10 Things I Hate About You is a 1999 American teen romantic comedy film directed by Gil Junger in his film directorial debut and starring Julia Stiles, Heath Ledger, Joseph Gordon-Levitt, Larisa Oleynik, Andrew Keegan, and Gabrielle Union. The screenplay by Karen McCullah Lutz and Kirsten Smith is a modernization of William Shakespeare's comedy The Taming of the Shrew, retold in a late-1990s American high school setting. The film follows new student Cameron James (Gordon-Levitt) who is smitten with Bianca Stratford (Oleynik) and attempts to get bad boy Patrick Verona (Ledger) to date her asocial sister Kat (Stiles) in order to get around her father's strict rules on dating. Named after a poem written by Kat about her relationship with Patrick, filming occurred in the Seattle metropolitan area, with many scenes filmed at Stadium High School in Tacoma, Washington.

Released on March 31, 1999, 10 Things I Hate About You grossed $53.7 million and received generally positive reviews from critics. It provided breakthrough roles for Stiles, Ledger, and Gordon-Levitt, all of whom were nominated for various teen-oriented awards. Ten years later, it was adapted into a television reboot, which ran for twenty episodes and featured Larry Miller reprising his role as Walter Stratford. Since its release, the film has gained popularity as a cult classic, often being cited as one of the greatest romantic comedies of all time.

Cameron James, a new student at Padua High School in the Seattle area, immediately becomes smitten with beautiful and popular sophomore Bianca Stratford. Geeky Michael Eckman warns him that she is vapid and conceited, and that her overprotective single father Walter, an obstetrician worried about teenage pregnancy, does not allow her or her shrewish older sister Kat, a senior, to date until they graduate. Kat is accepted to Sarah Lawrence College in New York, but Walter wants her to stay close to home and attend his alma mater, the University of Washington. Frustrated by Bianca's insistence and Kat's rebelliousness, Walter relents and declares that Bianca may date only when Kat does, knowing that Kat's unsocial attitude will greatly complicate it.

When Cameron asks Bianca out, she informs him of her father's new rule and suggests he find someone willing to date Kat so that Bianca can freely date affluent senior Joey Donner. Cameron selects Australian "bad boy" Patrick Verona, who initially frightens him with his attitude. Michael convinces Joey to pay Patrick to ask out Kat, to which Patrick agrees, but Kat rebuffs his first few advances. After Michael and Cameron probe Bianca for information on Kat's preferences, Patrick begins to win Kat's interest. She goes to a party with him, enabling Bianca and her best friend Chastity Church to tag along, greatly upsetting Walter.

At the party, Kat becomes upset upon seeing Bianca with Joey, and responds by getting intoxicated. Patrick attends to her, and she starts to open up to him, expressing her interest in forming a band. When Kat attempts to kiss him, Patrick pulls away, causing her to depart, infuriated. Meanwhile, Bianca upsets Cameron by ignoring him for Joey, but she soon realizes that Joey is shallow and self-absorbed. When she asks Cameron to drive her home, he admits his feelings for her are genuine and her treatment of him has frustrated him, and she reconciliatorily kisses him.

Joey offers to pay Patrick to take Kat to the prom so he can take Bianca. He initially refuses, but relents when Joey offers him more money. Although Kat is still angry with Patrick, he eventually wins her over by serenading her, accompanied by the Padua High School marching band, with a performance of "Can't Take My Eyes Off You" by Frankie Valli, and she returns the favor by assisting him in sneaking out of detention. Their subsequent date turns romantic, but Kat becomes suspicious when Patrick insists that she accompany him to the prom, which she adamantly opposes.

Irritated at not being asked to the prom by Cameron, Bianca accepts Joey's invitation, but Walter declines to allow it unless Kat accompanies her. Kat confesses to Bianca that she dated Joey when they were freshmen and, succumbing to peer pressure, had sex with him, later regretting it. After Joey dumped her, she vowed against doing anything out of peer pressure. Bianca insists that she can decide her own life, so Kat goes to the prom with Patrick, and Bianca goes to the prom with Cameron instead of Joey. Joey goes to the prom with Chastity. At the prom, Bianca learns from Chastity that Joey was planning to have sex with Bianca that night. Angry that Bianca has spurned him for Cameron, Joey reveals his arrangement with Patrick, which causes Kat to leave, heartbroken. Joey then shoves Michael and punches Cameron, but Bianca then assaults him for hurting her, Kat, and Cameron. Bianca and Cameron share another kiss.

The following day, Bianca reconciles with Kat and begins dating Cameron. Comfortable that Kat can handle herself, Walter allows her to attend Sarah Lawrence College. For an assignment in which the students were tasked to write their own versions of William Shakespeare's Sonnet 141, Kat reads aloud a poem she wrote, entitled "10 Things I Hate About You", revealing that she still loves and cares about Patrick. He surprises her with a Fender Stratocaster that he bought with the money Joey paid him, and confesses that he has fallen for her. Kat forgives him, and they reconcile with a kiss.