Clueless and 8 Other Top 1990s Movies Actually Based on Classic Literature

A ranking of classic teen movies that originated from books

By Samantha Schnurr Nov 04, 2015 8:25 PMTags
Watch: Top 9 Teen Movies Based on Classic Literature

The next time your friend makes fun of you for watching She's All That for the 578th time, kindly remind her you're simply brushing up on your classic literature.

In this roundup of famous films, nine signature 1990s silver screen hits are grouped together based off of their literary origins. While some of the classics, like Easy A and Clueless, are well-known for originating from the literary masterpieces of Nathaniel Hawthorne and Jane Austen, we would have never guessed others in the lineup came to fruition long before Shane West or Julia Stiles arrived in Hollywood.

For example, Freddie Prinze, Jr.'s high-stakes bet to turn the school's token nerd into the shiny prom queen was derived from the same origins as Audrey Hepburn's 1964 My Fair LadyGeorge Bernard Shaw's 1913 Pygmalion

How about O, the 2001 teen basketball drama starring Stiles and the decade's leading heartthrob Josh Hartnettwhich actually turned out to be a modern update of William Shakespeare's 1604 Othello. 

While the film was littered with literary allusions, some fans may have failed to notice that Emma Stone's breakout lead role in the 2010 blockbuster smash hit Easy A was inspired by the high school standard The Scarlet Letter by Nathaniel Hawthorne. We hope this didn't trigger any nightmares about summer nights spent cramming to finish last-minute homework assignments. 

Amanda Bynes, who starred opposite Stone in the film, had an earlier brush with novel adaptations when she took the lead role in the 2006 fan favorite She's the Man, also featuring Channing Tatum. The gender-swapped plot was based off of another Shakespearean classic, Twelfth Night, taking place after a shipwreck instead of the halls of an elite all-male prep school. 

In first place—Alicia Silverstone's iconic role in Clueless. While Cher may have gallivanted around Beverly Hills toting her armful of shopping bags, the heroine who inspired the 1995 cult classic, Jane Austen's headstrong Emma, originally strutted across the pond in England in 1815.

Liketh totally!