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It’s been 23 years since 10 Things I Hate About You released and fans still can’t get enough. Starring Julia Stiles and Heath Ledger, this film is one of the quintessential rom-coms still on the top of everyone’s favorites list. 10 Things is a story about two sisters, Kat (Stiles) and Bianca (Larisa Oleynik) who couldn’t be more different. Kat, uninterested in the male gaze and focused on her future, becomes wooed by Patrick (Ledger) who is paid to date her so that Bianca is allowed to date per their father’s rules. Kat and Patrick couldn’t be more opposite than they are, yet it works. There’s a grand display of love via a bleacher solo performance, a tear-jerker of a love confession poem, and plenty of ’90s feel-good vibes to love.
While we could watch this over and over again, sometimes it’s best to branch out. Here are some of the best films to watch if 10 Things I Hate About You is one of your favorites.
A Knight’s Tale
If you need another Heath Ledger dance performance, A Knight’s Tale has what you are looking for. In this medieval era comedy, Ledger stars as William Thatcher, who enters jousting tournaments under the guise that he is a nobleman and not a peasant. But, of course, he meets high society Jocelyn (Shannyn Sossamon) and begins to fall in love. The question remains, will Jocelyn still love him when she learns who he really is? The late Ledger provides so much charm and proves, yet again, that he is great in the role of a romantic lead.
She’s All That
’90s heartthrob Freddie Prinze Jr. stars as Zack Siler, the popular jock in his school. His picture-perfect relationship with popular girl Taylor ends when she publicly dumps him for someone else. Determined to get his swagger back, he is bet that he can’t turn the nerdy girl into a prom queen. Classic ’90s romantic comedy move. The nerdy girl is Laney Boggs (Rachael Leigh Cook) and he does in fact transform her, but he also falls in love with her. Following a similar pattern as 10 Things with the bet, She’s All That has an all star cast (Matthew Lillard, Paul Walker) and a story of opposites attracting that you can’t help but get invested in.
Clueless
Possibly one of the most quotable ’90s romantic comedies is Clueless. This film follows popular girl Cher (Alicia Silverstone) as she navigates high school and its trials and tribulations. She plays matchmaker, makeover artist, fashionista, and the voice of reason for a lot of her friends, but seemingly can’t find love herself. When will it be Cher’s turn? In another display of opposites attract, viewers watching this movie will see long before the lead characters do that they’re in love with each other. This film hits on all the nostalgia points of high school in the ’90s and early 2000s, and it’s cast, starring Paul Rudd, Brittany Murphy, and Stacey Dash, is impeccable.
Never Been Kissed
This film doesn’t feature a dating bet, but we do get some amazing makeover transformations, deception, and high school nostalgia. Drew Barrymore is Josie Geller, a news journalist posing as a high school student to get the inside scoop for an article she wants to write. Being the unpopular girl when she was in high school, Josie jumps at the chance to get redemption and become a popular girl. The only hiccup? Pretending to be a high school student and falling for your English teacher isn’t exactly acceptable. Watch Josie transform and grow in self-confidence through the course of this movie that will have you laugh, swoon, and maybe even tear up a little bit. Plus, the fashion and soundtrack is essential ’90s.
Drive Me Crazy
Melissa Joan Hart and Adrian Grenier star as Nicole and Chase in this often overlooked rom-com about two childhood friends who use each other to make their crushes and exes jealous. As Nicole and Chase spend more time together and get closer, what was initial hatred and bickering turns into soft romance and slowly falling for each other. This film is another one with a killer soundtrack, the name of the film deriving inspiration from Britney Spears‘ “Drive Me Crazy.” With the late ’90s and early 2000s being inundated with romance comedy movies, this one often gets left out of the lists where it does deserve a spot.
Easy A
One of the more recent films on this list, Easy A takes inspiration from the book The Scarlet Letter as Olive (Emma Stone) lies about losing her virginity. The lie continues to spiral into outrageous rumors that Olive decides to proudly wear an “A” and pretend to be a bad girl as well. Olive starts to get closer to her crush, Todd (Penn Badgley) and now has to find a way to get rid of the bad reputation and get the good reputation she had back. This was the breakout role for Emma Stone, and it is hilariously clever from start to finish.
Cruel Intentions
Another film where the popular kids use the nerds and goody two-shoes as pawns in their game, Cruel Intentions explores entitlement, sexual conquest, and an unlikely change in character from a few of the ones who don’t seem to be redeemable. Sebastian (Ryan Phillippe) takes a bet from step-sister Kathryn (Sarah Michelle Gellar) that he can get Annette (Reese Witherspoon) to break her abstinence pledge for him. Sebastian’s aim is to make Annette fall in love with him, but he absolutely gets more than he bargained for by the end of the film. This one is a classic and the performances from the cast are so on point that you can’t help but get angry, happy, and sad for each character.
The Proposal
Sandra Bullock is fantastic and in The Proposal she plays the role of Margaret Tate, a successful book editor whose work visa has expired, and she is faced with deportation. In order to avoid losing her clients or potentially her job, Margaret convinces her assistant, Andrew (Ryan Reynolds), to marry her so he and she can both keep their jobs. The unlikely pair who can’t stand each other explore Alaska, Andrew’s home state, together trying to navigate how to get away with the wedding without the lie being revealed. Including some excellent performances from the late Betty White and Mary Steenburgen, this film will give you the warm fuzzies and make you belly laugh from start to finish.
She’s The Man
Viola (Amanda Bynes) is a talented soccer player who pretends to be her brother, Sebastian, in order to play on an all-boys team. There’s just one hiccup; she starts to fall in love with her roommate, Duke (Channing Tatum), who believes she is a guy. To make matters worse, Duke wants Viola to set him up with a girl who is in love with Viola as Sebastian! Based off of the Shakespeare play, Twelfth Night, She’s The Man is hilarious from start to finish and filled with so much on-screen chemistry between Bynes and Tatum.
Can’t Hardly Wait
This film provides the same nostalgia of teenage hangouts as 10 Things does, centering the plot around an end of the year party where Preston (Ethan Embry) only has one more chance to tell Amanda (Jennifer Love Hewitt) that he has a crush on her. Preston and all of his friends are trying to end the year on a high note, and this movie follows closely each of their decisions and actions in the most relatable way possible. From start to finish, you’ll re-experience the highs and lows of high school with the cast and moments that will have you laughing and swooning all at the same time.
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