Thirty years ago (yes, 30!) on July 19th, 1995, movie history was made with the release of teen rom-com Clueless. Starring some of my favorite actors—such as Alicia Silverstone, the late Brittany Murphy, and Paul Rudd—the clever, quotable contemporary retelling of Jane Austen’s Emma continues to ensnare fans to this day.
Playing the unforgettable, self-appointed Beverly Hills princess Cher Horowitz, Silverstone captured the hearts of so many ’90s tweens and teens with her misguided—but well-intentioned—life lessons. For example: What to do if you’e being mugged, and you’re wearing a very expensive outfit? Get on the ground, of course, but first appeal to the mugger’s sense of fashion. Or should you do if your hot guy friend is vibing with your newest bestie? Time to play matchmaker!
It’s hard to fathom that such an iconic mid-’90s movie was inspired by Emma, Jane Austen’s 1819 classic. Young English socialite Emma may not have had to deal with the same pressures as Beverly Hills it-girl Cher, like learning to drive in platforms, teachers lowballing her grades, or “ensemble-y challenged" mean girls. Yet the two are alike in more ways than one. Both Emma and Cher hail from a prestigious, privileged background, struggle with the oh-so awkward moments of meddling and matchmaking gone wrong, find their attempted social elevations going awry, and, along the way, demonstrate a complete misjudgment of other characters. Though they're separated by nearly 100 years, oddly enough both young women clearly prove that, while the world may change, the embarrassments and mishaps of coming-of-age remain very similar.
In celebration of three decades of Clueless, I'm honoring this perennial favorite film with a list of unforgettable leading ladies who demonstrate that, even in the most awkward situations, growth and a happy ending are never too far behind.
Listening recommendations for Clueless fans
Serena van der Woodsen and Blair Waldorf are living the upper echelon lifestyle like our Beverly Hills resident, Cher, except they’re taking the Upper East Side of the big city by storm with all of their dramas and truths being blasted on an anonymous gossip site.
Cher and Elana both endured the loss of a parent at a young age, however that hasn’t stopped them from living like life's a “Noxzema commercial.” Then again, the 90210 zip code area isn't running rampant with hot vampires like Elana’s hometown of Mystic Falls, Virigina...
Unlike our favorite high school matchmaker Cher, self-proclaimed matchmaker Dabney Kimball Beech is out of her teen years. However, both excel at setting up their friends and loved ones. For themselves? Not so much!
Boy troubles are at an ultimate high for both Belly and Cher. But what's worse: choosing between your two close brotherly friends (who also happen to be actual brothers themselves) or falling for your own step brother?
Alesha and Cher both lack nothing in the social life and success departments. While they both struggle in the area of love and dating, they're willing to pull out all the stops to get their happy ending.
Unlikely love blossoms for both Liz Buxbaum and Cher Horowitz while they're in the process of scheming and planning to get their guy—even if it means they'll make some unlikely allies to get what they want.
Kristen and Cher share high standards for their men. For high school attendee Cher, it’s absolutely no high school boys. (It’s them, not her.) For Kristen, it's completely understandable—especially with the secret she’s harboring.
Bridget Jones may not have the smooth, easy-going life that Cher holds so near and dear. But Cher's privileges and perfections aside, both of these leading ladies struggle with a quest for self-improvement.
Carrie Bradshaw is an it-girl once she gets to NYC. But long before she was that woman, she was just a girl, living in a small town. Both Cher and Carrie embody coming-of-age pains and hard-learned lessons.
Cher struggles with finding Mr. Right, even with all her beauty and money. She finally finds her love, however, in an unlikely person always near and dear to her. Quinn shares a similar love story as she teams up with a foe to find out who’s been blackmailing her with her missing journal of love notes.
To hear Cher tell it, she lives by A Tale of Two Cities, specifically by her most notable misquote,:“'Tis a far, far better thing doing stuff for other people.” However, this tale about French elites handling a fall from grace in the revolution also reminds me of Cher's struggle to keep her crown from the uprising of her latest pet project.
Unlike Cher, Jessica Darling doesn’t care for shopping, love, or really anything stereotypically associated with girls. However, that doesn’t stop Jessica from unexpectedly finding her handsome dream man, a realization that hits her just like it hit Cher and Josh.
Following the same energy as Clueless, Every Summer After explores the idea that love may not be that far from you all along. Now it may not be your step-brother, but it could be that best friend you’ve been close to forever.
Even though they're young, both Cher and Andie believe they have it all figured out. However, both learn that there’s no plan or set timeline when it comes to the complexities of life. And sometimes, going with the flow works out even better.
Big feelings. An unexpected crush. Cara Bastone's Better Luck Next Time may not be quite step-brother-to-lover like Cher, but this enemies-to- lovers rom-com hits the same sweet spot. (And it's a lot a less weird).
