From Shakespearean street gangs to Beverly Hills matchmaking, these classic movies sneakily retell timeless literary tales with a modern twist.
You know those movies you’ve watched a dozen times, quoting the lines, humming the soundtrack… only to find out later they’re actually based on some dusty old book you may or may not have skimmed in school? Turns out Hollywood has been doing this for decades, just taking the bones of great literature, dressing them up in contemporary clothes, and letting them loose on our screens. And we lap it up.
Some of the connections are pretty obvious, but others might just surprise you. So let’s crack it open and see what we’ve really been watching on the silver screen.
West Side Story (2021)
This might be one of the more obvious ones, after all, it is just Shakespeare with jazz hands and street gangs.
West Side Story swaps Verona for 1950s New York, the Montagues and Capulets for the Jets and the Sharks, and swords for switchblades. The doomed romance between Tony and Maria follows the same arc as Romeo and Juliet, right down to the tragic ending that still makes you want to yell “Don’t go in there!” at the screen.
The most recent 2021 version, directed by Steven Spielberg, keeps Leonard Bernstein’s music and Stephen Sondheim’s lyrics but adds fresh choreography, richer backstories, and sharper social commentary on race, immigration, and belonging. It won awards and became an instant classic, proving that even after 400 years, Shakespeare’s tale of love caught in the crossfire of hate still hits home, only now with extra pirouettes. (Which we absolutely ate up!)
Bridget Jones’s Diary (2001)
Helen Fielding’s novel was already a cheeky homage to Jane Austen, but the movie really plays into it, casting Colin Firth as Mark Darcy, a modern-day stand-in for Austen’s Mr. Darcy. The parallels are brilliant: awkward first meetings, cutting (yet not-so-secretly flirty) remarks, misunderstandings galore, and the eventual realization that under that deliciously frosty exterior lies the perfect romantic hero.
Bridget, like Austen’s Elizabeth Bennet, is smart, self-aware, and occasionally spectacularly wrong about people. The big difference? Austen’s heroine never had to battle with mini-breaks, embarrassing holiday sweaters, or the perils of answering your work phone after too much wine (although we’re sure it would’ve gone the same way). But the heart of the story, the essence of love overcoming pride and prejudice, well, that remains intact.
She’s All That (1999)
It’s not just a ‘90s teen rom-com. It’s not just a classic, it’s Shaw’s classic play Pygmalion in baggy jeans and bucket hats. The story is simple: can popular jock Zack turn artsy, paint-covered Laney into prom queen material? The quintessential transformation montage is pure ‘90s magic: haircut, contacts, a killer red dress, and yes, the staircase moment is iconic.
Like Pygmalion, the story plays with themes of identity, perception, and whether we’re defined by how others see us. Also, it gave us Sixpence None the Richer’s “Kiss Me,” which deserves its own place in cinema history.
10 Things I Hate About You (1999)
High school in the ‘90s was clearly prime real estate for Shakespeare adaptations. In this one, Padua High stands in for Padua, Italy, and the “shrew” is Kat Stratford, a fiercely independent, sharp-tongued feminist who has zero interest in dating. Enter Patrick Verona, also known as Heath Ledger, in full charming-rogue mode, who has been bribed to woo her so her younger sister Bianca can date.
The film keeps the battle-of-wits energy from Shakespeare’s original but swaps out the outdated “taming” angle for a more modern love story built on mutual respect. And yes, Ledger’s serenade of “Can’t Take My Eyes Off You” in the school stadium is still one of the greatest rom-com gestures of all time.
Clueless (1995)
Cher Horowitz is pretty much Beverly Hills royalty. She’s rich, popular, and determined to use her matchmaking skills for good… even when they’re not exactly asked for. Just like Austen’s Emma Woodhouse, Cher frequently meddles in other people’s love lives, often with hilarious (and less than ideal) results, until she eventually realizes she might have overlooked her own perfect match right under her nose.
The script is endlessly quotable (“As if!”) and somehow manages to keep Austen’s wit while translating it into the slang and shopping habits of the mid-’90s. It’s proof that a 200-year-old social comedy can thrive just as well in the food court as in the drawing room.
The Lion King (1994)
Yes, really. The Lion King is Disney’s version of Hamlet. You’ve got the prince (Simba), the ghostly father urging revenge (Mufasa), the treacherous uncle (Scar), and the quest to reclaim the throne. Granted, Hamlet didn’t have singing meerkats or Elton John ballads (although students might enjoy studying it more if it did), but the bones are all there.
It is kind of genius how the film takes the dark, bloody original and turns it into a family-friendly epic without losing any of the emotional weight. The themes of grief, responsibility, and destiny are all still there, and with the additional benefit of Timon and Pumbaa’s “Hakuna Matata”, which is a far better life philosophy than anything Shakespeare offered.
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Millie Ramm
Millie has been writing since she was a child, and has spent more time with her nose in books than anywhere else. She has been ghostwriting novels and editing for the past few years, and when not working she is curled up with her cats, looking for her next read.
