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How 10 Things I Hate About You Remains the Smartest High-School Comedy From 1999

A tale of a rich girl who will not date, a poor boy who seeks to change her mind, and the strange rules that govern teen romance.

By mitch·8 min read
A boy and a girl walk together along a road, their hands linked.

10 Things I Hate About You is a high school comedy about a rich girl who won’t date anyone, and the poor boy who wants to get her sister to change her mind. It is also about class, family pressure, and the strange rules that govern teenage romance in the late nineties. The film, directed by Gil Junger, takes a familiar romantic-comedy setup and turns it into a sharp, funny satire of social status and the way young people use money to settle scores.

Heather Graham plays Cameron James, a popular cheerleader who is beautiful, confident, and utterly unwilling to date anyone. Joseph Gordon-Levitt plays Patrick Du Pres, a quiet, awkward student who is desperate to impress his ex-girlfriend, Cherie. The problem is that Cameron will not date Patrick, and she will not date anyone else either. So Patrick hatches a plan: he will get Cherie to fall in love with Cameron’s sister, Kat, and then Cameron will feel jealous enough to want him back. It is a scheme built on the assumption that Kat is unlovable, which is exactly why the movie spends most of its runtime proving wrong.

Trailer, via Oscars.

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Cameron James and Her Rules

Cameron is the engine of the plot, and Heather Graham plays her with a gleeful, cartoonish cruelty that makes her scenes impossible to look away from. She tells boys to “get a life,” she sneers at Patrick’s modest car, and she rejects his advances with a disdain that feels earned rather than cruel. The film never lets us forget that Cameron has spent years being treated like a prize, and she has internalized that treatment so completely that she cannot imagine wanting anyone.

Her father, played by Larry Miller, is a controlling parent who treats his daughters as possessions rather than people. He has set up a trust fund for Cameron that she will inherit only if she marries by a certain age. This deadline drives the entire story forward, and it gives Cameron a motive beyond simple vanity: she is terrified of failing her father’s expectations. Graham plays this tension perfectly, shifting from cold disdain to genuine fear in a single scene.

The film does not excuse Cameron’s behavior. It shows her as a character with agency, making choices that hurt others, and it does not soften those choices to make her sympathetic. That honesty is part of what makes the movie work, even when it leans into its most cartoonish moments.

Kat and the Masculine World

Kat, played by Julia Stiles, is the other half of the film’s central dynamic. She is a feminist activist who is tired of being told what she should be doing with her life. She is not interested in boys, and she is not interested in following the rules that everyone else seems to accept without question. She is also deeply lonely, trapped in a family that treats her like a disappointment and a world that sees her as a freak.

The film is careful to show Kat’s intelligence and her political convictions. She is not a one-note feminist caricature; she is a person who has thought through the system she lives in and decided to resist it. When Patrick tries to get her to fall in love with Cherie, she resists at first, but then she begins to see that love might be possible after all. The movie’s final act hinges on this shift, and Stiles sells it with a performance that moves from defiance to tenderness without ever feeling forced.

The contrast between Cameron and Kat is the film’s central argument. Cameron is rewarded for being attractive and wealthy, while Kat is punished for being smart and independent. The movie is not subtle about this, but it is consistent, and that consistency is part of what makes the message land.

Patrick and His Plan

Patrick is the film’s moral center, and Joseph Gordon-Levitt plays him with a quiet desperation that makes his schemes feel both absurd and sympathetic. He is not a villain, and he is not a hero. He is a boy who has been rejected and who wants to get back at the world by winning the girl he lost. His plan is elaborate, involving a fake relationship, a fabricated past, and a series of lies that unravel at the worst possible moment.

The film is generous to Patrick, showing his loneliness and his desire for connection without excusing his dishonesty. He knows what he is doing is wrong, but he convinces himself that the ends justify the means. That tension is the heart of the movie’s middle section, and it keeps the audience invested even when the plot grows increasingly complicated.

Gordon-Levitt carries the film’s emotional weight, and he does it without ever becoming too serious. His performance is warm and sincere, and it grounds the movie’s satirical edge in something real.

The Supporting Cast

The supporting cast is strong across the board, and the film gives each actor room to breathe. Larry Miller plays Cameron’s father with a mix of menace and desperation that makes him terrifying and pathetic in equal measure. Marisa Tomei plays Pauline, the girls’ mother, who is trapped in a marriage to a man she clearly despises. She is a standout performance, delivering some of the film’s funniest lines with a weary, resigned humor.

The film also features a group of supporting characters who populate the school’s social hierarchy. There is the popular clique, the jocks, the nerds, and the outcasts. Each group gets a brief sketch, and the film uses these sketches to comment on the way teenagers organize themselves around power and status.

The film’s satire is broad, but it is also pointed. It does not just mock the social hierarchy; it shows how that hierarchy hurts people. The popular kids are shown as shallow and cruel, but the film also shows that they are trapped by their own success. They have everything, and yet they are unhappy.

The Romance Between Kat and Patrick

The film’s central romance is the one that matters most. Kat and Patrick are opposites in almost every way, and yet they find common ground in their shared outsider status. Kat sees Patrick as a kindred spirit, someone who understands what it is like to be judged for who you are. Patrick sees Kat as someone who is not afraid of him, someone who respects him for who he is.

Their scenes together are the best in the film, and they are the reason the movie’s ending works. The romance is not just a plot device; it is the emotional core of the story. The film builds to a climax where Kat and Patrick finally admit their feelings, and the moment lands because the audience has spent the entire movie watching them circle each other.

The film’s ending is a happy one, but it is not a fairy-tale ending. Kat and Patrick do not live happily ever after in some abstract sense. They live happily ever after because they have found each other, and because they have both changed. Kat has learned to let love in, and Patrick has learned to stop lying. The film’s final image is of the two of them walking off together, and it feels earned.

The Film’s Weak Points

The film is not perfect. Its satire can be heavy-handed, and its jokes sometimes land with a thud rather than a laugh. Some of the secondary characters are thin, reduced to types rather than individuals. And the plot, while clever, can feel convoluted in its later stretches, with twists that strain credibility.

But these weaknesses are outweighed by the strengths. The performances are excellent, the writing is sharp, and the film’s central argument about class and gender is delivered with clarity and conviction. It is a movie that knows exactly what it wants to say, and it says it with confidence.

The film’s flaws are real, but they are minor compared to what it achieves. It is a movie about teenage rebellion that never loses sight of the stakes, and it is a comedy that never stops being funny.

A Comedy With Something to Say

10 Things I Hate About You is a comedy, but it is also a critique of the social structures that govern teenage life. It is a film about class, about the way wealth shapes relationships, and about the way young people are taught to value appearance over substance. It is a movie about the cost of privilege, and about the courage it takes to reject it.

The film is also a romance, and it is a very good one. Kat and Patrick are a couple who deserve each other, and their story is told with warmth and sincerity. The film’s ending is a triumph, a moment where the satire gives way to pure emotion.

It is a movie that rewards attention. It is a movie that deserves to be remembered.

10 Things I Hate About You is a flawed but essential film. It is a comedy that is smarter than most, and a romance that is warmer than expected. It is a movie about teenagers that understands what it means to be one, and it is a movie about adults that understands what it means to be young. It is a film that is worth watching again, and again, and again.

The film’s flaws are real, but they are minor compared to what it achieves. It is a movie about teenage rebellion that never loses sight of the stakes, and it is a comedy that never stops being funny.

  • Heather Graham’s Cameron is a force of nature
  • Julia Stiles gives Kat a grounded, intelligent performance
  • Joseph Gordon-Levitt anchors the film with warmth and sincerity
  • Larry Miller and Marisa Tomei deliver standout supporting work
  • The romance between Kat and Patrick is the film’s emotional center
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