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This 10 Things I Hate About You trivia quiz has 80 free questions with answers and covers the 1999 film from every angle: the Stratford sisters and the boys scheming around them, Heath Ledger's bleacher serenade, the Tacoma school that played Padua High, the Shakespeare comedy underneath it all, the writers who dreamed it up after seeing Clueless, and the box office, reviews and awards that followed. It also reaches into the soundtrack, the 2009 television series and the sequels and stage musical announced since. It is built for anyone who can quote the poem scene from memory, but the early questions are gentle enough for a first-time viewer, and the later ones dig into casting near-misses and production details that reward true fans. Every answer was checked against encyclopaedia entries and other primary references before publishing, so you can argue about the results with confidence.
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Q 01Which Shakespeare comedy is 10 Things I Hate About You loosely based on?
The Taming of the Shrew
The film keeps the play's bones: a headstrong older sister, a sought-after younger one, and a suitor paid to court the difficult sibling.
Q 02Who directed 10 Things I Hate About You, in his feature film debut?
Gil Junger
Junger came from television sitcoms and later helmed Black Knight and If Only.
Q 03On what date did the film open in US theaters?
31 March 1999
It landed the same weekend as The Matrix and still opened to more than $8 million.
Q 04Which screenwriting duo wrote the script?
Karen McCullah and Kirsten Smith
The pair began writing together over the phone before ever meeting in person, drafting their first script on cocktail napkins.
Q 05What is Kat Stratford's full first name?
Katarina
The spelling nods to Katherina, the shrew of Shakespeare's original, without copying it exactly.
Q 06Who plays Cameron James, the new kid smitten with Bianca?
Joseph Gordon-Levitt
He was still starring as Tommy Solomon on 3rd Rock from the Sun when the film came out.
Q 07Which actress plays the popular younger sister, Bianca Stratford?
Larisa Oleynik
She was 17 during filming and graduated from high school in California the same year the film opened.
Q 08Before playing Bianca, the actress had been the title star of which Nickelodeon series?
The Secret World of Alex Mack
Alex Mack ran from 1994 to 1998, ending only months before shooting began on the film.
Q 09Patrick Verona is described as a bad boy from which country?
Australia
The role was written before Heath Ledger was cast, so his native accent was a happy match for the character.
Q 10Who plays Ms. Perky, the school guidance counselor?
Allison Janney
The West Wing premiered later that same year and made her one of TV's most decorated actresses.
Q 11What does Ms. Perky work on at her desk between student meetings?
Racy novels
The counselor is more interested in her manuscript than in the students filing through her office.
Q 12Which actress plays Chastity Church, Bianca's best friend?
Gabrielle Union
She appeared in two 1999 teen films, this one and She's All That, before leading Bring It On.
Q 13The actress who plays Chastity had her breakthrough the following year in which cheerleading film?
Bring It On
Playing Isis, captain of the East Compton Clovers, turned a supporting player into a lead.
Q 21Kat's friend Mandella is a devoted fan of which writer?
William Shakespeare
She even wears a period costume to the prom to match her literary obsession.
Q 22Party host Bogey Lowenstein belongs to a clique of aspiring what?
MBAs
The golf-loving future business majors are one of several cliques Michael maps out for Cameron on his first day.
Q 23At the party, a drunk Kat opens up to Patrick about wanting to do what?
Form a band
The confession pays off in the final scene, when the money that bought her also buys her instrument.
Q 14Andrew Keegan's affluent, self-absorbed character aspires to what career?
Model
His vanity pays off in the plot: he bankrolls the whole scheme to free up Bianca's dating life.
Q 15Which actor plays Cameron's geeky friend who masterminds the plan?
David Krumholtz
He later spent six seasons as math genius Charlie Eppes on Numb3rs.
Q 16The actor who ended up playing Cameron originally auditioned for that role and which other one?
Michael Eckman
He was reluctant to do a high-school film at all, then landed Cameron once the other part was cast.
Q 17What is Walter Stratford's profession?
Obstetrician
His job fuels his paranoia: he has seen too many teenage pregnancies to let his daughters date.
Q 18What condition does Walter attach before Bianca may go out with boys?
Her sister Kat must date too
He assumes Kat's hostility to boys makes the condition impossible, which is exactly what sets the plot in motion.
Q 19Bianca is in which year of high school when the story begins?
Sophomore
Kat, by contrast, is a senior counting the days until she can leave town for college.
Q 20Who secretly pays Patrick to take Kat out?
Joey Donner
The payments escalate: a second, larger sum is offered to get Kat to the prom.
Q 24Which song does Patrick sing to Kat from the stadium bleachers?
Can't Take My Eyes Off You
The school marching band backs him up while he dodges the campus security guards.
Q 25Which song was nearly used for the bleacher serenade before the Frankie Valli number was chosen?
I Touch Myself
The runner-up was by the Australian band Divinyls, which would have suited the character's nationality.
Q 26How many takes did the bleacher serenade scene require?
3
The most replayed sequence in the film was in the can almost immediately.
Q 27Heath Ledger's serenade earned him an MTV Movie Award nomination in which category?
Best Musical Performance
Julia Stiles went one better at the same 2000 ceremony and actually took home a trophy.
Q 28At the 2000 MTV Movie Awards, Julia Stiles won which prize?
Breakthrough Female Performance
The Chicago Film Critics Association also named her the most promising actress of 1999.
Q 29How does Kat repay Patrick after the serenade?
She helps him escape detention
The distraction she creates for the teacher is one of the film's most quoted moments.
Q 30Which real band performs at Club Skunk?
Letters to Cleo
The Boston group also plays a rooftop cover over the closing credits and was billed as Kat's favorite band.