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Celebrate Clueless’s 25th Anniversary with 5 Reads Cher Would Totally Love

by  | April 30
Clueless book on couch

I didn’t really get Clueless as a kid, despite its undeniable impact on pop culture and elevating Alicia Silverstone, Paul Rudd, and Brittany Murphy to movie-star status. I was nine when it hit theaters (yes, for anyone doing the math, that makes me an “elder millennial”), so a lot of the humor went over my head, and I was still several years away from reading my first Jane Austen novel. Even watching the film again after college, I found it more interesting as a 90s time capsule than anything else. That all changed recently, when I finally read Emma (I know, I know!) and chased it with a viewing of director Autumn de Wilde’s new movie adaptation, which in turn gave me the urge to try Clueless one more time. You know, for science.

Lo and behold, I absolutely adored Clueless this time around, understanding all in a rush why some Austen scholars consider it the superior Emma adaptation. For all that she’s a thoroughly modern 20th-century girl, Cher, as portrayed by Silverstone, retains all Emma’s frustrating self-absorption—and her endearing good-heartedness. Of course, the film’s sly wit, iconic fashion, and effervescent performances don’t hurt either.

Now that I’ve seen the light, there’s no going back, and I’m fine with it. In fact, I want more! Which is why I’m thrilled to share my Clueless-inspired TBR list with you, just in time for its twenty-fifth (!!!) anniversary.

As If!

As If!

by Jen Chaney

If you, too, are totally, butt-crazy in love with Clueless, then you owe it to yourself to read As If!, an oral history of how the film became the cultural phenomenon it is today. Entertainment reporter Jen Chaney combines countless interviews conducted with the cast, crew, and writer/director Amy Heckerling to narrate, in glorious detail, the project’s journey from script to screen to collective consciousness. Full of behind-the-scenes facts and photos, As If!, an ode to the lasting legacy of Clueless, will make you smile and let the nostalgia wash over you.

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Emma

Emma

by Jane Austen

Since you’re a Clueless fan, you probably already know full well that it’s a modernization of Jane Austen’s beloved Emma. I can’t imagine a better way to experience them than together, so I couldn’t not include the book that brought us all here today. Emma Woodhouse is a polarizing figure in literature, but whether you love her or hate her, you can’t deny that her misadventures in matchmaking are entertaining. Her happily ever after with a certain handsome neighbor is just a bonus for fellow romantics.

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By the Book

By the Book

by Julia Sonneborn

Why stop at one modern Jane Austen retelling? In for a penny, in for a pound, as they say. Julia Sonneborn’s By the Book is to Persuasions to what Clueless is to Emma. Here, spinster Anne Elliot is career-focused English professor Anne Corey, and her one-time love, Adam Martinez, doesn’t just come back into her life as an eminently eligible bachelor, oh no. He’s now her boss. Don’t tell me that Cher wouldn’t be all over the challenge of reuniting the lovers in this second-chance romance.

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Playing with Matches

Playing with Matches

by Hannah Orenstein

Our favorite matchmaker would probably recognize a kindred spirit in Sasha Goldberg, the ambitious heroine of Hannah Orenstein’s novel Playing with Matches. Much like Cher is often oblivious to the damage she’s causing with her well-intentioned schemes, Sasha throws herself into a new matchmaking gig at the elite dating service Bliss without the qualifications one might hope for in the person giving you relationship advice. When her own picture-perfect romance falls apart, Sasha learns she may have been looking for love in the wrong place....

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Difficult Women

Difficult Women

by Roxane Gay

Cher Horowitz, like Emma Woodhouse before her, is the epitome of the “unlikable heroine” archetype. Rich, spoiled, and cocky at the beginning of the story, she’s an acquired taste for sure, but aren’t we all? Roxane Gay’s Difficult Women certainly seems to back me up on this. Featuring stories that center on women from all walks of life and with all sorts of relatable problems, this short story collection is for anyone who appreciates all the different (and sometimes contradictory) sides of the ladies of Clueless.

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Photo Credit // Simon & Schuster

Categories // Bookish ListsMovies

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Heather Waters is an Associate Director of Marketing at Simon & Schuster, where she runs the Get Literary and Tips on Life & Love blogs. She enjoys reading everything from romance to true crime to political memoirs, and in her free time you can often find her binge-watching Netflix, refreshing Twitter every 10 seconds, and listening to the latest episode of the podcast My Favorite Murder.