Clueless is one of the most iconic teen films of all time, but it is also a notable adaptation of a classic work of British literature, Jane Austen's Emma. Emma tells the story of a beautiful, wealthy woman, who takes matchmaking and social machinations to mildly hubristic ends, and finds herself entangled in romance despite her best wishes. Like Cher Horowitz, Emma Woodhouse, Austen's protagonist, has a deep compassion for the poorer classes, but a sometimes "clueless" investment in her own class position and a daft perception of her own privilege. Additionally, just as Cher Horowitz vows to remain a virgin and has a strong dislike for high school boys before finding herself in love with Josh, Emma Woodhouse vows never to marry before ending up marrying her intellectual rival George Knightley.
While the average teen viewer of Clueless may not be likely to spot its parallels with Austen's novel, the parallels are numerous and the adaptation is markedly faithful. The plot follows roughly the same trajectory as Austen's novel. Additionally, Austen's treatment of class in Georgian-Regency England is perfectly transferred to the setting of a Beverly Hills high school in the mid-1990s. In an article on the adaptational overlaps between the two stories, journalist Tasha Robinson writes, "Clueless’ brilliance as an adaptation comes from the way Heckerling saw how precisely Austen’s country village parallels a modern-day high school, another environment where a small group of people are tied together by circumstance in a social setting where class and personality creates artificial rifts, nearly impenetrable except when the participants see some benefit in penetrating them." Austen's novel and Heckerling's film are similar not only in narrative and assemblage of characters, but also in their nuanced depictions of class dynamics and the selfishness manifested by such heavily classed environments. Indeed, what better place to look cuttingly at micro-class distinctions and how they affect courtship rituals than in a teen movie set in Beverly Hills?
In addition to their parallel treatments of class, both Emma and Clueless show the limits of the subjective mind and the human ego, as well as the hubris of seeking to control one's environment and social circles without measure. Both Emma Woodhouse and Cher Horowitz believe that they know better than others in nearly every circumstance. Their lack of humility gives them pluck and a proactive helpfulness in their respective communities, but at times, they are helpful when no help is needed. In another article on the parallels between Emma and Clueless, Sarah Seltzer writes that Emma is "not merely a novel about the perceptive limits of being young, but a novel about a condition that endures throughout life—that of being trapped in our own consciousness, hindered by the powerful screens of our egos from clear vision." This analysis of the novel begs comparison with Cher's evolving inner monologue, as she realizes just how "clueless" she has been all along. Walking along Rodeo Drive, Cher thinks, "Everything I think and everything I do is wrong. I was wrong about Elton, I was wrong about Christian, and now Josh hated me. It all boiled down to one inevitable conclusion, I was just totally clueless." Like Emma Woodhouse before her, Cher must drop her presumptuousness and controlling machinations in favor of contemplation and self-analysis, examining more closely her own desires and intuitions, and listening to her own heart without presuming to know what is best for others.