Cameron James, a new student at Padua High School in the Seattle area, becomes instantly smitten with popular sophomore Bianca Stratford. Geeky Michael Eckman warns him that Bianca is vapid and conceited, and that her overprotective father does not allow Bianca or her older sister, the shrewish Kat, to date. Kat, a senior, is accepted to Sarah Lawrence College in New York, but her father, Walter, wants her to stay close to home. Bianca wishes to date affluent senior Joey Donner, but Walter, an obstetrician worrisome of teenage pregnancy, will not allow his daughters to date until they graduate. Frustrated by Bianca's insistence and Kat's rebelliousness, Walter declares that Bianca may date only when Kat does, knowing that Kat's antisocial attitude makes this unlikely.
When Cameron asks Bianca out, she informs him of her father's new rule and, as a pretense for allowing her to date Joey, suggests that Cameron find someone willing to date Kat. Cameron selects "bad boy" Patrick Verona, but Patrick scares him off. Michael assists by convincing Joey to pay Patrick to take out Kat, under the pretense that this will allow Joey to date Bianca. Patrick agrees to the deal, but Kat rebuffs his first few advances. Michael and Cameron help him by prying Bianca for information on Kat's likes and dislikes. Armed with this knowledge, Patrick begins to win Kat's interest. She goes to a party with him, which enables Bianca to go as well, much to Walter's dismay.
At the party, Kat becomes upset when she sees Bianca with Joey, and responds by getting drunk. Patrick attends to her, and Kat starts to open up, expressing her interest in starting a band. However, when she tries to kiss him, Patrick pulls away and Kat leaves, infuriated. Meanwhile, Bianca ignores Cameron in favor of Joey, leaving Cameron dejected. Bianca soon realizes, however, that Joey is shallow and self-absorbed, and asks Cameron for a ride home. Cameron admits his feelings for her and his frustration with how she has treated him. Bianca responds by kissing him.
Joey offers to pay Patrick to take Kat to the prom so he can take Bianca. Patrick initially refuses, but relents when Joey offers him more money. Kat is still angry with Patrick, but he wins her over by serenading her with the accompaniment of the marching band, and she helps him sneak out of detention. They go on a date which turns romantic, but Kat becomes suspicious and angry when Patrick insists that she go with him to the prom, an event she is adamantly against. Bianca is irritated that Cameron hasn't asked her to the prom, and so accepts Joey's invitation, but Walter won't allow it unless Kat goes too. Kat confesses to Bianca that she dated Joey when they were freshmen and, succumbing to peer pressure, had sex with him. Afterward she regretted it and Joey dumped her, so she vowed to never again do anything just because everyone else was doing it. Bianca insists that she can make her own choices, so Kat agrees to go to the prom with Patrick, and Bianca decides to go with Cameron instead of Joey.
All is going well at the prom until Bianca learns that Joey planned to have sex with her that night. Angry that Bianca has spurned him for Cameron, Joey reveals his arrangement with Patrick, which causes Kat to leave heartbroken. Joey then punches Cameron, but is in turn beaten up by Bianca for having hurt her, Kat, and Cameron. Bianca and Cameron share another kiss.
The next day, Bianca reconciles with Kat and begins dating Cameron. Walter admits that Kat is capable of taking care of herself, and gives her permission to attend Sarah Lawrence College. For an assignment in which the students were required to write their own version of William Shakespeare's Sonnet 141, Kat reads aloud a poem titled "10 Things I Hate About You", revealing that she still loves Patrick. Patrick surprises her with a guitar bought with the money that Joey paid him, and confesses that he has fallen for her. Kat forgives him, and the two reconcile with a kiss.Julia Stiles as Katarina "Kat" Stratford, the antisocial, shrewish elder Stratford sister.
Heath Ledger as Patrick Verona, the "bad boy" who is hired to date Kat and falls for her in the process.
Joseph Gordon-Levitt as Cameron James, the new student at Padua High School who is smitten with Bianca and goes to great lengths to win her favor.
Larisa Oleynik as Bianca Stratford, the younger of the two Stratford sisters, superficial and popular.
Larry Miller as Walter Stratford, an obstetrician and single parent who is overprotective of his daughters, Kat and Bianca.
Andrew Keegan as Joey Donner, an affluent, self-absorbed high school senior and aspiring model who intends to have sex with Bianca, and to that end pays Patrick to date Kat.
David Krumholtz as Michael Eckman, a geek who assists Cameron in his quest to woo Bianca, and in the process tries to woo Kat's friend Mandella.
Susan May Pratt as Mandella, Kat's only close friend and an aficionado of William Shakespeare, who ends up going to the prom with Michael.
Gabrielle Union as Chastity Church, Bianca's best friend, who betrays Bianca by going out with Joey when Bianca spurns him.
Daryl Mitchell as Mr. Morgan, teacher of Kat, Patrick, and Joey's English class.
Allison Janney as Ms. Perky, Padua High School's guidance counselor and a writer of erotic literature.
David Leisure as Mr. Chapin, coach of the girls' soccer team.
Greg Jackson as "Scurvy", a friend of Patrick.
Kyle Cease as Bogey Lowenstein, a golf enthusiast and member of a clique of aspiring MBAs.
The band Letters to Cleo (singer Kay Hanley, guitarists Greg McKenna and Michael Eisenstein, bassist Scott Riebling, and drummer Jason Sutter) appears as the band performing at Club Skunk, playing their songs "Come On" and "Co-Pilot", and playing a cover version of Cheap Trick's "I Want You to Want Me" on the school's rooftop during the closing credits. Hanley and Eisenstein also appear in the prom scene, performing a cover of Nick Lowe's "Cruel to Be Kind" with Save Ferris.
The band Save Ferris (singer Monique Powell, guitarist Brian Mashburn, bassist Bill Uechi, trumpeter José Castellaños, trombonist Brian Williams, saxophonist Eric Zamora, and drummer Evan Kilbourne) appears as the band performing at the prom, playing their songs "I Know" and "Can't Stop" as well as covers of The Isley Brothers' "Shout" and Nick Lowe's "Cruel to Be Kind".
Many of the scenes were filmed on location at Stadium High School and at a house in the Proctor District of Tacoma, Washington. The prom sequence was shot over three days in Seattle.
Costume designer Kim Tillman designed original dresses for Larisa Oleynik and Julia Stiles as well as the period outfits for Susan May Pratt and David Krumholtz. Gabrielle Union's snakeskin prom dress is a Betsey Johnson design. Heath Ledger and Joseph Gordon-Levitt's vintage tuxes came from Isadora's in Seattle.
The primary tagline is an allusion to a poem written by Elizabeth Barrett Browning from her Sonnets from the Portuguese collection. ("How do I loathe thee? Let me count the ways.") Another tagline is a spoof from Shakespeare's Romeo and Juliet ("Romeo, Oh Romeo, Get Out Of My Face.") and another is a line from The Taming of the Shrew that is spoken in the film by Cameron ("I burn, I pine, I perish!"). The original script was finalized on November 12, 1997.
In its opening weekend, the film grossed US$8,330,681 in 2,271 theaters in the United States and Canada, averaging $3,668 per venue, and ranking number two at the box office (behind The Matrix). It grossed a total of $38,178,166 in the United States and Canada and $15,300,000 in other territories, about $53,500,000 worldwide. The film had an estimated budget of $16 million and is considered a moderate financial and critical success. On October 12, 1999, the Region 1 DVD was released. In the box office, the film is number ten in teen romance, 18th in high school comedies, and ranked 96th in comedies.
The film received generally positive feedback from critics. Geoff Andrew from Time Out praised the film's leads, stating "Stiles grows into her character, and Ledger is effortlessly charming". Roger Ebert gave the film two and a half stars out of four, claiming "I liked the movie's spirit, the actors and some of the scenes. The music, much of it by the band Letters to Cleo, is subtle and inventive while still cheerful". Brad Laidman from Film Threat said the film was "Pure of heart and perfectly executed". Ron Wells, another critic from Film Threat expressed "Of all the teen films released this year, this one is, by far, the best".
Entertainment Weekly listed the film at #49 on its list of Best High School Movies.
On Rotten Tomatoes, the film got a 61% from critics, based on 62 reviews with a rating of 6.1/10. The critical consensus on the site was "Julia Stiles and Heath Ledger add strong performances to an unexpectedly clever script, elevating 10 Things (slightly) above typical teen fare."
10 Things I Hate About You was a breakout success for stars Stiles, Ledger and Gordon-Levitt. Gordon-Levitt, Stiles, and Oleynik each received Young Star Award nominations for Best Actor/Actress in a Comedy Film. The movie was nominated for seven Teen Choice Awards: Choice Movie: Breakout Star (Stiles), Choice Movie: Comedy, Choice Movie: Funniest Scene (featuring Krumholtz), Choice Movie: Love Scene (featuring Stiles and Ledger), Choice Movie: Hissy Fit (Gordon-Levitt), Choice Movie: Villain (Gordon-Levitt) and Choice Movie: Soundtrack. The film's casting directors Marcia Ross and Donna Morong won "Best Casting for Feature Film, Comedy" at the Casting Society of America in 1999. In 2000, Stiles won the CFCA Award for "Most Promising Actress" for her role as Kat Stratford (tied with Émilie Dequenne in Rosetta) and an MTV Movie Award for Breakthrough Female Performance. The same year, Ledger was nominated for Best Musical Performance for the song "Can't Take My Eyes Off You".
In June 1999, the Scholastic Corporation published a novelization of the story, adapted by David Levithan. The story is retold as it is in the film with each chapter written from the point of view of either Bianca, Cameron, Kat, Patrick, or Michael.
In October 2008, ABC Family ordered a pilot episode of 10 Things I Hate About You, a half-hour, single-camera comedy series based on the feature film of the same name. Larry Miller is the only actor from the film to reprise his role in the television series. The director of the film, Gil Junger, directed many of the episodes including the pilot while the film's music composer, Richard Gibbs, also returned to do the show's music. The series was adapted and produced by Carter Covington. The show premiered on July 7, 2009, and lasted 20 episodes.