Staff Inquiry: Our Favorite Romantic Comedies

Love is in the air throughout February, and that got our writers in the mood to swoon. Not wanting to take things too seriously, we turn our attention for this staff inquiry to one of the stalwarts of cinema: the romantic comedy.

Occasionally disparaged for being light and frothy, we here at Film Inquiry know just how deep they can get, and we also know that the light and frothy ones can be the perfect escape. So without judgement or shame, here are some of our favorite romantic comedies.

Tynan Yanaga – Roman Holiday (1953)

Whenever there is a new monthly inquiry, there is nothing for it but to go with the heart, and since it is the month of Valentine’s this could not be more apropos. Thus, there need be only one answer when it comes to favorite romantic comedies: it’s Roman Holiday.

The reasons are many and highly subjective. Before I ever knew who Audrey Hepburn was or Gregory Peck or William Wyler, I saw that glowing countenance under a tiara and got caught up in a fairy tale.

I am older now – more jaded than I care to admit – and yet the joy of the movies is being able to return on this adventure with Princess Ann and Joe Bradley again and again. It’s not simply that our stars have instantly palpable chemistry (spawning a lifelong friendship), but there is the fleeting sense this cannot last forever. What’s important are the memories made, the sights seen, and the people you get to spend the time with.

As one of the first post-war Hollywood films to shoot on location, Roman Holiday is imbued with a magic unattainable by any other means. The plazas are alive with authentic life and the Vespa rides capture the glorious chaos of such a vibrant city.

Romantic comedies have always been a form of wish fulfillment, a way of living vicariously through characters while getting caught up in the throes of their experience. I am not often a proponent of escapism through movies. For me, movies have always been a reflection to better comprehend our world. However, I will concede Roman Holiday might be an antidote for apathy and fuel to enter back into our lives so we might love others well, whether we’re married or single. As I’ve gotten older that’s what it remains for me.

Emily Wheeler – Imagine Me & You (2005)

In many ways, Imagine Me & You is a relic of its time. The characters use flip phones, rent movies from a video store, and flirt while playing Dance Dance Revolution. Okay, the latter is just ridiculously cheesy, but my point is that this movie’s charm comes directly from its cultural moment. Positioned before mainstream queer cinema and during the time of gay characters dying en masse on film, this by the numbers, happy ending lesbian romance was a respite from the battles being waged.

Sure, other, hard-hitting movies were more important to the gay rights movement (Brokeback Mountain released in the same year), but coming home and vegging out to Piper Perabo and Lena Headey engaging in a tentative romance before unleashing a makeout session on a literal bed of roses is just more satisfying.

Sometimes it’s not about playing the best game imaginable, but about getting to play the game at all. When teenage me saw Imagine Me & You, it was the first time I had seen a queer romance given the same silly, lighthearted treatment that rom-coms normally give to straight couples, and that immediately made an indelible imprint on my mind.

Luke Walpole – About Time (2013)

About Time sees Richard Curtis at his most breathtakingly Curtisian. I can’t think of a higher compliment than that. His whole body of cinematic work is built on the inherent decency of people, the laughter which peppers everyday life, and, of course, the power of love.

Yet About Time is bolder than this and carries the wisdom of a life lived. It’s able to be both charming and wistful; a film which balances Rom and Com but also manages room for pathos. It is wonderfully cast; from the foppish Domhnall Gleeson through to the ever excellent Rachel McAdams and the supreme Bill Nighy.

Curtis’ films have always featured grandstanding moments. The kiss in the rain, the mad dash to the hotel, and the airport sprint all come to mind. But About Time is altogether much calmer. It has its big moments, but much like the central theme of the film itself, it invites you to pause and appreciate the quieter interactions.

As a result, you can enjoy About Time on multiple levels. As a piece of comedy, it leaves you grinning for the vast majority of the run time. As a romance, it carries the same bumbling earnestness which has become a hallmark of Curtis’ work. But it is also a thoughtful, heartwarming film which gives you space to think meditatively about time.

Yes it’s a bit twee, yes it’s got a few morally ambiguous moments, but it is also effortlessly brilliant.

Kristy Strouse – Eternal Sunshine of the Spotless Mind (2004)

I have to say, singling out my favorite romantic comedy is not an easy task. As I labored over this decision, some of those that I came up with weren’t necessarily comedies. So, suffice it to say, this isn’t necessarily my favorite romance. I have to mention, another one of my favorites that I almost chose was Reality Bites. This 90’s comedy left a huge impression in my teenage years.

However, when I think of number one? I’ve got to include points for creativity, originality, and general weirdness. Yes, it is Eternal Sunshine of the Spotless Mind. It’s wonderfully audacious, and it packs some powerful comedic and emotional performances from its leads.

This auspicious romance that delightfully infuses real emotion and difficult questions (with love what else is there?) instantly became a romantic comedy classic. Joel (Jim Carrey) and Clementine (Kate Winslet) fall in love, but ultimately, they break up. Their broken hearts persuade them to a sense of finality not often delved into on screen as they erase their memories of one another. What follows is a dream-like tale through first meets, second meets, and all of the gushy in-between. It’s a bit raw but nevertheless beautiful. If you want a film that captures the feel-good moments and the harsh realities of love, Eternal Sunshine is it. Carrey and Winslet, as well as all of their excellent co-stars, commit to these yearning, odd, characters. Try it and see if you don’t get the feels.

Julian Rosenthal – Annie Hall (1977)

Woody Allen’s work has, quite rightfully, undergone a pretty major shift the past few years in terms of public opinion. Part of this is due to the inherently short shelf-life of comedy, which lives and dies depending on cultural setting and part of it Allen’s own history being recontextualized in the age of #MeToo.

But Annie Hall, somehow, remains timeless. I think that’s because it has always been unconventional, both in the joke delivery and in the way it handles the central romantic plot.

Yes, there are countless classic Woodyisms and throwaway one-liners of the type that Allen was always known for, but in Annie Hall he is much more creative in the way he uses the language of cinema to set up and deliver punchlines. In a scene that I’m sure will resonate with many Film Inquiry readers, Allen gets annoyed while waiting in line at the theater and breaks the fourth wall to complain about the film opinions of a boorish man droning on behind him.

Annie Hall is equally unconventional as a romance. After possibly the best meet-cute moment in all of cinema – Diane Keaton as Annie could teach a masterclass in nervous laughter – Allen spends most of the remainder of the film convincing the viewer that Allen and Annie shouldn’t end up together. We see them fight, breakup, and get back together in a revolving cycle of disappointment, and by the end we’re almost glad to see them walk away.

And yet, a bittersweet ending montage reminds us of all the charmed, genuinely happy moments we forgot about among all the fighting.

Love is messy, weird, and sometimes downright contradictory, and Annie Hall shows us that rom-coms can be satisfying even when the couple doesn’t stay together. You can be happy without having a happily ever after.

Matthew Roe – Harold and Maude (1971)

Hal Ashby was one of the greatest filmmakers to have ever worked in the medium, and his filmography throughout the turbulent 1970s further solidifies this fact.

Initially created as screenwriter Colin Higgins’ master’s thesis in the late 1960s, Harold and Maude eventually found its way to Ashby. He would only direct the film when he received Higgins’ blessing, and in turn made him a co-producer so that he could learn on-set how to handle a movie shoot.

Harold (Bud Cort) is a death-obsessed young man who stages fake suicide attempts, drives a modified hearse, and regularly attends funerals and scrapyards – which drives his overbearing socialite mother (Vivian Pickles) up the wall. After psychologists and relatives fail to open him up to his emotions, Harold meets Maude (Ruth Gordon), a 79-year-old woman who also has a penchant for attending funerals. The spark of their odd friendship evolves into much more as the two find passion for life in each other, and as they find a love that few understand and even fewer accept, the whole journey is sublimely scored by Cat Stevens.

While it was released to severely divided opinions and a dismal box office, running mere days before being pulled from theaters, Harold and Maude has grown to be considered one of the best comedies of all time, and I couldn’t agree more with that assessment. Silly and sickly cynicism gives way to one of the most touching stories of love, loss, and the weight of memory that has yet been put to film, and it only gets more poignant and impactful with each rewatch.

While not the most obvious choice, it certainly remains one of the timeless ones.

Nathan Osborne – Love, Simon (2018)

It can be very tempting to ignore a film’s quality when you want it to celebrate its very existence. If you’re invested in a piece of art succeeding because you admire what it represents, you can often overlook flaws in its fabric. It’s happened time and time again and hell, I’m guilty of doing it myself. But here’s the thing about Greg Berlanti’s Love, Simon: it is a genuinely terrific film in its own right, and a defining romantic comedy at a moment we were beginning to question their relevance as the industry evolved.

As impressive as it is important, Love, Simon is a wildly enjoyable, emotionally stirring and captivating coming-of-age film that encompasses themes we have seen countless times before within the rom-com genre, but framed here in a new manner. In such crowd-pleasing fashion, Love, Simon uses the genre’s conventionality to normalise gay romance and stories in mainstream cinema: it doesn’t claim to reinvent the genre wheel, it simply charts a new, more inclusive course that makes the idea of love accessible to all audiences.

Even aside from its cultural significance, though, Love, Simon discovers the wonderful sweet spot between romance and comedy. In equal measures funny and heartwarming, the ratio is tightly perfected and delivered with so much emotion and warmth. Where some rom-coms can struggle to balance the two genres – flitting between them awkwardly – Love, Simon so confidently tows the line and infuses the two, resulting in a beautifully well-rounded piece that will make you laugh and smile as often as it makes you cry and swoon. Armed with Jack Antonoff’s impeccably curated soundtrack and a tremendous ensemble fantastically led by Nick Robinson, Love, Simon has everything going for it.

Those that damn the film’s conventionality and dismiss its adherence to the genre’s formula are overlooking its purpose and entirely missing the point: Love, Simon is heartfelt filmmaking bound to inspire and move many by normalizing a love story rarely seen in such unapologetically mainstream cinema. Love, Simon is one of the finest rom-coms ever made, smartly reconfiguring the conventionality of the genre to elicit a real change – it’s so damn entertaining in the meantime too.

George Nash – 13 Going on 30 (2004)

Life is packed full of wonderful, painful ironies. Perhaps the greatest of these comes when you’re 13. You’re blowing out the candles on your Caterpillar cake surrounded by your friends hoping that you’ll wake up tomorrow and be 30. Then, when the big 30 eventually does show up, and you’re nursing the mother of all hangovers by blowing a hot, greasy kebab surrounded by your friends, the only thing you’ll be truly wishing for is to be 13 again.

The second greatest irony of life is that 13 Going on 30 – a 2004 romantic comedy about time travel with an ingredients list that, by all rhyme and reason, should cook up the most sickly sweet, stomach-turning genre bake imaginable – is actually a beautiful, brilliantly bonkers film.

Blending nostalgia with a touching sentiment, one hip soundtrack, and Mark Ruffalo – all with a light sprinkle of cheddar on top – 13 Going on 30’s heart is firmly in the right place. Jennifer Garner admirably anchors this coming-of-age tale with a sugar rush energy and charming naivety, while Andy Serkis – who, in 2004, was hot off his scene-stealing performance as Gollum in Peter Jackson’s LotR trilogy – threatens to pinch the show as an eccentric magazine Editor-in-Chief.

Funny, sad and – now more than ever – poignantly pertinent, 13 Going on 30’s message about being yourself, following your heart (not the crowd) and choosing kind – as well as eating more sweets from your childhood – is one we could all use right about now.

But, hey, don’t just take our word for it. Ask Ariana Grande.

Maria Lattila – Crazy Rich Asians (2018)

I never knew I needed a wedding where the bride walks on water and the guests sit amidst some grass holding tiny little lights while a cover of Can’t Help Falling In Love plays in the background in my life. In fact, I’ll go as far as saying I’m not a romantic: I hate weddings, candle-lit dinners and I especially hate romantic comedies, with a passion. Sure, a few romantic films have passed my very, VERY strict standards and have become solid favourites, but let’s just say there aren’t a lot of romantic comedies in my collection.

And then Crazy Rich Asians happened. The story of an already successful girl connecting more profoundly with her own identity not only made this writer weep in public but also fall in love with a whole genre. Crazy Rich Asians doesn’t exactly reinvent the genre, just tweaks it to make it better, which is what every genre film should be doing. I found its unashamedly over-the-top romantic outlook and wildly excessive visual style hard to resist. It’s like someone took your generic romantic comedy and gave it some ecstasy and a new stylist.

What I love most about Crazy Rich Asians is the character of Rachel Chu. She kicks some serious butt, you guys. She is a professor living in New York, beating TAs in a game of poker, and that’s all before lunch. Here I am, stuffing my face with a pint of Ben & Jerry’s. The plot never requires her to change who she is; instead she strengthens her own sense of identity and self-worth. The beautiful man always feels like an added bonus, not the main goal. She’s the kind of person I hope to grow up to be one day; strong, independent, and confident, with or without a man.

Dave Fontana – It Happened One Night (1934)

It’s the quintessential love story that we’ve all heard time and time again: guy meets girl, guy and girl despise each other from the get-go, guy and girl get thrown into an unexpected situation that forces them to get to know one another, guy and girl unwittingly fall in love, but then have a brief falling out before, finally, settling down and living happily ever after (or so we hope).

Yet, back in 1934, such a frame for a romantic story on screen was just in its beginning stages, and Frank Capra‘s It Happened One Night paved the way for untold love stories to come. Soon thereafter, the screwball comedy emerged, resulting from the strict Motion Picture Production Code that had been set on the film industry, and here many elements of It Happened One Night can be seen. There is the basic rom-com structure, as mentioned above, here dealing with a rich heiress named Ellen “Ellie” Andrews (Claudette Colbert) who is on the run from her father in order to be with the excessively dull King Westley, and on the way gets caught up with reporter Peter Warne (Clark Gable), who decides to help Ellie in exchange for her story. Yet, in classic screwball fashion, it’s their whimsical adventures along the way that pave the way for their subsequent romance.

Here, to name just a few of my favorite scenes: the pretend husband and wife scene, in which Peter and Ellie have to create a believable dialogue of a married couple in order to throw off the authorities looking for her; the sly, know-it-all quotes from a never-better Clark Gable, in which he discusses the best methods of dunking a donut in coffee, undressing, and riding piggyback. And, of course, there is the hitchhiking scene, pictured above, in which Gable, while munching on a carrot, fastly discusses the top three methods of getting picked up, but is soon unseated by Ellie herself.

Above all, there is just something so sincere about It Happened One Night, from its pitch-perfect acting, to the nuanced direction by the legendary Frank Capra, to the unlikely yet still believable love story at its heart. Notably, it was also the first film to win the top five at the Academy Awards: Best Picture, Director, Screenplay, Actor, and Actress. To me, it’s one of the only films to fully deserve that commendation.

Zoe Crombie – Juno (2007)

Though more sensationally about teenage pregnancy, Juno is a hilarious film that touches on love and romantic relationships at all their stages. Despite the critical acclaim the movie received upon release, it remains somewhat controversial amongst viewers now for its stylised script that uses several layers of intentionally outdated slang and for its seemingly ambivalent attitude towards abortion (from both pro-choice and pro-life groups). This may rub some people the wrong way, but for me and I imagine many others, it is precisely these elements that give the film its distinct personality and its thought-provoking examination of a fully fleshed out female protagonist – both traits sadly lacking in many other romantic comedies.

Juno follows the precocious and rebellious Juno MacGuff (Ellen Page) in the nine months of her pregnancy, along with her quirky blue-collar family, timid boyfriend Paulie Bleaker (brought to life by the perfect casting of Michael Cera), and the wealthy family who intend to adopt her unborn child. This provides ample opportunity for looking at the relationships of various characters at different levels of maturity and for creating the often sweet humour that comes from these people trying to navigate life in wildly different ways. For me, the funniest moments come from the conversation between Juno’s blunt father Mac and the reserved, middle class Vanessa, who intends to adopt the baby – at one point Mac enquires about her Pilates machine, asking her ‘what you make with it’.

As a character-driven film, Juno excels in both its lighthearted humour and in its surprisingly deep and insightful dramatic moments. A film that can make me both laugh and cry in the same fifteen minute period, it is one of the greatest rom-coms in recent years, carrying the optimistic message that ‘the best thing you can do is find a person who accepts you for who you are’, whether that means accepting an interest in obscure horror films, an unusual love of tic-tacs, or the burden of a teenage pregnancy.

Owen Butler – La La Land (2016)

What can be said about Damien Chazelle‘s La La Land that hasn’t been already? Arguably one of the best original releases of the decade, it also takes the spot for my favorite film of all time, as I consider it both a masterpiece in its own right and the movie that truly kickstarted my deeper love for cinema.

Chazelle is undoubtedly one of the most meticulous directors of our time. Everything about La La Land is perfect, from the more surface-level aspects like the performances and music to the technical details like the cinematography, choreography, and editing. But what makes it different than other entries in the romance genre is the way it silently acknowledges the platitudes of its predecessors and abandons them in favor for a wholly unique and bittersweet ending that leaves me in tears every time I watch it.

The film is an embodiment of so many feelings, and yet it never feels too condensed for its own good. The plotting is perfect. The romance feels real. And in the end, so does the movie itself. Even throughout the fantastical elements of it, the way it concludes is so gripping and lifelike that it takes the romantics and cynics and brings them together in a celebration of the strengths of each other. There’s not a second that doesn’t feel utterly fascinating in execution, and it all adds up to one of the greatest romance films of all time.

Jo Bradley – 10 Things I Hate About You (1999)

This movie has everything you could want in a romantic comedy: a coming-of-age story, an intelligent, modern Shakespeare adaption, a foul-mouthed Julia Stiles, and, most importantly, a gorgeous, young Heath Ledger in his prime.

In a very witty adaption of Taming of the Shrew, Kristen Smith and Karen McCullah successfully transport Shakespeare’s tale of love, lies, and scheming to a 1990s American high school.

The Stratford sisters, pretty, popular Bianca (Larisa Oleynik) and tempestuous, intelligent Kat (Stiles), live under the rules of their strict, domineering father (Larry Miller), who rules that Bianca can’t date until Kat can. The problem: every boy at school is intimidated by Kat, and that is the way she likes it. Well, every boy except for bad boy Patrick (Ledger), who is paid to seduce Kat by Cameron (Joseph Gordon-Levitt), the new kid in love with Bianca. As these plots always go, fake love turns into real love, and there the troubles start…

This cast, undeniably the best part of the film, is full of comedic talent. Julia Stiles is in her element as the sharp-tongued Kat, while still managing to bring a vulnerability to her performance. Heath Ledger is dripping with charisma as the charming rebel who’s not afraid of Kat. His public serenade to Franki Valli’s “Can’t Take My Eyes Off You,” in front of the entire school (marching band included), still ranks as one of the best rom-com moments ever. Notable supporting performances include Allison Janney as the hilariously horny school counsellor, Gordon-Levitt as the likeable boy in love, Andrew Keegan as the hammy would-be model, and Miller as the pedantic overprotective father.

Smart, witty, and very, very funny, this rom-com is definitely one of the best.

Those are our favorite rom-coms. What are yours?