Top 10 Movies from the Rom-Com Golden Age
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Top 10 Movies from the Rom-Com Golden Age

VOICE OVER: Samantha Clinch WRITTEN BY: Val Namaki
These are the movies that defined the rom-com golden age. For this list, we'll be looking at the best romantic comedies released between 1990 and 2005. Our countdown includes "Groundhog Day," "Pretty Woman," "Clueless," and more!
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Top 10 Movies From the Rom-Com Golden Age


Welcome to MsMojo, and today we’re counting down our picks for the Top 10 Movies From the RomCom Golden Age.

For this list, we’ll be looking at the best romantic comedies released between 1990 and 2005. Anything from outside this window is excluded, so you won’t find “When Harry Met Sally…” and “(500) Days of Summer” here. We will however be discussing plot points, so consider this your spoiler alert!

Which of these movies is your favorite? Let us know in the comments!

#10: “Groundhog Day” (1993)


We all joked that we were repeatedly reliving the same day in March 2020. But this film’s cranky protagonist Phil Connors actually has to experience Groundhog Day over and over again. Initially using the situation to his advantage, he gradually becomes a person who’s truly able to give and receive love. While the premise is fantastical, the story feels incredibly grounded — no pun intended – thus drawing us in. The sublimely plotted script plays out to such perfection on screen that it’s hard not to feel hopeful by the end of the movie. And the journey is filled with laughs, making its existential and romantic themes feel fun. We definitely wouldn’t complain if we were trapped in a time loop where “Groundhog Day” was always on!

#9: “10 Things I Hate About You” (1999)


Who ever said teen movies weren’t elevated?! The closed-off Kat Stratford’s younger sister Bianca can only date if they both do. So the rebellious Patrick Verona gets compensated to woo Kat, and, naturally, it evolves into something real. Based on “The Taming of the Shrew,” the flick seamlessly incorporates Shakespearan elements while refreshing the plot to make it appealing for modern audiences. And the enthralling narrative is beautifully complemented by the casting. Julia Stiles makes Kat a believable and real heroine, while the late Heath Ledger irresistibly embodies Patrick’s allure. We can’t take our eyes off his serenade! To top it all off, the film flawlessly tees up its climax, ensuring audiences will bawl at every rewatch. Simply put, it’s a masterpiece.

#8: “Sleepless in Seattle” (1993)


A love that’s written in the stars might seem unrealistic, but this Nora Ephron classic makes us believe it’s possible. When the widowed Sam Baldwin’s son Jonah gets him on the radio, listener Annie Reed is smitten. From there, a series of events leads the trio to meet atop the Empire State Building. We can sense that Annie and Sam are meant to be before they ever lay eyes on one another, and their potential alone hooks us. Therein lies the movie’s greatest strength, which is a testament to its thoughtful nature. The dreamy premise is beautifully fueled by anticipation, with Meg Ryan and Tom Hanks’ magnetic performances bringing the whole thing together. Needless to say, this magical tale could soften the biggest cynic up.

#7: “My Best Friend's Wedding” (1997)


We know etiquette dictates that you shouldn’t try to ruin your best friend’s wedding. In Julia Roberts’ defense though, her character Julianne thinks Michael is her soulmate! If you’re thinking this sounds like a classic “man realizes he’s with the wrong woman story,” think again. The movie expertly flips the traditional rom-com on its head, with Julianne resorting to hijinx usually reserved for villains. Yet the character is downright captivating in Roberts’ hands, who makes her multifaceted and interesting to watch. The resulting flick is amazingly compelling and imaginative. It’ll undoubtedly keep you guessing and remind you of the value of friendship, all while melting your heart in unexpected ways. Plus, the soundtrack is epic. Trust us, it’s a must-see affair.

#6: “Pretty Woman” (1990)


Picture this: an escort spends six days and six nights with a rich tycoon, and sparks fly. That’s the uniquely bewitching premise of this film, where Julia Roberts’ Vivian Ward and Richard Gere’s Edward Lewis fall in love. Problematic age gap aside, the characters feel nuanced and layered, prompting us to believe in them. She’s anything but a damsel in distress, and their time together helps him become a better person. The movie is also full of special moments, like that iconic shopping spree, that make for an endlessly entertaining time. Ultimately though, what makes “Pretty Woman,” well, pretty, is the honesty and tenderness that allow the fairytale ending to feel authentic. It’s not one of the decade-defining films of the ‘90s for nothing!

#5: “Bridget Jones's Diary” (2001)


What do you get when you put Renée Zellweger, Colin Firth, and Hugh Grant in a movie together? The answer is a love triangle, and rom-com gold. Bridget Jones is a messy, flawed, and deeply relatable woman who’s trying to figure life out. With us and her diary along for the ride, she dates her skirt-chasing boss Daniel Cleaver, and starts falling for family friend Mark Darcy. The banter, rivalry, and questionable blue soup are impossible to resist. Naturally, there’s also an adorably romantic ending that’ll make you swoon. Most importantly, watching Bridget learn her worth is deeply satisfying. With its humor and heart, this quirky film is too endearing for words, and will seriously make you want to start journaling.

#4: “You've Got Mail” (1998)


This 1998 flick is perfect for when you want to feel warm and fuzzy inside. It stars Meg Ryan as Kathleen Kelly and Tom Hanks as Joe Fox, as his corporate bookstore moves in, destroying her small one. And did we mention the duo have developed feelings for one another through anonymous online correspondence? Their emails alone make the film worth watching! If that’s not enough to convince you, the enemies to lovers trope is also put to excellent use. Plus, a thoughtful, steady pacing carries the film, allowing viewers to embrace its enchanting world. Add in Ryan and Hanks’ stellar on-screen dynamic, and you’ve got a hit. You could even say the story’s charm is reminiscent of, well, a picturesque bookstore.

#3: “Clueless” (1995)


Come for the fashion, but stay for the surprisingly heartfelt story of Cher Horowitz, who finds romance in an unexpected person while meddling in other peoples’ love lives. Taking inspiration from Jane Austen’s “Emma,” this flick delightfully blends genres, bringing the best of the teen movie and romantic comedy together. And it’s a match made in heaven. It succeeds on all fronts, with its lovingly strong-willed protagonist, humorous take on classic tropes, and gripping twists and turns. That’s saying nothing of the star-studded cast, notably featuring Alicia Silverstone, the late Brittany Murphy, and Paul Rudd. As if that wasn’t enough, the movie’s quotability is off the charts. All the pieces of this puzzle fit seamlessly together, and the final product is anything but “Clueless.”

#2: “Notting Hill” (1999)


Who hasn’t dreamt of meeting a celebrity and actually falling in love? When actress Anna Scott ends up in Will Thacker’s corner of the world, that fantasy becomes his reality. What follows is an emotional road that repeatedly tears the pair apart before leading them back to each other. Of course, Julia Roberts and Hugh Grant’s chemistry as the lead duo is unparalleled. Moreover, each scene is intentionally crafted, with the cinematography elevating the spellbinding screenplay to transport us into the characters’ universe. We’d also be remiss not to mention the fact that the film features one of the most poignant and touching lines in romcom history. What can we say? We’re completely defenseless against the charisma that flows out of “Notting Hill.”

Before we unveil our top pick, here are a few honorable mentions.

“My Big Fat Greek Wedding” (2002)
Cultures Clash & Love Overflows as Toula & Ian Decide to Tie the Knot

“There's Something About Mary” (1998)
A Slew of Men Resort to Vile Methods to Earn the Titular Woman’s Affections, & It’s Hard to Keep a Straight Face Watching It Unfold

“Love Actually” (2003)
A Feel-Good Christmas Flick Featuring a Great Ensemble Cast & Numerous Love Stories That’ll Make You Giggle & Cry

“13 Going on 30” (2004)
From Teen to Adult in a Flash, Jenna Rink Learns Who & What Really Matters in This Relatable Tale of Growth & Romance

“While You Were Sleeping” (1995)
You’ll be Grinning From Ear to Ear Watching Lucy Find Love After She Pretends to Be a Comatose Man’s Fiancée

#1: “Four Weddings and a Funeral” (1994)


People get married, and someone dies, but that’s an oversimplification of everything “Four Weddings” brilliantly accomplishes. It’s the timeless tale of a tight-knit group’s search for happiness. Hugh Grant’s Charles finds it with Andie MacDowell’s Carrie, but their forever doesn’t come easy. This romcom is brimming with important lessons about life, love, and loss. Yet it communicates them through gentle, funny writing, a cohesive structure, and first-rate direction, creating a wonderfully joyous and bright viewing experience. Plus, Charles’ offbeat but sincere persona is too darling to ignore, and the ensemble cast’s witty and intelligent contributions are superb. Combine that with the slew of genuinely affecting moments, and you’ll find yourself reaching for the tissues. It’s worth every tear for that thunderbolt feeling, though.
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