When the first lockdown of the pandemic hit, a group of my college friends decided to have weekly Zoom calls for Rom Com Movie Night, so we could stay connected and enjoy some classics of the genre. I was a Romantic Comedy casual in those days, more likely to recommend a “technically a Rom Com” movie to the group, but happy to be included and given a proper education in the art of the Romantic Comedy. After graduation, our numbers gradually dwindled, until it was me, KaVonna, and Sabrina still meeting every Friday to catch up and watch movies. We picked our way through the genre staples and scrutinized every new film we could access on streaming. We started the ‘check’ list, calling out common tropes like “dead mom” or “last minute airport confession.” We sometimes wouldn’t watch anything at all, and just check in on how our lives were going. It’s one of the highlights of my week.
And now there’s a podcast episode to commemorate it! I was invited to be a guest on KaVonna’s fabulous podcast, the Introvert’s Social Hour, where she gets social for an hour a week and discusses topics ranging from being a creative, adulting as an introvert, and more! In this episode, you will hear two seasoned Rom Com pros and me discussing our Top 5 Romantic Comedy movies of all time. I did include some of my ‘technically a Rom Com’ titles, but I was proud to rank some genre classics high on my list, after three years’ study. I hope you have as much fun listening as this was to record, and make the Introvert’s Social Hour one of your weekly staples.
Now! Check out my list of my top 5 Rom Coms, and maybe add a few to your ‘Must Watch’
#5 – Rye Lane
About: Dom (David Jonsson) and Yas (Vivian Oparah) meet at a mutual friend’s art show, and get to know each other over one interesting day, traipsing through in South London and talking about career aspirations, young adult life, and heartbreak. As they grow closer, they start to catch feelings, but can you really know someone after one day?
Rye Lane is a new Romantic Comedy on the block, and it made my list because it is a great example of a modern take on the genre. The charming dynamic between the main couple carries this film, showing how easy it is to bond with a stranger over shared young adult angst (and how its even easier to let a little white lie build, when you’re trying to impress that stranger). The style is a delight, with creative shot composition, strong color story, and highly effective use of flashbacks to show the artifice that can sneak in when we stretch (or completely change) the truth.
#4 – The Holiday
About: In Los Angeles, California, Amanda Woods (Cameron Diaz) dumps her boyfriend right before Christmas, after finding out he cheated on her. In a Surrey, England, Iris Simpkins (Kate Winslet) is in her own romantic trouble, after learning her ex-boyfriend (who still emails her constantly, hinting that he might want to get back together) is engaged to another woman. Amanda and Iris connect online, and set up a house swap for the Christmas holiday. Amanda quickly doubts her rash decision, but after meeting Graham (Jude Law), Iris’ handsome brother, and having a one night stand with him, decides to give England another shot. In LA, Iris meets Arthur (Eli Wallach), an elderly neighbor of Amanda’s, who used to be a screenwriter, and the two become quick friends, discussing old movies with strong female leads full of gumption. She also befriends Miles (Jack Black), a coworker of Amanda’s ex, when he comes to pick up some of his things. As the holiday season spins on, both women learn a lot about themselves in their new surroundings, and rethink what they want from romance.
The Holiday is an adorable Christmas Romantic Comedy, but I think it can be enjoyed any time of year. The dual storyline is well-balanced, allowing both leading ladies to have their own character arc, learn their own lessons, and interact with the rest of the fabulous cast of characters without anything feeling rushed or forced. The film also utilizes the Los Angeles setting and film industry backdrop well, implementing fun in-movie trailers when Amanda rethinks her life, and a gorgeous score including character themes composed by Miles for Iris and Arthur. There’s also a scene where they essentially let Jack Black loose in a Blockbuster and he scats/sings famous film scores that I always enjoy.
#3 – But I’m a Cheerleader
About: Megan Bloomfield (Natasha Lyonne) thinks she’s a typical teenager, a cheerleader with a football-playing boyfriend, Jared, and parents who love her, until they host an intervention. Everyone around her thinks she’s a lesbian, and her religious parents plan to send her to True Directions, a two-month-long conversion therapy camp to “straighten her out.” The five-step program at True Directions teaches campers to reject their homosexuality (after searching for the root of it) and embrace heteronormative ideas of gender roles. While at the camp, Megan meets Graham Eaton (Clea DuVall), another girl in the program who knows the camp is bullshit, but is going through with it to avoid being disowned by her family. Megan discovers her sexual orientation and begins to fall for Graham, in the very place she was meant to reject lesbianism. After meeting former students of True Directions and now ex-ex-gays and exploring gay culture, Megan comes to accept her identity, but Graham isn’t ready to do the same. Can Megan save Graham from a life of unhappiness?
But I’m a Cheerleader has my entire heart. You would be surprised how charming and funny a film set at a gay conversion camp could be, but this Rom Com puts the camp in conversion camp. It’s parody style shines a light on the absurd notions that drive heteronormative anti-LGBT camps like True Directions, and has you laughing throughout with punch-up jokes. Its set design, costuming, and color story (the strict pink and blues of the camp, the flamboyant rainbow of the ex-ex-gay’s house and the gay club, and the striking orange of Megan’s cheer uniform) all enhance the story while being a delight to look at. Lastly, my favorite aspect of this film is how it uses the medium of Romantic Comedy to challenge heteronormativity and show how gay love (and lust) can be the key to freedom, despite all the hardships the world throws at queer people.
#2 – Scott Pilgrim vs. The World
About: Scott Pilgrim(Michael Cera) is a 22-year-old with no job, a terrible band, and a high school girlfriend. He’s not exactly living the dream. But when he starts literally dreaming of the perfect girl, and then spots her at a party, Scott becomes fixated. Ramona Flowers (Mary Elizabeth Winstead)… Against all odds, Scott manages to win her over, and she even agrees to date him! Problem is, dating Ramona means he has to defeat each of her seven evil exes, on top of competing in the Battle of the Bands for his big break. And then there’s that high-school girlfriend to worry about… What has Scott gotten himself into?
Scott Pilgrim vs. The World ranks so highly on my list because it’s also one of my favorite films of all time. Which is a tall order, for a style of story (everyman gets the girl who’s way out of his league) that I don’t usually resonate with. But this film is snappy, fantastically shot, and has a comic book and video game style that makes every viewing a spectacle. It injects a story about dealing with the baggage of exes with high-action and hilarious, well-timed quips, and even manages to sneak in a lesson about the power of love, and the over-powered power of self respect, and owning up to how you’ve hurt the people around you.
#1 – 27 Dresses
About: Jane Nichols (Katherine Heigl) embodies the saying “Always the Bridesmaid, Never the Bride.” She’s been in 27 weddings, inspired by the joy of being there for someone of their special day. She helps with everything from the planning to doing a fit check on a wedding dress because she happens to be the same size, knowing that when it’s her time, all the friends she’s been there for, will be there for her. On one Saturday night, she’s attending two weddings at once, and after a bouquet toss goes awry, she meets Kevin Doyle (James Marsden), a writer and wedding cynic. They share a cab home, and Jane forgets her planner, and Kevin snoops inside it, and begins to craft a story around Jane life. Because Kevin Doyle isn’t just any writer, he writes for the Commitments section of a local paper, and sees a story about Jane as his way to prove himself and get a better assignment. When Jane’s baby sister Tess (Malin Åkerman) returns to town from a job in Europe, Jane introduces her to her boss, George (Edward Burns), who she’s had an unrequited crush on for years. Sparks fly, and now Tess is spinning lies for Jane’s dream guy, playing the part so well soon they’re engaged. Kevin hears the news and offers to cover their wedding for the paper, and soon catches wind of Jane’s true feelings.
27 Dresses tops my Romantic Comedy list because it is the epitome of Rom Com tropes. We’ve got characters work in publishing/journalism, living in New York, a meet cute, light physical comedy, being hopelessly in love with your boss, file-o-fax Cinderella slipper left behind in a cab, dead mom, crass coworker/best friend (x2), someone who doesn’t believe in love is secretly a romantic, borderline stalking, lying for romance, final act rush to reunite, climax love speech, epilogue wedding, the whole shebang. It’s the blueprint Romantic Comedy plot, with all the classic charms. It was a film that, when I was making this list, I was a little worried about having to rewatch, because many of my childhood favorite films don’t hold up , but this one does. It has a good heart, showing that Jane isn’t a bitter single forever-bridesmaid, but a strong friend who spends all her time taking care of other people. “I think you deserve to be taken care of for a change” gets me choked up every time.
And that’s my list! I hope you enjoyed my Top 5 Recommendations for the Best Romantic Comedies of all time, and maybe even added a few new titles to your list. For a more in-depth discussion on what makes a Romantic Comedy, why these films made my list, and recommendations from two other seasoned Rom Com experts, check out the Introvert’s Social Hour’s episode!
What are your favorite Romantic Comedies of all time?
Do you agree with my list?
Photo by Myke Simon on Unsplash
N. Sowers 
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