The word 'rom-com' has become synonymous with over-the-top, cheesy romance movies that hold little weight in the film world. They seem to only ever show off the amazing parts of love and infatuation, with perfect characters, their perfect lives, and perfect endings.
Sometimes romantic comedies take a step beyond their usual predictability, though. They transcend their genre while still succeeding as masterpieces of the rom-com formula. Whether it's through multi-faceted characters, iconic costumes, or even shaping pop culture itself, it is a breath of fresh air when a rom-com delivers more than what's expected.
Miss Congeniality (2000)
Sandra Bullock has always been a master of comedy, and she truly shined in Miss Congeniality as Gracie Lou Freebush: the undercover FBI agent with a heart of gold. Although she could easily take down any of her colleagues in a boxing ring, the hardest part about her job was transforming into the beautiful and charming, Gracie Hart with her iconic purple Hervé Léger dress and questionable wine glass talents.
It was Bullock's dry humor and natural chemistry with co-stars Michael Caine, Candace Bergen, and Benjamin Bratt, that made the story so fun. Gracie was a stunning woman who had her dream job, and yet she still failed in places in her life. The film also gave its female characters strong personalities. Who could forget Miss Rhode Island's memorable quote, “April 25th — because it's not too hot, not too cold. All you need is a light jacket!”
Legally Blonde (2001)
Let's face it: Legally Blonde is still the reigning movie of the early 2000s rom-coms. Elle Woods (Reese Witherspoon) began as Delta Nu Barbie and studied her way up to conquer Harvard. Anything for love, right? The greatest part about this movie wasn't that she found love though. Elle eventually ditches Warner Huntington III and uses her charming talents to make friends out of her enemies, win a high-profile court case, and become a lawyer on her own merit.
Legally Blonde helped birth a generation of girls that rightfully put their dreams and goals ahead of anything else. The movie is still doing that to this day, with its brilliant screenwriting, smart humor disguised as ditzy and blonde, and amazingly pink fashions that still inspire.
Clueless (1995)
Clueless was released 27 years ago, and still rules as the edgier cousin to the rest of the 90s teen comedies. Cher (Alicia Silverstone) has a love interest who turns out to be gay, Dion (Stacey Dash) struggles with perpetually underdressed men, and Tai (Brittany Murphy) is transformed into a snarky Beverly Hills teen who just loves skater boys and Marvin the Martian. No other rom-com at the time could match Amy Heckerling's clever writing.
Clueless came out amongst a slew of teen movies where the biggest problems were school bullies, unrequited crushes, and jocks vs. nerds. Its release changed the genre and completely took over teen culture with its designer fashion, sharp humor and attitude, and iconic catchphrases such as, “As if!” and “You're a virgin who can't drive.” The movie mastered colorful aesthetics and witty writing as well, like Cher's incredibly funny and ditzy Haitian monologue.
Penelope (2007)
A woman with a pig snout for a nose sounds like a strange and somewhat off-putting movie. Cursed at birth through her bloodline and sheltered inside her entire life, Penelope is a girl who must find her Prince Charming in the most unconventional of ways. And that's exactly what 2007's Penelope mastered.
Penelope was a charming and sharp film that took all the stylings of fairy tales and turned them into a wondrous love story between an eternally hopeful Penelope and sleazy, gambling liar Johnny. Christina Ricci, Catherine O'Hara, and James McAvoy made an unforgettable combo onscreen. Getting to see Penelope venture out of her house and conquer the world that had dealt her so much grief made this simply magical.
One Fine Day (1996)
On the outside, this movie seems like an ordinary romantic comedy. It was the star power of its actors that made it a superior, truly feel-good experience. Michelle Pfeiffer played the ambitiously hard-headed Melanie Parker to George Clooney's brash and laid-back Jack Taylor, both struggling as single parents on the day that their children miss their field trip.
One Fine Day mastered the genre through its realistic life problems that many could relate to. It turned the stress of being a single parent into funny and heartwarming moments, all while its stars dripped with dazzling chemistry. Pfeiffer walking around New York in her business suit and her son's dinosaur t-shirt was just quirky enough to maybe want to fashion your own.
Ever After (1998)
Like other romcoms based on fairytales, Ever After had a very happy ending. Unlike most though, it took place in Renaissance France and had the production design of a dream. The charismatic Drew Barrymore brought Danielle to life, a beautiful and vibrant young woman forced into servitude when her father dies. She accidentally meets the prince, Henry (Dougray Scott), and the rest is history.
Ever After sets itself apart by taking the fairy-tale romance quite literally to screen. The movie looks like something out of a Shakespearean fantasy, with stunning costume pieces, flowing princess dresses, and dazzling fairy wings.
How to Lose a Guy In 10 Days (2003)
How to Lose a Guy In 10 Days was the bright and sunny rom-com that dreams are made of. With Kate Hudson's bubbly personality and a smart premise in the era of fashion magazines, this movie checked off every box in the genre formula, with panache. Hudson's Andie Anderson had to figure out how to lose Matthew McConaughey's Benjamin Barrie in 10 days. The catch: He's hellbent on doing the exact opposite.
The movie was a fresh twist on rom-coms, where both the typical female and male leads' roles were essentially switched. Andie didn't want to fall in love, and Benjamin had to. It was thoroughly hilarious to watch Andie's attempts at sabotaging a relationship that should have sunk on the first date. Whether it was her causing Bennie-Boo-Boo to get into a fistfight, or Photoshopping their future children's faces into a scrapbook, Hudson and McConaughey were truly unforgettable.
The Wedding Planner (2001)
Jennifer Lopez and Matthew McConaughey are no strangers to rom-coms. And for good reason: no one portrays falling in love quite like them. The Wedding Planner began with Mary's hopes of a dream wedding one day, but never quite achieving it. It ended as one of the most lovely and heartwarming rom-coms of the early 2000s.
Mary was multifaceted with layers of pessimism, fear, and the desire to do the right thing. She played Scrabble and was smart, she was kind and incredibly good at her job – even able to tell, to the exact day, when a marriage would fail based on song choice. Mary did not need saving at all, and that's why her happy ending was so satisfying to watch.
La La Land (2016)
La La Land differed from most romantic comedies in a very visceral way. Nominated for 14 Academy Awards, Emma Stone and Ryan Gosling waltzed across perfectly-lit Los Angeles backgrounds while struggling with love during the crossroads moments of their lives.
Part musical, part drama, and a lot of rom-com, Chazelle's ambitious homage to the silver screen did nearly everything perfectly. Between stunning technical sets of famous Hollywood landmarks, old-Hollywood costume designs, and one of the most heart-wrenching endings of all time, La La Land stands as a testament that rom-coms can be more than the box they are so often relegated to.
Pretty Woman (1990)
Pretty Woman is so much more than just thigh-high leather boots (although those are pretty rad). On the surface, it seems like a modern take on the Cinderella story. But instead of a maid, Cinderella is a prostitute, and Prince Charming is a lonely businessman.
This rags-to-riches story was exactly what Hollywood needed after the fluffiness of 80s romcoms. Pretty Woman dealt with very grown-up themes. It poked at the transactional nature of love and sex, gender roles, and the way society views women. The way in which Vivian (Julia Roberts) gets to make her own choices at the end is what makes it so special.