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

April 30 2020
Share Celebrate Clueless’s 25th Anniversary with 5 Reads Cher Would Totally Love

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.

This post was originally published on GetLiterary.com.

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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As If!
Jen Chaney

Will we ever get tired of Clueless? Ugh, as if! Acclaimed pop culture journalist Jen Chaney celebrates the twentieth anniversary of the classic film’s release in the first book of its kind, weaving together original interviews with writer and director Amy Heckerling; key cast members, including Alicia Silverstone (Cher), Paul Rudd (Josh), Stacey Dash (Dionne), Donald Faison (Murray), Elisa Donovan (Amber), Wallace Shawn (Mr. Hall), Twink Caplan (Ms. Geist and associate producer); and other crucial Clueless players like costume designer Mona May, casting director Marcia Ross, director of photography Bill Pope, former Paramount chairwoman Sherry Lansing, and many more. Cast and crew also pay heartfelt tribute to the late Brittany Murphy, who lit up the screen as Cher’s protégée, Tai. Chaney explores the influence of Jane Austen’s Emma as the unlikely framework for Heckerling’s script, the rigorous casting process (including the future stars who didn’t make the cut), the functional yet fashion-forward wardrobe, the unique slang that drew from the past and coined new phrases for the future, the sun-drenched soundtrack that set the tone, and—above all—the massive amount of work, creativity, and craft that went into making Clueless look so effortlessly bright and glossy. As If! illuminates why plaid skirts and knee socks will never go out of style, and why Clueless remains one of the most beloved comedies of all time.

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MENTIONED IN:

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

By Heather Waters | April 30, 2020

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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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Emma
Jane Austen

If you’re lucky, you were able to see the newest adaptation of Emma before we all had to stop going to movie theaters, but now you have plenty of time to revisit the original text…and see for yourself how bad of a friend Emma is. While she is well-intentioned with her manipulations, Emma’s acts of “kindness” and matchmaking have a tendency not only to backfire on her, but on those she’s allegedly helping. While Jane Austen wrote Emma more than 200 years ago, the complexities of dealing with a mostly well-meaning (if sometimes hurtful) friend can apply in a modern context too (much like we see in the classic 90s film Clueless).

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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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By the Book
Julia Sonneborn

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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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Playing with Matches
Hannah Orenstein

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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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Difficult Women
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.

Amazon logo Barnes & Noble logo Books a Million logo Bookshop logo

MENTIONED IN:

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

By Heather Waters | April 30, 2020

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