Maybe you fell head over heels for 10 Things I Hate About You the moment Julia Stiles’ Kat Stratford danced to Biggie on a tabletop and fell into the arms of Heath Ledger’s Patrick Verona, or maybe it was his grand football field serenade. Countless moments in the teen romantic comedy make it special, and one of the most iconic ‘90s movies.
Since its 1999 debut, this contemporary adaptation of William Shakespeare’s The Taming of the Shrew about the dating dilemma of the teenage Stratford sisters (played by Stiles and Larisa Oleynik) has become a rewatchable favorite. It arrived amid a heyday of teen blockbusters, and also—with its memorable soundtrack and thoughtful grip on how challenging it can be to be a young person navigating identity and romance—went on to influence teen movies that followed.
If you’ve seen 10 Things I Hate About You dozens of times over the years, or just got around to seeing it for the first time, and are looking for a similar movie to watch next, there are many great options within the same coming-of-age lane. From similar ‘90s flicks to beloved 2000s movies to even other modernized versions of classic literature and underrated cult classics you may have missed, here’s what you should watch if you love 10 Things I Hate About You.
'A Knight's Tale' (2001)
If Y2K Heath Ledger is where your heart’s at, queue up A Knight’s Tale. His character William Thatcher in this medieval-era action-comedy could beat Patrick Verona in a duel of the most charming. When William’s master dies, he puts his peasantry behind him and poses as a knight to win jousting tournaments and the heart of the lady he’s pining for (Shannyn Sossamon). Ledger may have gone on to take on more dramatic, even darker roles, but this one remains an adorable, underrated gem.
'Booksmart' (2019)
Not every teen comedy can be a generation-defining, instant classic like 10 Things About You, but Booksmart surely is. This Olivia Wilde-directed film has all the makings of a great teen movie—from incredible needle drops to a memorable wardrobe—and laugh-out-loud funny jokes that fly one after another through the movie’s quick-witted, snappy pace. It all goes down as a night of hilarity ensues when best friends Amy (Kaitlyn Dever) and Molly (Beanie Feldstein) decide to get all their high school partying out in one night when they realize they may have gone overboard only spending the last four years hitting the books.
'Can’t Hardly Wait' (1998)
Can’t Hardly Wait doesn’t always get as much love as other ‘90s teen movies, but it’ll still take you to “Paradise City.” Various will-they-won’t-they relationships and a whole lot of hijinks ensue during one graduation party. The ensemble is filled out by a handful of stars from the era, from Jennifer Love Hewitt to Ethan Embry, and includes blink-and-you’ll-miss-it cameos from names like Selma Blair, Jason Segel, Clea DuVall, and others as they were on the cusp of breaking out.
'Clueless' (1995)
“As if” we need to tell you to watch Clueless? Like 10 Things I Hate About You, this iconic ‘90s movie reimagines a classic piece of literature. A modern retelling of Jane Austen’s Emma, Alicia Silverstone’s Cher is the stand-in for the silly, meddling Emma and the Valley is the contemporary take on Regency-era England. Whether you’re looking for fashion inspiration or to see how many quotes you can still cite by heart, Clueless is always worth a rewatch.
'Cruel Intentions' (1999)
Albeit darker than 10 Things I Hate About You, Cruel Intentions, too, takes its source material from a centuries-old work. Here, Dangerous Liaisons unfolds in the elite world of Manhattanite teenagers who grew up on the Upper East Side and spend their summers in the Hamptons. The teenage schemes are a bit nastier than the Stratford sisters’ plan to find a workaround for their inability to date—as conniving queen bee Kathryn (Sarah Michelle Gellar) convinces her playboy stepbrother Sebastian (Ryan Phillippe) to seduce good girl Annette (Reese Witherspoon) as a bet—but it’s a delicious teen drama that many felt a hint of rebellion watching at sleepovers.
'Dazed and Confused' (1993)
Alright, alright, alright: There are many reasons Dazed and Confused is a legendary ‘90s cult classic. Just as 10 Things I Hate About You captures the emotional intensity and the social pressures of high school, this slice-of-life Richard Linklater comedy captures how lackadaisical it can feel. Set on the last day of school in Austin, Texas in 1976, it follows various characters as a class of rising seniors haze in the upcoming freshman class. Many faces of the ensemble would go on to become stars (Ben Affleck, Milla Jovovich, Matthew McConaughey, Parker Posey) and it’s got one of the best soundtracks of all time.
'Deliver Us From Eva' (2003)
You can see the same plot as 10 Things I Hate About You unfold in Deliver Us From Eva. Also based on The Taming of the Shrew, the rom-com finds Gabrielle Union (who just so happens to appear in 10 Things I Hate About You) as the equivalent of Stiles’ Kat but a Type A inspector in the Los Angeles Health Department. Because her meddling, perfectionist nature has gotten in the way of her sisters’ and their partners’ romantic lives, they put their old friend Ray (LL Cool J) up to wooing her.
'Drive Me Crazy' (1999)
Did the enemies-to-lovers cliche of 10 Things I Hate About You warm your heart? Drive Me Crazy copies from the same textbook, and to sweet results. Sabrina the Teenage Witch herself Melissa Joan Hart stars as a status-obsessed high school senior who asks her former friend and neighbor, the moody, artistic Chase (Adrian Grenier), to pretend to be her boyfriend to make their respective exes jealous. The plot writes itself, but it’s oh so very ‘90s and not every movie gets its name from a killer needle drop of Britney Spears’ "(You Drive Me) Crazy.”
'Drop Dead Gorgeous' (1999)
There were a lot of hit teen movies in the ‘90s and a lot of overlooked gems. If you’re looking for a recommendation from the era you may not have seen, but is sure to become a new favorite, tune into Drop Dead Gorgeous. A handful of then-emerging stars make up the ensemble (Kirsten Dunst, Brittany Murphy, Denise Richards, Amy Adams), along with comic legends (Allison Janney, Kirstie Alley), in his absurdist mockumentary about a teen beauty pageant in rural Minnesota that soon turns dark when one by one the contestants get killed off.
'Easy A' (2010)
Easy A toys with beloved teen movie sensibilities and the concept of playing with famous literature to create an original, genuinely funny 2010s entry into the high school comedy canon. Inspired by her class’ assignment to read Nathaniel Hawthorne’s The Scarlet Letter, 17-year-old Olive (Emma Stone) spews a rumor mill of her own by lying about losing her virginity and letting socially awkward boys say they hooked up with her in exchange for payment. Witty, with smart messaging about sex and social conventions, and held down by a star-making performance from Stone, Easy A is a “Pocket Full of Sunshine” of a movie.
'The Edge of Seventeen' (2016)
For a more contemporary coming-of-age recommendation, The Edge of Seventeen will surely pull on your heartstrings and remind you of all the angst you felt back in the day. High school junior Nadine (Hailee Steinfeld) is just as cynical as Kat, although wildly more dramatic—which is an attitude that leads her to act out when she discovers her best friend (Haley Lu Richardson) is dating her brother (Blake Jenner). Steinfeld will make you and all of your anxieties, from teenhood and on, feel seen, and you’ll wish you could’ve had Woody Harrelson as your teacher.
'Empire Records' (1995)
10 Things I Hate About You has an excellent soundtrack—and multiple Letters to Cleo cameos to support it. Empire Records is another ‘90s flick that has the pulse on just how much music can mean to young people. It’s essentially the dream of Gen X embodied into a teen comedy, as it’s set over one day when a team of record store employees band together to try to stop their shop from being sold to a chain. You can bet Kat would’ve joined in the protest (and listening to The Cranberries) along with them.
'Fast Times at Ridgemont High' (1982)
While 10 Things I Hate About You feels defining of the late ‘90s moment it came out in, Fast Times at Ridgemont High reflects on teendom in the ‘80s. Set in the Valley, it chronicles a year in the life of a group of high schoolers as they dabble in partying, sex, and emotional turmoil while their adolescence seemingly flies by. Raunchy but still ahead of its time, the film was written by Cameron Crowe and marked the feature directorial debut of Amy Heckerling, who went on to write and direct Clueless.
'Ghost World' (2001)
If you felt connected with Kat’s wallflower disposition, then Ghost World is for you. This weird girl cult classic is based on Daniel Clowes’ graphic novel of the same name and follows outcasts Rebecca (Scarlett Johansson) and Enid (Thora Birch) as they answer a personal ad for a man named Seymour (Steve Buscemi) to prank him, and end up intervening in his love life. The characters are all loveable oddballs who know just how tough adolescence, and life in general, can get—just like Kat.
'Never Been Kissed' (1999)
Despite its dated flaws that wouldn’t fly in a more contemporary movie, Never Been Kissed holds a special place in many ‘90s and ‘00s kids’ hearts—largely because of how adorable its star Drew Barrymore is. The film, released in 1999 amid the teen craze at the box office that year alongside 10 Things I Hate About You, sees Barrymore as Josie, a 25-year-old journalist who goes undercover as a high schooler to investigate what the kids these days are into. Having been bullied herself back in the day and (as the title suggests) having never been kissed, she gets a second shot at growing up.
'Pretty in Pink' (1986)
If you’re more of a Bianca than a Kat, Pretty in Pink may be for you. This iconic John Hughes movie features ‘80s it girl Molly Ringwald as Andie, a high schooler from a low-income family who’s self-conscious about her class but has a penchant for fashion and close friendship with fellow outcast Duckie (Jon Cryer). Despite their “richie” classmates’ snide remarks, she falls for nice guy prep Blane (Andrew McCarthy), and a relatable story about facing insecurities and embracing big feelings plays out. (Just don’t get us started on how they changed the original, which would have made for an even more heartwarming movie.)
'Save the Last Dance' (2001)
Julia Stiles gives her best on-screen dance performance in 10 Things I Hate About You, but Save the Last Dance is her starring turn in a dance movie. In truth, it’s much more of a romance set against the backdrop of dance. When tragedy strikes, Stiles’ aspiring ballerina character Sara moves in with her estranged father on the Southside of Chicago, where she attends a high school with mostly Black students and finds herself immersed in a new nightlife scene. There, she meets Derek (Sean Patrick Thomas), who she falls for as he helps her prepare for a Juilliard audition. Her “big audition” scene has since become highly memed—and wouldn’t have gotten her into the school in real life—but at least we have Stiles’ charisma to carry this teen drama.
'She’s All That' (1999)
The ‘90s really had a thing for modern adaptations of beloved stories. She’s All That is a high school take on the George Bernard Shaw play Pygmalion, in which cool kid Zack (Freddie Prinze Jr.) agrees to a bet that he can turn any girl on campus into prom queen in six weeks. When his friend (Matthew Lillard) chooses the quiet, artistic Laney (Rachel Leigh Cook), he feels he’s in for a challenge, until she ultimately charms him. It may not be a total stand-out in the pantheon of teen movies, have questionable messaging about beauty, and fall ill to the takes off her glasses trope, but the leads’ chemistry makes it a sweet, little flick.
'She’s the Man' (2006)
She’s the Man modernizes Shakespeare’s Twelfth Night. In a wild ruse, when the girls’ soccer team is cut at Viola’s (Amanda Bynes) high school and she’s unable to try out for the boys’ team, she goes undercover as her twin brother at his boarding school to make a point. Of course, a comedy of errors ensues. Centered around Bynes’ incredible transformative performance and brand of physical comedy, this is a seriously funny movie we’re still quoting today—and in the exact cadence of speech as Bynes.
'To All the Boys I’ve Loved Before' (2018)
It can’t be overstated what a moment it was when this adaptation of Jenny Han’s popular book series To All the Boys I’ve Loved Before came out. After years of feeling as though rom-com fans had been devoid of a great, new entry into the genre, this Netflix original offered viewers exactly what they had been searching for. Thanks to the romantic Lara Jean Covey (Lana Condor) and the suave Peter Kovinsky (Noah Centineo), whom she pretends to date when she ends up in a dilemma, our hearts were able to soar and we found a bit of faith in the teen rom-com again.
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