The 10 Things I Hate About You zealots can be split into two categories: English majors and people who believe in love. These are two distinctly different categories of human. And to be clear, 10 Things I Hate About You, a modern retelling of The Taming of the Shrew, is considered one of the best modern Shakespeare adaptations, joining a hoard of other films that bring Shakespeare’s works into the modern form.
Whether you’re looking for brain food or soul food (or both), here are the best movies to binge after rewatching 10 Things I Hate About You.
For Shakespeare Stans
Romeo + Juliet
Cinema history lite and a bit of mainstream camp, the 1996 adaptation Romeo + Juliet stars Leonardo DiCaprio and Claire Danes as, well, you know who. An early work from maximalist filmmaker Baz Luhrmann, the hand behind Elvis and Moulin Rouge!, the film reimagines the iconic Shakespeare epic in Verona (read Venice) Beach. A tough watch for half-listeners, the film’s script remains faithful to the original text, iambic pentameter and all, despite the modernization of setting, props, and costuming.
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Deliver Us From Eva
Starring Gabrielle Union and LL Cool J, Deliver Us From Eva, like 10 Things I Hate About You, is a modern adaptation of Shakespeare’s The Taming of the Shrew. In this rom-com, a man is paid to date a “difficult” woman. “Difficult” in this sense—most senses when used to describe a woman—means career focused, indifferent towards the whims of men, and protective of the women in her life. The “shrew” trope is a common one, can we blame that one on Shakespeare himself?
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Hamlet
The 2000 adaptation of this iconic tale is set in modern day New York City and stars Ethan Hawke (naturally) as a film bro. Like Luhrmann’s Romeo + Juliet, Hamlet shares its dialogue with the original epic, but features modern technology like security cameras and surveillance tech. This adaptation moves away from royalty in the literal sense, rather focusing on corporate loyalty, a la Succession. Kyle MacLachlan also stars in the film, standing as the head of a major corporation, rising to power by killing his brother, Hamlet’s father.
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My Own Private Idaho
This 1991 adaptation comes from master auteur Gus Van Sant, the mind behind such works as Milk, Good Will Hunting, and Elephant. My Own Private Idaho, an adaptation of Shakespeare’s Henry plays, stars River Phoenix and Keanu Reeves as two friends on a journey to find one’s mother. Phoenix plays a prostitute suffering from narcolepsy, regularly losing consciousness and waking up in mysterious places. The film remains a cult classic, especially beloved in the LGBTQ+ community.
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She’s The Man
Perhaps Amanda Bynes’ most iconic role? She’s The Man on its face is a teen rom-com, but if you dig a little deeper, you’ll find a pretty clever adaptation of Shakespeare’s Twelfth Night. Bynes’ plays a teenage soccer player attending a new boarding school with no women’s soccer team, forcing her to join the team in highly believable boy drag.
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Much Ado About Nothing
Slay cast alert! The 1993 adaptation of Shakespeare’s Much Ado About Nothing stars Kenneth Branagh (who also wrote and directed the film) alongside Emma Thompson, Michael Keaton, Denzel Washington, Kate Beckinsale, and Keanu Reeves. Relatively faithful to the original text, the film follows two young lovers who try to play matchmaker with two comical enemies. It’s the original “will they, won’t they?” and spoiler alert, they all do.
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The Tragedy of Macbeth
The newest Shakespeare adaptation on the market, The Tragedy of Macbeth stars Denzel Washington and Frances McDormand and comes from A24. It’s Shakespeare for the indie kids. Of all the adaptations on this list, this one is probably the least comical, the most thrilling, and absolutely the least saturated (it’s a black and white film, you see).
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The King
This Netflix drama, an adaptation of Shakespeare’s Henry series, stars Timmy Chalamet, Joel Edgerton, Lily-Rose Depp, and Robert Pattinson. Less of an artistic adaptation and more of a historical retelling, the film follows the rise of the young King Henry V after the death of his father. If you ask the historians (or your English professors), The King is far from faithful to both the history and the literature, but hey, it’s fun.
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For Young Lovers
Clueless
So you didn’t come here for SparkNotes, got it. If the thing you love about 10 Things I Hate About You is the teenage romance, look no further and read on. This 1995 classic is the pivotal coming-of-age film for millennial women. It may not be Shakespearean in nature, but Clueless is actually a loose adaptation of a Jane Austen novel from 1815, Emma. Set in modern-day Beverly Hills, Clueless follows a group of wealthy popular high schoolers who perform a makeover on a new student to raise her status, but even that is oversimplifying the magic of this movie. Just watch it, as if you haven’t already.
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Never Been Kissed
This 1999 rom-com stars Drew Barrymore as a successful journalist in her mid-twenties who has never been in a relationship. True to the genre of 2000s journalism comedies, Barrymore’s character is given an asinine assignment, to go undercover at a high school and report on the lives of real teenagers. Along this journey, she is forced to reckon with her own experience of adolescence, once marked by the kind of geekdom that creates great journalists.
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Easy A
Emma Stone, if you’re reading this, we love you. This 2010 comedy stands as another great literary adaptation, this time of Nathaniel Hawthorne’s The Scarlet Letter. Stone plays a teenager who, after building a false reputation as, shall we say, a harlot, decides to take her self-image into her own hands. Depending on who you ask, this is commercial feminist history, and for 2010, was pretty damn empowering.
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Cruel Intentions
A bona fide cult classic, Cruel Intentions stars Sarah Michelle Gellar, Reese Witherspoon, and Ryan Phillippe. The film is adapted from the 1782 novel Les Liaisons Dangereuses, but is set in a Gossip Girl world, among the rich teens of New York City.
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Love, Simon
A high school love story for the social media age, Love, Simon stars Nick Robinson as the eponymous Simon, a closeted gay teenager facing a threat of being outed by a blackmailer, while also becoming infatuated with an anonymous secret admirer.
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Lady Bird
Let’s call Lady Bird what it is, the greatest coming-of-age film of the last decade. From writer-director Greta Gerwig, the film stars Saoirse Ronan as an angsty, ambitious, aspirational teenager stuck in the uninspired suburbs of Sacramento. The film focuses on her search for identity and her relationship struggles, mainly with her mother. In its awards year, Gerwig stood as the sole female Best Director nominee, inspiring the iconic Emma Stone quip, “this year’s nominees, four men and Greta Gerwig.”
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Say Anything
The vintage representation on this list, Say Anything stars John Cusack as a slacker student who falls in love with the class valedictorian after graduating from high school. A classic story of the guy trying to get the girl, Say Anything is considered one of the greatest romance movies ever made, topping the list of the best high school movies ever made.
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Courtney Young is a freelance writer covering all things entertainment and pop culture, having previously written for Betches, Mic, and The Cut. Her Real Housewives locale of choice is New Jersey, her emotional support show is Girls, and her toxic trait is romanticizing mafia culture. You can follow her on Instagram @courtneyyoungg.
