This 90s rendition of The Taming of the Shrew features the quintessential elements of a teen rom-com; a star-studded cast, romantic hoodwinks, and Heath Ledger’s performance of “Can’t Take My Eyes Off You” backed by a high-school marching band.
The film tells the story of two sisters whose overbearing doctor father has one rule; his daughters are not allowed to date. His younger daughter, Bianca (Larissa Oleynik), is the school’s queen bee and the locus of attention for the guys.
Desperate to date, Bianca strikes a deal with her father; she may date if Kat (Julia Stiles), her ‘shrew’ sister, has a date too.
Cameron James (Joseph Gordon-Levitt) has his heart set on dating Bianca. With the help of his nerdy friend Michael (David Krumholtz), they hatch a scheme to convince the pretty boy, Joey Donner (Andrew Keegan), to hire Patrick Verona (Heath Ledger) to date Kat.
The problem is that Patrick is a cigarette-smoking, bird-eating ruffian, and Kat is an angry feminist who would rather do anything than go out with him.
10 Things I Hate About You boasts an array of conformist and nonconformist characters instead of typical teen movie archetypes. Furthermore, the gender balance and storyline appeal to a range of moviegoers.
She’s All That
The complex love triangles between polar opposite characters in 10 Things I Hate About You are mirrored in She’s All That. This modern adaptation of Pygmalion depicts a bargain centered around a cutthroat prom election and a Cinderella transformation.
Siler (Freddie Prinze Jr.), the high school hunk, is rejected by his prom queen sweetheart, Taylor Vaughan (Jodi Lyn O’Keefe), who fell for a washed-out TV soap star she that met over spring break.
Zack justifies his heartache after being publicly dumped by claiming that Taylor is all make-up and wonder-bra and that he can turn any girl into a prom queen.
Following this comment, his high-school pal, Dean Sampson (Paul Walker), challenges him to a wager and chooses the geeky-looking Laney Boggs (Rachael Leigh Cook) from the crowd as the duckling Zack must transform into a swan.
However, as Laney transforms into the perfect prom queen, Zack begins to fall for her.
This film is a classic teen rom-com that is guaranteed to have audiences reminiscing over the agonizing teen angst that high school brings.
A Knight’s Tale
Inspired by ‘The Canterbury Tales,’ this period piece stars Heath Ledger as the peasant-born protagonist who bamboozles his way to win the heart of a fair Lady Jocelyn (Shanynn Sossamon) and a reputation of a legendary knight.
William (Ledger), a young squire with a talent for jousting, sets out on the road with his companions (Mark Addy, Alan Tudyk) when his master dies unexpectedly. They meet a writer named Chaucer (Paul Bettany) along the way, who William persuades to falsify genealogical records to pass himself off as a knight.
With his newly acquired knowledge, William sets out to show himself a worthy knight in the country’s jousting championship, and along the way, he discovers romance.
If you enjoyed watching the charming Heath Ledger win over the heart of a strong female character who, much like Kat, challenges the protocols governing what a fair maiden should be. Both 10 Things I Hate About You and A Knight’s Tale have plots centered around deception that captivates audiences using dramatic irony.
Clueless is a Beverly Hills rendition of Jane Austen’s Emma. This cult classic depicts Cher Horowitz (Alicia Silverstone), who is shallow, wealthy, and socially successful, is at the top of her Beverly Hills high school’s pecking order.
Encouraged by her success as a self-proclaimed cupid and all-around life coach, Cher decides to give Tai (Brittany Murphy), a hopelessly klutzy new pupil, a makeover.
However, this Cinderella transformation is followed by a whirlwind of romantic turmoil. As Cher tries to restore order to her seemingly perfect life, she discovers that her disapproving ex-stepbrother (Paul Rudd) was right about how misguided she was, and she falls for him.
Tai’s transformation from a duckling into a swan and Cher’s inner journey to becoming less grounded in superficial ideals is comparable to the character arcs in 10 Things I Hate About You. Like Cher, Patrick realizes that a deeper connection is priceless.
She’s the Man
Inspired by Shakespeare’s play Twelfth Night, She’s the Man is a teen romantic comedy that features a feisty Viola Hastings (Amanda Bynes) who, disguised as her twin brother, hoodwinks her way into Illyria Prep, where she can join the boys’ soccer team.
Regrettably, she had not anticipated falling in love with her roommate Duke (Channing Tatum). Duke, on the other hand, has his sights set on Olivia (Laura Ramsey). What makes matters worse is Olivia’s growing attraction to the counterfeit Sebastian.
If things weren’t already complicated enough, the real Sebastian (James Kirk) arrives home early from London to discover that his twin sister has taken his place. The romantic pandemonium and clever deception create powerful dramatic irony that captivates audiences.
Many of the characters in 10 Things I Hate About You are mirrored in She’s the Man. Both Kat and Viola are strong female protagonists that challenge the expectations placed on young women.
How To Lose a Guy in 10 Days
While How to Lose a Guy in 10 Days explores more adult relationships than 10 Things I Hate About You, both films use romantic deception to create humor and intrigue.
The playful love-hate relationship between Andie (Kate Hudson) and Ben (Matthew McConaughey) mirrors the relationship between Kat and Patrick.
In her latest piece about how to get a guy to leave you in 10 days, Andie Anderson (Kate Hudson), an advice columnist, seeks to push the boundaries of what she can write about.
Her editor, Lana (Bebe Neuwirth), adores her spunky approach to love and challenges Andie to locate a man for the experiment.
Simultaneously, executive Ben Berry (Matthew McConaughey) is so sure of himself that he believes he can make any lady fall in love with him in just ten days.
Ben’s boss, Phillip (Robert Klein), takes him up on his claim and wagers that he will grant Ben the opportunity to lead a coveted diamond campaign if he can achieve this.
However, Andie and Ben’s preparations fail the moment they meet.
The Duff shares several parallels with 10 Things I Hate About You; complicated love triangles, a high school hierarchy, and ultimately realizing that genuine connection triumphs overall.
Bianca Piper (Mae Whitman) is a happy high school senior sent down a spiral when she discovers that her prettier, more popular classmates refer to her as ‘The DUFF’ (Designated Ugly Fat Friend). Despite her favorite teacher’s warnings, she ignores the potential distraction of her infatuation, Toby (Nick Eversman).
She enlists the aid of Wesley (Robbie Amell), a slick but charming jock, to help her reinvent herself.
To save her senior year from total disaster, Bianca must have the courage to defeat it-girl Madison (Bella Thorne) and remind everyone that we are all someone’s DUFF, no matter how we appear or act.
Never Been Kissed
If the tension created by the carefully curated sham in 10 Things I Hate About You had you at the edge of your seat, you will fall in love with this romantic comedy that follows a young reporter posing as a high school student to gain insight into the lives of teenagers. However, she discovers more than what she set out to.
Josie Gellar (Drew Barrymore), a Chicago Sun-Times copy editor anxious to advance from copy editor to reporter, gets her opportunity when her boss orders her to go undercover to investigate the high school scene.
Josie, a disgruntled former high school geek, is transformed into a popular queen bee by her high school dropout brother Rob Geller (David Arquette).
This bamboozle allows both Josie and Rob to rediscover love and the delights of youth. Josie catches the eye of Sam Coulson (Michael Vartan), a charming and sweet English teacher.
However, as Josie’s publishing deadline approaches, the cost of blowing her cover grows increasingly frightening. She must choose between her dream job and her dream man.
Down to You
Complex romantic relationships, many obstacles, and big romantic gestures make Down to You a more grown-up rendition of 10 Things I Hate About You. Furthermore, this film stars Julia Stiles as a spunky female protagonist who dares to challenge the conventional role of a female love interest.
The son of a renowned chef (Henry Winkler), Al (Freddie Prinze Jr.), and Imogen (Julia Stiles), a gifted artist, fall in love the moment they lock eyes in New York City.
However, the path to happiness is riddled with obstacles; a looming engagement, an opportunistic porn actress (Selma Blair), and Jim Morrison (Ashton Kutcher) threaten to tear the young lovers apart before their passion can blossom fully.
Failure to Launch
35-year old Tripp (Matthew-McConaughey) has the whole package; a fantastic career, a cool car, a passion for sailing, and a wonderful house. His only problem is that he still lives with his parents. Desperate for their son to fly the nest, Al (Terry Bradshaw) and Sue (Kathy Bates) hire professional help.
Paula (Sarah Jessica Parker), an “interventionist,” has a recipe for these situations and tries to launch Tripp toward adulthood. However, her formula is put to the test when she begins to develop feelings for Tripp.
Like in 10 Things I Hate About You, a web of lies steadily spirals out of control to create a nail-biting plot. Although this romantic comedy graduates from the typical teen drama, it still carries as many big romantic gestures, agonizing crushes, and painfully awkward moments that will leave you in fits of laughter.
For three years, Andrew Paxton (Ryan Reynolds) has been working as Margaret Tate’s (Sandra Bullock) assistant at a New York publishing house. Margaret, a Canadian, devises a plot to marry Andrew to avoid deportation due to an expired visa; he accepts, provided she promises a promotion.
On Monday, an INS agent pledges to put the pair to the test regarding each other.
Margaret joins Andrew on his trip home to Sitka, Alaska, for his grandmother’s 90th birthday celebrations. The following few days are dominated by family dynamics: conflicts between Andrew and his father, an ex-girlfriend, Andrew’s hatred of Margaret, and her history color the next few days, with the INS preparing to prosecute Andrew with fraud.
Two Weeks Notice
Lucy Kelson (Sandra Bullock) is a hardworking Harvard-educated lawyer who uses her profession and passion for promoting social justice. However, she uses her work as a suit of armor to protect her heart from breaking.
Playboy George Wade (Hugh Grant) is the dashing public face of the Manhattan-based Wade Corporation, a development firm Lucy frequently opposes.
Needing a more qualified lawyer, George offers Lucy the job of his legal counsel. She accepts, on the condition that George promises that his firm will not demolish a community center near her childhood Coney Island home.
However, his never-ending list of demands pushes Lucy to quit and give George two weeks’ notice. As Lucy searches for someone to take her place at the firm, she finds more than just her replacement.
The theme of ‘opposites attracts’ apparent in 10 Things I Hate About You is also present in Two Weeks Notice. Furthermore, the playful love-hate dynamic between Lucy and George mirrors the relationship between Kat and Patrick.
Just Like Heaven
An unmarried and overworked doctor, Elizabeth (Reese Witherspoon), is passionate about her job but can’t seem to find time for a life outside of work.
David (Mark Ruffalo) is a struggling widow whose only concerns are a cold beer and a comfortable sofa. A tragedy turns Elizabeth’s life upside down and leads to an unlikely connection.
While the plot of this film may not be centered around deception, it shares several qualities with 10 Things I Hate About You. Both Elizabeth and Kat are strong, independent female characters.
Furthermore, the banter between Elizabeth and David parallels Kat and Patrick’s love-hate relationship.
Drive Me Crazy
Nicole (Melissa Joan Hart) and Chase (Adrian Grenier) may have grown up next door to one another, but they could not be more opposite. They put their differences aside when they devise a scheme to date each other to make their respective love interests jealous.
However, Nicole and Chase soon discover that the love of their lives is closer than they ever imagined.
10 Things I Hate About You and Drive Me Crazy share several themes and plot lines. In both films, polar opposite characters are drawn together by a carefully planned con that provides an opportunity for true feelings to develop.
Boys and Girls
Jennifer (Claire Forlani) and Ryan (Freddie Prinze Nr.) are UC Berkeley undergraduates who have known each other since their early youth.
He’s a methodical, literal, and serious engineering student who always works on a plan; she’s fast, funny, sarcastic, literary, and fiercely independent.
While consoling one another over their respective romantic tribulations, they spend a night together that is followed by a whirlwind of emotional chaos.
As Jennifer’s graduation trip to Italy inches closer, audiences are left wondering whether these polar opposites will find common ground.
If the love-hate relationship between Kat and Patrick piqued your interest, you would enjoy the playful dynamic between Jennifer and Ryan.
A Walk to Remember
When a prank goes awry and lands a student in the hospital, Carter (Shane West), a popular kid with no aspirations for the future, is dealt his punishment; plenty of painful hours of after-school community service.
This is where Carter meets Jamie Sullivan (Mandy Moore), a sweet but self-assured high school dork.
When Landon decides to take his activities more seriously, he seeks Jamie’s assistance. As they spend more time together, Carter begins to see past Jamie’s geeky façade.
Despite the dissatisfaction of Carter’s friends and Jamie’s protective father, the two begin to date. However, when Jamie reveals a devastating secret, their love story takes a turn for the worst.
Both 10 Things I Hate About You and A Walk to Remember have plotlines centered around unlikely matches. The playful dynamic between Carter and Jamie is comparable to the relationship between Kat and Patrick.
Can’t Buy Me Love
After inadvertently destroying her mother’s designer wardrobe, geeky Ronald Miller (Patrick Dempsey) saves queen bee Cindy Mancini (Amanda Peterson) from punishment. Ronald offers to pay for the damaged clothes on the condition that Cindy pretends to be in love with him for a month.
As Ronald gains popularity and these two polar opposites spend more time together as a fake couple, they begin to develop real feelings for one another. However, when Ronald quickly discovers that social status isn’t everything when his newfound reputation gets to his head.
This classic teen rom-com centers around a high school hierarchy and a carefully planned scheme to climb it. Like 10 Things I Hate About You, this film exemplifies how opposites attract, and that true connection is priceless.
Whatever It Takes
Ryan (Shane West) is a nerdy high schooler who only has eyes for Ashley (Jodi Lyn O’Keefe), the school’s bombshell. His best friend and neighbor, Maggie (Marla Sokoloff), disapproves of his crush.
When the alpha jock, Chris (James Franco), sets his sights on Maggie, he strikes a deal with Ryan to land them their dream girls.
However, their contradistinctive personalities initially throw a wrench in the works. But as they begin to win over their women, Ryan begins to see Maggie in a new light and wonders if he’s pursuing the right girl.
Both 10 Things I Hate About You and Whatever It Takes create dramatic irony through a carefully calculated scheme that brings two unlikely sweethearts together.
Pretty in Pink
Pretty in Pink follows the less-than-perfect life of Andie (Molly Ringwald), a high school outcast from an underprivileged neighborhood in Chicago. She spends most of her time with her buddies Iona (Annie Potts) and Duckie (Jon Cryer), who has always had a crush on her.
Andie catches the eye of Blane (Andrew McCarthy), a wealthy and popular new student. However, Andie soon realizes that she does not belong in Blaine’s cruel, elitist world. They are driven apart by their class but later discover that true love conquers all.
If you enjoyed the labyrinth of high school drama in 10 Things I Hate About You, you will fall in love with this classic teen rom-com.
The Breakfast Club
Claire Standish (Molly Ringwald), Andrew Clark (Emilio Estevez), John Bender (Judd Nelson), Brian Johnson (Anthony Michael Hall), and Allison Reynolds (Ally Sheedy) have nothing in common outside of being in the same class at Shermer High School.
Claire is a queen bee, Andrew is a jock, John is a delinquent, Brian is an academic, and Allison is an oddball, to put it simply.
However, they are bound by one thing; they have a nine-hour detention in the school library on Saturday. Their punishment is an essay about who they think they are.
These five students embark on a journey of self-reflection and begin to realize that they are not as different as they initially believed themselves to be.
10 Things I Hate About You and The Breakfast Club explore the theme of how we are bound by the stereotypes with which we align and how freeing ourselves from these restrictions allows us to find a true connection.
Lloyd (John Cusack) is a perpetual optimist whose goal is to win the heart of the beautiful Diane Court (Ione Skye), their graduating class’s valedictorian. Lloyd musters the courage to ask Diane to be his date to their graduation party, and to his surprise, she agrees.
As they spend time together, they begin to develop a deeper connection.
However, these unlikely sweethearts face several obstacles that tear them apart right before Diane is supposed to leave for a prestigious fellowship in Britain. Despite these challenges, love conquers all in this classic teen rom-com.
Like 10 Things I Hate About You, Say Anything is a typical teen romantic comedy riddled with high school hierarchies and agonizing heartbreaks.