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1. Who plays Cher Horowitz?
Alicia Silverstone
Silverstone was a teenager known mostly from Aerosmith videos, including Cryin', when she was cast, and the part made her a star. Witherspoon later played a similar sunny overachiever, Elle Woods in Legally Blonde.
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2. Who wrote and directed Clueless?
Amy Heckerling
Heckerling had made Fast Times at Ridgemont High more than a decade earlier, and this one also launched a run of young careers. The script began as a television pitch, and afterward Heckerling turned Clueless into a series that ran three seasons.
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3. Which Jane Austen novel inspired the film?
Emma
Cher is Emma Woodhouse, Tai is Harriet Smith and Josh is the Knightley figure, while Elton keeps the name of Austen's social climbing vicar. Heckerling wanted a sturdy plot to hang the comedy on and took Austen's almost beat for beat.
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4. Which designer made the dress Cher refuses to lie down in when she is robbed?
Alaïa
Elton leaves her in a Valley parking lot after she turns him down, and a mugger orders her onto the ground. 'This is an Alaïa,' she protests, which gets her nowhere. Calvin Klein is the label on the dress her father mistakes for underwear.
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5. Who plays Tai, the new student?
Brittany Murphy
Murphy had done mostly television before this, and Tai's swing from flannel-wearing newcomer to the rival who calls Cher 'a virgin who can't drive' is the film's biggest arc. Claire Danes was playing a very different teenager on My So-Called Life at the time.
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6. Who plays Josh?
Paul Rudd
It was one of Rudd's first film roles, and Josh, the college student who reads Nietzsche and watches CNN, set the template for the amiable parts that followed. Jeremy Sisto and Breckin Meyer are in the film too, as Elton and Travis.
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7. How is Josh connected to Cher's family?
He is her former stepbrother
Josh's mother was briefly married to Mel, who insists Josh is still family, which is why he keeps turning up for dinner and to help Mel with work. Austen's Emma and Knightley are also joined by marriage, through her sister and his brother.
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8. What is Cher's father's profession?
Lawyer
Mel Horowitz is a litigator, 'the scariest kind of lawyer' in Cher's words, and Dan Hedaya plays him with a permanent scowl. When she argues a C-plus up to an A-minus, Mel says he could not be happier if it were based on real grades.
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9. Which Los Angeles area is home to Cher?
Beverly Hills
The Horowitz house is a Beverly Hills mansion with columns Cher dates all the way back to 1972, and the Valley is another country as far as she is concerned. Echo Park, Silver Lake and Venice are all real Los Angeles neighborhoods, just not ones she visits.
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10. What helps Cher choose outfits in the opening?
A computer wardrobe program
The program shows outfits on a photo of Cher and flags a bad combination as a mismatch, a gag that predicted a whole category of apps by a couple of decades. The closet behind her is motorized, which is where the rotating closet idea comes from.
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11. Which teachers does Cher try to match up?
Mr. Hall and Miss Geist
Hall teaches debate and gave Cher the grade she wants raised, so she and Dionne forge love notes and leave them on Geist's desk to put him in a better mood. Rooney, Vernon and Norbury are teachers from Ferris Bueller, The Breakfast Club and Mean Girls.
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12. What type of hobby defines Travis at school?
Skateboarding
Travis Birkenstock is the school's resident stoner skater, and Cher steers Tai toward Elton instead, which is the matchmaking that goes wrong. By the end he has sworn off drugs and is competing in a skate contest with Tai cheering him on.
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13. What goes wrong during Cher's driving test?
She fails it
She scrapes a parked car, nearly flattens a cyclist and cannot talk the examiner round, which is a first for her. The same afternoon brings a fight with Tai, and the two blows together send her on a soul-searching walk down Rodeo Drive.
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14. What short phrase is Cher especially associated with?
As if!
She first says it when a boy puts his arm around her in the hallway, and it brushes him off along with a flick of the hand. The film's lexicon spread almost as widely: 'Baldwin' for a handsome man, 'Monet' for someone who looks good only from a distance.
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15. What does Cher realize about Christian?
He is gay
Cher spends days trying to seduce him, and asked whether she likes Billie Holiday, answers that she loves him. Murray finally spells it out in Dionne's car. In Austen, his counterpart Frank Churchill is unavailable for a different reason, a secret engagement.
