Day Off" invites viewers into the life of Ferris (Matthew Broderick), who decides to play hooky one fine spring day. After convincing his patient girlfriend Sloane (Mia Sara) and hypochondriac best friend Cameron (Alan Ruck) to join him on his day of fun, they steal Cameron's strict father's Ferrari and adventure around Chicago. The whole time, they try to avoid being caught by their parents or Ed Rooney (Jeffrey Jones), the school dean, who is determined to catch his number one truant.
"Ferris Bueller's Day Off" brings audiences directly into the mind of the charming and charismatic Ferris, who consistently breaks the fourth wall to comment on the day's events. The movie's fun conceit — a group of teens skip school and go on adventures — masks its deeper theme: Ferris is trying to help Cameron find some freedom and self-respect. As in other Hughes movies, adults abuse their authority here, and Cameron's father is a particularly egregious culprit. He cares far more about his vintage car than his son. Thus, Ferris attempts to take care of his friend the way his father doesn't, and guide him towards self-realization. After all, "life moves pretty fast. If you don't stop and look around once in a while, you could miss it."
Fast Times at Ridgemont High
It's not surprising that "Fast Times at Ridgemont High" is a teen classic: It was the directorial debut of Amy Heckerling ("Clueless") and written by Cameron Crowe ("Say Anything"), who based it on his book about spending a year undercover at an American high school. This ensemble film looks at the lives of many different students: Stacy (Jennifer Jason Leigh), a sophomore looking to lose her virginity who gets more than she anticipated; Brad (Judge Reinhold), Stacy's older brother, who struggles to keep a job and his girlfriend; Linda (Phoebe Cates), Stacy's friend, who helps guide her into her newfound sexuality; and Spicoli (Sean Penn), a stoner who's at odds with his history teacher.
"Fast Times at Ridgemont High" has stayed culturally relevant thanks to its memorable dialogue (Sean Penn may have singlehandedly put "dude" into the vernacular) and risqué attitude. But perhaps its most significant legacy is the realism and seriousness it applies to its characters. In Heckerling and Crowe's hands, this teenage world is treated tenderly and with respect, so that storylines like Stacy's decision to get an abortion are told without shame. This open and thoughtful approach has left a tremendous legacy in the teen movie genre, visible in plenty of films on this list.
Romeo + Juliet
Although Baz Luhrmann's "Romeo + Juliet" doesn't share the high school comedy space "10 Things I Hate About You" occupies, the film's modernization of Shakespeare and representation of star-crossed lovers makes it essential viewing for any fan. Romeo (Leonardo DiCaprio with his best haircut to date) is a sensitive soul, who falls for the gentle Juliet (Claire Danes). What could be a simple love affair is complicated by the fact that Romeo and Juliet's families are locked in a vicious feud. Romeo and Juliet try to find a way to make it work, but ultimately, the forces of fate lead their relationship to its tragic end.
"Romeo + Juliet" is peak Baz Luhrmann, with its hyper visual style, bold colors and production design, and epic soundtrack. The script retains Shakespeare's text, and both DiCaprio and Danes sell it. Adolescence is a time of big emotions, and no one embodies that better than Romeo and Juliet, which means it feels natural to watch these teenagers make sweeping declarations of love, even though they just met. The chemistry between DiCaprio and Danes helps in this regard, though it's just one part of the film's excellent cast, which includes Harold Perrineau as Mercutio and John Leguizamo as Tybalt.
Romy and Michele's High School Reunion
Best friends Romy (Mira Sorvino) and Michele (Lisa Kudrow) are 28, single, and don't yet know what they want to do with their lives. With their 10-year high school reunion coming up, they decide to impress their classmates by pretending to be more successful than they are. This is all happening before social media, so who's going to know? They arm themselves with the perfect lie — they invented Post-Its — and set out to impress everyone who tormented them in high school. But things don't go according to plan, and that's exactly what makes "Romy and Michele's High School Reunion" a classic.
Although Romy and Michele are adults, they still get caught in the classically adolescent tension between being yourself and the person others believe you to be. Fortunately, the titular duo has the type of friendship that gets people through their teen years and beyond. Kudrow and Sorvino play this bond to perfection: While Romy is concerned with what others think, Michele is unaware that their high school experience was lacking, because she had such a blast with her best friend. Whether you're the Mary or the Rhoda, "Romy and Michele's High School Reunion" is for anyone who's felt like it's them and their best friend against the world. Plus, it's filled with amazing one-liners and an all-star cast including Janeane Garofalo and Alan Cumming.
13 Going on 30
Gary Winick's "13 Going On 30" puts a female twist on "Big." It's 1987, and 13-year-old Jenna Rink (Christa B. Allen) invites her school's popular clique to her birthday party. The mean girls show up and humiliate her, leaving Jenna to wish that she were "30, flirty, and thriving." Jenna's wish comes true: She wakes up the next day in 2004 at the age of 30 (now played by Jennifer Garner). Though she has no memory of the past 17 years, she quickly discovers she's a successful, mean-spirited fashion editor. The 13-year-old who lives in her body must take control and turn this life into something filled with fun, laughter, and love with her old friend Matty (Mark Ruffalo).
"13 Going on 30" hinges on Jennifer Garner, who shines as an adult playing a kid who is pretending to be an adult. Adolescence can be a time of pretense, as many teenagers try to act older than they are. But ultimately, they're still kids, and Garner navigates this tension perfectly. "13 Going on 30" is ultimately about the loss of one's inner child over the course of maturation. Happily, Jenna reclaims her youthful spirit, much like Kat discovers how to let go and have fun in "10 Things I Hate About You."
Bring It On
Peyton Reed's "Bring It On" dives deep into the complex world of competitive cheerleading. Newly-appointed cheer captain Torrance (Kirsten Dunst) is in over her head — especially after she realizes the former captain of her championship-winning squad stole routines from the Clovers, a predominantly Black team from Compton led by Isis (Gabrielle Union). Torrance struggles to find a new routine, all while juggling blossoming feelings for a guy who isn't her boyfriend and an escalating rivalry with the Clovers.
"Bring It On" is a mix of teen comedy, outright parody, and socially-conscious drama. Kirsten Dunst is the anchor, deftly shifting between bubbly cheer queen and serious leader. This keeps the film together as it jumps between wacky dance routines and the very real injustice done to the Clovers, with occasional forays into goofball comedy. Although the film got mixed reviews when it debuted, its blend of humor and commentary has made it a cult hit. In this, "Bring It On" proves that teen flicks don't have to be shallow — a point Kat Stratford would doubtlessly appreciate.
The Girl Next Door
Luke Greenfield's "The Girl Next Door" follows Matthew (Emile Hirsch), a high schooler who becomes infatuated with his new neighbor, Danielle (Elisha Cuthbert). Matthew is studious and Georgetown-bound, but as he's only really hung out with sex-obsessed Eli (Chris Marquette) and awkward Klitz (Paul Dano) for four years, he hasn't really made any memories. Matthew and Danielle quickly connect, but their romance hits a snag when Matthew discovers that Danielle is a former adult film actress. When he can't let go of the past she's trying to leave behind, she leaves him. Matthew must try to regain her trust and get her back.
"The Girl Next Door" is a surprisingly sweet film about two people trying to discover who they are outside of others' expectations. Matt is scared to explore life beyond good grades, while Danielle struggles to be taken seriously as a person and not just a fantasy figure. These two lonely people see each other for who they really are, which is at the heart of any love. Plus, the cast is a who's-who of stars like Paul Dano, Olivia Wilde, and Timothy Olyphant.
Never Been Kissed
Raja Gosnell's "Never Been Kissed" sends an adult Drew Barrymore back to high school. Josie Geller (Barrymore) is an introverted 25-year-old journalist who's never had a serious relationship. When her editor sends her undercover to a high school to write an exposé on the lives of teenagers, she's offered something of a do-over: Josie's high school experience was miserable. While she initially stumbles in her undercover role, she eventually creates a new self, thanks to the guidance of her cool older brother Rob (David Arquette) and her English teacher, Mr. Coulson (Michael Vartan).
While "Never Been Kissed" is a by-the-numbers high school rom com, it also stands apart as it looks unblinkingly at the heartbreak of being bullied. Josie is a lonely character who just wants connection, but high school foiled her at every turn. How can she find love when her experiences have only told her that her real self isn't good enough? Indeed, "I'm not Josie Grosie anymore!" is a mantra for all who suffered at the hands of closed-minded people. Watching Josie go on a journey of self-acceptance is funny, heartwarming, and memorable enough that Barrymore reprised the role for a sketch on "The Drew Barrymore Show."
The Princess Diaries
Based on the Meg Cabot novel of the same name, "The Princess Diaries" centers around Mia Thermopolis (Anne Hathaway in her breakout role), a dorky teenager who discovers she's the sole heir to the tiny European nation of Genovia. Clarisse (Julie Andrews), her refined grandmother, grooms the shy, introverted Mia into a glamorous princess and teaches her how to tap into a newfound confidence. But she and Mia have very different ideas about what royalty and power should look like.
"The Princess Diaries" was a surprise hit, considering it starred then-newcomer Anne Hathaway: The film grossed $165 million worldwide. It has since become a teen classic, thanks in large part to Hathaway's performance and the chemistry she shares with Andrews and Heather Matarazzo, who plays Mia's quick-witted best friend Lilly. "The Princess Diaries" is also notable for its genuine depth: It tells the story of a young woman who is bombarded with ideas of who she should be and why. Mia stands out among teen heroines as she not only figures out who she is, but also how she can be of service to others with her newfound power. Kat Stratford would be proud.
Deliver Us From Eva
After appearing in a supporting role in "10 Things I Hate About You," which famously draws from Shakespeare's "The Taming of the Shrew," Gabrielle Union took the lead in Gary Hardwick's "Deliver Us From Eva," a 2003 adaptation of the same text. Union plays Eva, who's controlling and bossy both by nature and nurture: Her parents died when she was quite young, which made her responsible for her three sisters. As an adult, she oversteps by meddling in their lives, which leads their boyfriends to hire Ray (LL Cool J) to date Eva so she'll back off.
While "Deliver Us From Eva" isn't a teen film, it's enormously similar to "10 Things I Hate About You" in that it modernizes Shakespeare and features Union. She shines brighter than ever before as a domineering, charming, and weary woman who lets her perfectionist mask fall as she becomes closer to Ray. Although the film got mixed reviews, people who love rom-coms (especially the "romantic bet" sub-genre), sparkling casts, and strong heroines are sure to enjoy it. "Deliver Us From Eva" can be somewhat by-the-book with its plot points, but thanks to Union, LL Cool J, and supporting turns from Meagan Good, Essence Atkins, and Kym Whitley, this film remains a fun and charming romp.
She's The Man
Teen movies can't get enough of Shakespeare — perhaps because high school is when so many people first encounter the Bard. Andy Fickman's "She's The Man" furthers this tradition by putting a 2006 spin on "Twelfth Night." Viola (Amanda Bynes) is a star soccer player who is devastated when her school cuts the girls' soccer team. Her twin brother Sebastian (James Kirk) is supposed to start at a new boarding school, but ends up traveling the world instead. Thus, Viola pretends to be Sebastian and join his school's soccer team. Things take a confusing turn when star player Duke (Channing Tatum) befriends "Sebastian" and asks him for help in wooing another girl. Unfortunately, that girl falls for "Sebastian" instead.
"She's the Man" brings Shakespeare to a slapstick and somewhat predictable place. But thanks to Amanda Bynes, who manages to play two roles at once that both navigate murky waters of lies and identity, the movie works. One can't even fault 26-year-old Channing Tatum for pretending to be a high schooler here — what are teen movies if not showcases for 20-somethings? Just ask Rachel McAdams, who was 26 in "Mean Girls." It's a strange delight to watch Tatum become confused by "Sebastian's" awkward attempts at masculinity. "She's the Man" brings a lot of laughs and a bit of heart to the teen comedy genre.
She's All That
1999 was a watershed year for teen movies: Audiences were treated to "10 Things I Hate About You," "Cruel Intentions," "Jawbreaker," and more. Robert Iscove's "She's All That" joined the list by bringing George Bernard Shaw's "Pygmalion" to a pre-millennium audience. After getting dumped, popular guy Zack (Freddie Prinze Jr.) makes a bet that he can turn any girl in school into a prom queen within a few weeks. He and his buddies pick Laney (Rachael Leigh Cook), a loner art student, as their target. Zack proceeds to introduce Laney to the world of fashion, popularity, and parties, while she teaches him what it means to be a self-aware and emotional human being.
"She's All That" is similar to "10 Things I Hate About You" in that Zack masks his ulterior motives with Laney, much like Patrick does to Kat. While the movie has come under fire in recent years for its most ridiculous conceits — Laney's "makeover" amounts to taking her glasses off — it remains fondly remembered among many millennial viewers for its excellent cast, classic moments (including a hacky sack performance art scene), and hit-filled soundtrack.
But I'm A Cheerleader
Jamie Babbit's 1999 classic "But I'm A Cheerleader" explores the extreme ways teenagers are forced into socially-acceptable "normalcy." Megan (Natasha Lyonne) is a 17-year-old cheerleader who doesn't love kissing her boyfriend but does love Melissa Etheridge. Megan's family concludes she's a lesbian and must be "cured," so they send her to a conversion therapy camp. Here, Megan meets Graham (Clea DuVall), who is about to be disowned by her family. Megan is initially eager to be indoctrinated by the camp, but ultimately realizes she's powerless to deny who she is and who she loves.
"But I'm A Cheerleader" wasn't well-received by critics, but that hardly matters: It's become a much-lauded cult hit in the years since it hit theaters. While it is a campy satire, it also has an intense emotional core. Megan wholeheartedly believes she's straight, and when she discovers she isn't, she's devastated. Her journey to ecstatic self-acceptance is as moving as it is hilarious. This film stands out as a unique teen story which mines all-too-real injustice for sardonic humor and stirring emotion.
Can't Hardly Wait
Deborah Kaplan and Harry Elfont's "Can't Hardly Wait" takes viewers on a roller coaster ride through an epic graduation party. Preston (Ethan Embry), a shy, sweet guy, wants to finally confess his feelings to his crush of four years, the popular Amanda (Jennifer Love Hewitt). Snarky Denise (Lauren Ambrose) finds herself accidentally locked in a bathroom with her sex-obsessed former friend Kenny (Seth Green). William (Charlie Korsmo) decides to enact revenge on his bully, Mike (Peter Facinelli), but gets sidetracked by alcohol and Guns N' Roses instead.
"Can't Hardly Wait" is made up of teen movie tropes like epic house parties, musical interludes, and opposites attracting. While you're doubtlessly familiar with all of these elements, the characters have a bit more weight than you might expect, courtesy of actors like Embry and Ambrose, who infuse them with bite and empathy. "Can't Hardly Wait" taps into the same fun "10 Things I Hate About You" embodies (which also features an epic party scene). This makes it an easy and joyful experience for any fan of the teen genre.
Not Another Teen Movie
Given the seemingly infinite number of teen movies made in the '90s, it was really only a matter of time before someone parodied all of them. Joel Gallen took on this task with 2001's "Not Another Teen Movie." The main storyline is that of "She's All That:" Jake (Chris Evans) gets dumped by his cheerleader girlfriend (Jaime Pressly) and makes a bet that he can turn anyone into prom queen, even geeky Janey Briggs (Chyler Leigh). Jake and Janey encounter all the necessary teen movie tropes — an epic party, revelations about families and feelings, and a potential love triangle with Janey's best friend — as they fall for each other, paint-covered overalls and all.
No teen film is spared spoofing, from "American Pie" to "Pretty in Pink." This includes "10 Things I Hate About You": "Not Another Teen Movie" parodies its grand gesture scene when Jake sings "Janie's Got a Gun" to win Janey back. While certain elements of it are dated (like white characters pretending to be Asian), it remains a hilarious takedown of beloved tropes and archetypes. It also features then-up-and-coming stars like Chris Evans and Chyler Leigh, and brings classic teen stars like Melissa Joan Hart, Lacey Chabert, and the ultimate teen queen, Molly Ringwald, into the mix.
Drive Me Crazy
John Schultz's "Drive Me Crazy" centers around type-A Nicole (Melissa Joan Hart) and slacker Chase (Adrian Grenier), who decide to fake a relationship to make their love interests jealous. Naturally, Nicole has to give Chase a makeover so that both her crush and Chase's ex-girlfriend (Ali Larter) will get appropriately jealous, even though, like Laney in "She's All That," he's absurdly attractive as is. But as these two former friends fake romance for all the world to see, they discover there might be something not completely fake between them.
"Drive Me Crazy" takes its name from the famous Britney Spears song, which is featured on its soundtrack. Both Hart and Grenier appear in the song's music video, which is likely more well-known than the movie itself. Although aspects of the film fall flat, its opposites-attract storyline remains fresh and fun, as does the chemistry between its two leads. As Hart recalled to Today, this was Adrian Grenier's first mainstream movie: "He's coming into this kind of pop culture movie and I was kind of queen of pop culture TV at the time ... We had a really good time together." "Drive Me Crazy" may not be as strong as other teen movies, but it still boasts engaging young stars, an endearing relationship, and a classic Britney Spears song.