- There’s no better time for a rom-com binge than Valentine’s Day.
- For the day, we’ve created a comprehensive list of the 53 best romantic comedies ever made.
- The list includes gems like “When Harry Met Sally,” “The Proposal,” and “(500) Days of Summer.”
- Visit Insider’s homepage for more stories.
For most of the last decade, film critics spent a lot of their time writing about the so-called death of the romantic comedy.
And despite the popularity of these statements, they were always greatly overstated, sprinkled with tinges of misogyny, and half-baked â€” the genre has never really faltered in popularity or quality.
Now, this year, due to ongoing COVID-19-related travel restrictions, it is likely that most people will have nothing to do and nowhere to go on Valentine’s Day. Well, controversially, unless you’re in New York City. So, there’s really no better time to delve into the expansive history of romantic comedies.
Below, Insider’s entertainment team picked 53 of our favourite romantic comedies that will get you through the big day.
The list includes 80’s classics like “Moonstruck” as well as new gems like “To All the Boys I’ve Loved Before” and, of course, a whole bunch of Nora Ephron and Richard Curtis classics.
Keep reading to see which films made the cut, listed below in no particular order.
“When Harry Met Sally…” (1989)
Few rom-coms capture the absolute agony (and pure bliss) of realising that you’re in love with your best friend like “When Harry Met Sally.”
Starring Billy Crystal and Meg Ryan as the titular Harry and Sally, Rob Reiner’s 1989 classic gifted us with iconic lines (who could forget the hilarious reaction of the woman at Katz’s after Sally fakes an orgasm there during lunch with Harry?!) and a stellar cast (including the late Carrie Fisher in one of her best performances).
But at the core of the film is a tender, beautifully-explored love story, set against the backdrop of New York in the fall and winter.
While the costumes, script, and characters are flawless, overall, “When Harry Met Sally” is a gentle reminder that true love sometimes takes a while to find – but is always worth waiting for. – Libby Torres, entertainment reporter
I’m a sucker for a Jane Austen-inspired romantic comedy, so I consider “Clueless,” a 1995 film loosely based on “Emma,” to be one of the all-time greats.
Trading in the English countryside for the tree-lined streets of Beverly Hills, the cult classic follows a well-intentioned, wealthy high-school girl as she juggles classes, friendship, and the ongoing quest to pass her driver’s test. Blissfully unaware of boundaries, she can’t help but meddle in the personal lives of those around her.
While many romantic comedies from the ’90s haven’t held up, “Clueless” – with its iconic one-liners, stacked cast, and impeccable costuming – has aged with grace. – Claudia Willen, junior entertainment reporter
“Coming to America” (1988)
Eddie Murphy’s “Coming to America” is one of my earliest cinematic experiences. Alongside Alfred Hitchcock’s “The Birds,” it was one of the films that my parents believed I just “had” to see as a child.
Straight off the success of “Beverly Hill Cop 1 and 2,” “Trading Places,” and his comedy special “Raw,” Eddie Murphy stars as Prince Akeem, the sole heir of a fictional African country named Zamunda.
We meet Prince Akeem as he is about to tie the knot in an arranged marriage, but instead of going through with the ceremony, he decides to travel to New York to find a woman who will love him for his personality, not his money.
“Coming to America” was a huge worldwide box office hit taking home over $US250 million, and the film is still one of the most financially successful romantic comedies of all time. –Zac Ntim, junior entertainment reporter
“Four Weddings and a Funeral” (1994)
“Four Weddings and Funeral” is the classic rom-com. The movie launched Hugh Grant into super-stardom, winning him a BAFTA for best actor, and screenwriter Richard Curtis has gone on to be one of the best rom-com filmmakers of all time.
“Four Weddings” follows Grant as a super-awkward British bachelor who falls for an American woman over five different social occasions.
The movie is so good that it even smashed through the Academy Awards’ usually-stuffy pretensions, landing a best picture nomination despite rom-coms not often getting a look-in at the Oscars. – Jacob Sarkisian, entertainment reporter
“10 Things I Hate About You” (1999)
“10 Things I Hate About You” is a Shakespearean adaptation wrapped in quintessential late-1990s vibes, and it has everything I want in a movie: angsty teens, a dreamy cast, and a killer soundtrack.
Watching Julia Stiles break while she delivers her “I hate the way I don’t hate you. Not even close. Not even a little bit. Not even at all” line never fails to turn me into an emotional wreck.
And I forever have unrealistic romantic standards because I’ll never have Heath Ledger serenading me while dancing on a set of bleachers. – Fíona Clair, associate freelance editor
“Crazy, Stupid, Love” (2011)
“Crazy, Stupid, Love” has one of the best twists of any rom-com you’ll watch.
You head into this film thinking you’re getting a movie about a hotshot casanova (Gosling) acting as a wingman to an unhappy middle-aged man on the verge of divorce (Carrell).
Halfway through the movie, all hell breaks loose as the two learn an uncomfortable truth and it’s an incredible moment to watch.
Not only is the chemistry between Carrell and Gosling incredible, but Gosling and Emma Stone prove that they should continue making rom-coms until the end of time. (Don’t believe us? Just watch them dance in “La La Land”). – Kirsten Acuna, entertainment correspondent
“(500) Days of Summer” (2009)
At first, “(500) Days of Summer” may feel trite and condescending. A girl with effortless charm and baby-deer eyes who knows the words to The Smiths’ most popular song? How quirky and rare!
And sure, as a teenager, it was hard not to fall for Tom (Joseph Gordon-Levitt) and his creative, devoted, hopeless romantic ways.
But in reality, the film’s thesis is voiced by Tom’s cynical younger sister: “Just ’cause some cute girl likes the same bizarro crap you do, that doesn’t make her your soulmate.”
“(500) Days of Summer” actually condemns the very dynamic it presents – and, by extension, the brand of courtship you tend to see in most rom-coms. Tom’s love for Summer (Zooey Deschanel) isn’t just surface-level, but reductive, bordering on objectification. He sees her as a projection of his own desires.
The film’s overarching plot may not be deeply romantic, but it is instructive. It invites us to examine our own self-indulgent affections, and to see others as complex people.
In a disruption of the genre, Tom doesn’t end up with The Girl. But his mistakes are relatable enough to keep us rooting for him, and he grows enough to justify an optimistic future. –Callie Ahlgrim, music reporter
“The Big Sick” (2017)
Emily V. Gordon and Kumail Nanjiani’s based-on-a-true-story movie is one of the most moving, funny, and romantic films made in the last decade.
“The Big Sick” is surprising and heartfelt and the kind of story that makes you believe in love again. It will also make you laugh, and probably cry a bit along the way. – Kim Renfro, entertainment correspondent
“13 Going on 30” (2004)
“13 Going on 30” stars Jennifer Garner as Jenna Rink, who wakes up to find herself “30, flirty, and thriving” after making a wish on magic dust when her 13th birthday party goes awry.
Garner is delightful, sincere, and perfectly embodies Jenna’s awe at suddenly being an adult while simultaneously being child-like at heart. You can’t help but root for Jenna as she reconnects with her childhood crush (played by Mark Ruffalo) and navigates her job as a big-time magazine editor.
“The Proposal” (2009)
Sandra Bullock, Ryan Reynolds, and Betty White are an absolute comedic dream in this film. It follows a Canadian book editor (Bullock) in the US as she forces an engagement on her assistant (Reynolds) in order to avoid deportation.
The premise is a little bit dated and, really, nothing new (two people are forced together and end up falling in love), but somehow the movie feels timeless. Every actor brings plenty of heart and comedy to their roles. This is one of my go-to films on a bad day.
There’s really nothing like watching Bullock and White dance in the woods to “Get Low.” – Paige DiFiore, lifestyle and entertainmentfreelance editor
“Legally Blonde” (2001)
“Legally Blonde” starts off as a film about a sorority girl following her mediocre ex to Harvard Law School in an attempt to win him back, but it ultimately transforms into a story of a young woman who chooses to invest in herself and the equally underestimated women around her.
Reese Witherspoon is endearing as ever in the role of Elle Woods, as she scores a 179 on the LSAT, fights back against sexist stereotypes, teaches how to properly bend and snap, and solves a murder with an unparalleled knowledge of hair care.
And sure, in true rom-com form, she ends up in another relationship too, but the new guy doesn’t suck!
With a third movie currently set for release in May 2022, it’s clear this rom-com has withstood the test of time; it’s still just as fun, brilliant, and relevant 20 years later. (Cue Elle asking,“What, like it’s hard?”) – Courteney Larocca, celebrity and music editor
The teaming of Will Smith and Eva Mendes delivers one of the best rom-coms ever made.
Smith plays a guy who, years after a traumatic breakup, builds a unique defence mechanism to love: being a “date doctor” whose job it is to build lasting relationships. Mendes is a no-nonsense New York City gossip columnist who has no time for a relationship. The two fall for each other thanks to hilariously destructive dates.
Then there’s Kevin James along for the ride as one of Smith’s clients who wants to get a woman (Amber Balletta) out of his league.
Honestly, this movie has everything you want from a great rom-com. – Jason Guerrasio, senior entertainment reporter
“Mamma Mia” (2008)
The genius who decided to combine ABBA music and Meryl Streep in one showstopping hit deserves every Academy Award.
This jukebox musical – and its just-as-fun sequel – is the perfect movie for practically any occasion. Need a feel-good flick? Watch “Mamma Mia!” A wine night with your best friends? Watch “Mamma Mia!” Wanderlusting to move to a remote Greek island? Watch “Mamma Mia!”
With a stellar cast and soundtrack to boot, this musical rom-com has all the camp, but also sports all the heart – I have never not sobbed when Streep and Amanda Seyfried sing “Slipping Through My Fingers.” – Crystal Wall, lifestyle and entertainment freelance fellow
“Bring It On” (2000)
There are many reasons why “Bring it On” remains iconic to this day, and Gabrielle Union is at the top of that list.
But we also cannot forget the rom-com perfection that was Kirsten Dunst and Jesse Bradford’s characters brushing their teeth side-by-side and giving a masterclass in silent flirtation. –Kim Renfro
“Say Anything…” (1989)
“Say Anything” is so much more than its signature boom-box scene – though it does summarize the film’s quiet, rosy, irresistible sincerity.
Despite its shortfalls – including a too-sudden dramatic twist and some lacklustre dialogue – the central characters make such a convincing, stupidly sweet couple that it’s impossible not to swoon when they finally kiss in the car.
John Cusack plays Lloyd as soft but not wimpy, while Ione Skye’s valedictorian Diane is sweet and sheltered without seeming too naive. He’s uber-attentive, willing to lay his heart down as collateral, while she’s cautious and doesn’t feel truly known by any of her peers.
They make an odd couple on paper, but there’s nothing quite like clumsy outcast love. – Callie Ahlgrim
“How to Lose a Guy in 10 Days” (2003)
Although I don’t condone the blatant disregard of journalistic ethics at the centre of “How to Lose a Guy in 10 Days,” Kate Hudson and Matthew McConaughey’s chemistry is next level.
Not only is the plot the ultimate, trope-y – admittedly, sometimes to a fault – battle of the sexes, but it also has a great mix of cliché, heartfelt, and genuinely funny scenes.
When I watched Hudson step out of the car in her yellow, backless dress as a 10-year-old, I thought it was the pinnacle of movie fashion, and I’d stand by that today. – Fíona Clair
“She’s the Man” (2006)
This movie is probably the reason half the world first began crushing on Channing Tatum, and then the other half caught on when “Step Up” premiered later that year.
It’s also a fantastic reminder of the amazing physicality Amanda Bynes brought to her comedy.
The whole movie does hinge on outdated assumptions about gender-identity and how it’s linked to physical appearance, so fair warning to those who haven’t rewatched it since the early ’00s. – Kim Renfro
“About Time” (2013)
“About Time” is one of Richard Curtis’ least favourably received films.
Upon its release, critics regarded it familial, conservative, and plot-hole-ridden. Now, despite this being the reason why so many of Curtis’ films are enjoyable in the first place, there are some very good arguments to be made about the toxic, manipulative nature of the film’s narrative.
The movie follows a young man who discovers that the men of his family have the secret ability to travel back in time, and he uses this power to engineer favourable romantic encounters with women.
However, for many years, “About Time” was a favourite among Britain’s terrestrial television networks. The film would play over and over again as if ritual. So, by sheer indoctrination, it is my favourite Richard Curtis film.
Rachel McAdams is good too, as always. – Zac Ntim
“Someone Great” (2019)
If you’ve been dumped, you probably know that something as small as a song lyric can trigger a painful highlight reel of the past. In “Someone Great,” director Jennifer Kaylin Robinson examines the 24-hours following an unanticipated breakup, using music and flashbacks to piece together a mosaic of the 9-year relationship preceding it.
The Netflix original film is honest, relatable, and will probably tempt you to text your ex, but it serves as a healthy reminder that some things aren’t meant to last forever. – Claudia Willen
“Definitely, Maybe” (2008)
Yes, “The Proposal” is Ryan Reynolds’ classic, but the year before, the actor starred in a rather sweet rom-com where he recounts to his daughter, Maya (an adorable Abigail Breslin), how he met her mum.
Instead of delivering a straight-forward story, he tells Maya about three different past loves, changing up their names, so she can guess her mum.
The film leaves you guessing the identity of Maya’s mother right along with her until its end.
Within that tale is a complex, unfinished love story that Maya helps make a reality by the film’s end. It’s a love story, but also a feel-good father/daughter film. – Kirsten Acuna
“Love, Simon” (2018)
What’s not to love about “Love, Simon?” The simultaneous coming-of-age and coming-out movie challenges the idea of heterosexuality being the default (there are even satirical scenes in which Simon’s straight friends similarly muster up the courage to “come out” to their parents).
The film is all about love being love and, as a queer biracial woman, I appreciate the wholesome representation of interracial couples in it.
It reaches its peak (figuratively and literally) at the top of a Ferris wheel, where Simon and his once-secret admirer share their first kiss.
It also boasts a superb soundtrack, which ranges from Brenton Wood’s “The Oogum Boogum Song” to Bleachers’ “Wild Dreams.”–Ashley Simone Johnson, celebrity and music fellow
Cher and Nicolas Cage, who play star-crossed lovers Loretta Castorini and Ronny Cammarieri, are the grounding force of this film, which is one of the funniest romantic movies ever made.
While their love story is filled with yearning, the headstrong nature of both characters (and their idiosyncratic Brooklyn Italian families) leads to some pretty hilarious moments – including Ronny wailing in the basement of the bakery where he works that he lost both his “hand” and his “bride” because of an accident with a bread slicer, and Loretta later slapping him across the face and telling him to “Snap out of it!” after he proclaims his love for her.
There’s also plenty of tender moments between the two, however, including a romantic night at the Metropolitan Opera.
I love “Moonstruck” for many reasons, but the inimitable performances of Cher and Cage – and the undeniable spark between their characters – definitely make this a standout romantic comedy. – Libby Torres
“Set It Up” (2018)
Netflix’s “Set It Up” is in many ways formulaic – for starters, it takes place in one of the most popular rom-com destinations, New York City – but still manages to feel like a fresh take on the genre.
The film stars Zoey Deutch as a 25-year-old assistant named Harper, whose journalism skills are underused because she’s too preoccupied with being an assistant for a tough boss, editor Kirsten Stevens (Lucy Liu).
To free up her schedule and focus on things that are far more important than fetching Kirsten’s kale salads at late hours, Harper concocts a plan with an equally dissatisfied 28-year-old assistant named Charlie (Glen Powell) – who answers to a demanding, rich boss named Rick Otis (Taye Diggs).
In setting up their bosses so they can be free, Harper and Charlie realise they just might be an imperfect match for each other, and Deutch and Powell make an entertaining duo. –Olivia Singh
Naturally, a large part of my attachment to “Aquamarine” is nostalgic.
I remember being 10 years old and watching the movie in a pillow fort with my friends: pining after Raymond (Jake McDorman) perhaps cinema’s only hot lifeguard who’s equally sweet and compassionate; dreaming about nails that change colour with your mood; whispering compliments into each other’s ears like the starfish earrings.
But those kinds of memories, that vision of cherished sisterhood, is precisely what the story engenders.
“Aquamarine” is a rom-com insofar as it tells a boy-meets-girl story – but the deeper, more honest love between its young female leads is the film’s true emotional core. – Callie Ahlgrim
“Sydney White” (2007)
I’m a huge fan of cheesy adaptations, and “Sydney White” may just be the cheesiest of them all.
A late-2000s retelling of “Snow White” through the lens of the collegiate Greek system might not sound like a hit on paper, but the talented cast made this a rom-com to remember.
Sara Paxton was an incredible rom-com villain, Amanda Bynes was a perfectly believable down-to-earth heroine, and the “seven dorks” gave the film plenty of heart. – Fíona Clair
“The Wedding Singer” (1998)
With just the right combination of cynicism and romance and the garish ’80s music-focused setting, “The Wedding Singer” delivers basically everything you’d want in a rom-com.
Adam Sandler and Drew Barrymore are a fantastic on-screen couple, delivering the kind of performance that really makes you believe these two characters fell in love over the course of a brief montage.
And of course, we can’t forget that “Somebody Kill Me” is an Adam Sandler jam. – Kim Renfro
“The Princess Bride” (1997)
“The Princess Bride” is the textbook example of “inconceivably” good storytelling.
Whenever I want a moment – or an hour and 38 minutes – of escape, I dive into the world of complexly straightforward characters, quotable sequences, and a love story that pierces my cynicism.
These days, it seems like no arc feels more satisfying than “good triumphs evil.” So, paired with seat-gripping fencing scenes and campy swamp monsters, this film epitomizes the best of what the fantasy genre has to offer. – Crystal Wall
“What a Girl Wants” (2003)
As a child of divorce, I appreciate “What a Girl Wants.” As someone who now expects to go to London and meet the punky, cheeky guy of my dreams, I blame it for my romantic problems.
From Colin Firth absolutely rocking out in skintight leather pants to Amanda Bynes leading a dozing party crowd in a dance to “Get Up Offa That Thing” – a scene that curiously came out a year before the iconic “Thriller” sequence in “13 Going on 30,” make of that what you will – so much of this film lives rent-free in my mind 18 years later. – Fíona Clair
“To All the Boys I’ve Loved Before” (2018)
Netflix revived the rom-com genre for a new generation with the 2018 movie “To All the Boys I’ve Loved Before,” based on Jenny Han’s best-selling book series of the same name.
The film centres on high schooler Lara Jean Song Covey (Lana Condor), who enjoys stress-baking, watching romantic movies, and daydreaming about love. Her life spirals out of control when her mischievous little sister secretly mails love letters that Lara Jean addressed to five of her childhood crushes.
Then, she enters a fake relationship with jock Peter Kavinsky (Noah Centineo) and, in true rom-com fashion, develops feelings for him.
Condor and Centineo’s chemistry is of-the-charts in the film (and its two sequels) and “TATB” has all the ingredients for a perfect modern-day rom-com.
The movie is a much-needed dose of representation in the rom-com genre, effortlessly exploring Lara Jean’s coming-of-age story while weaving in her identity as an Asian American. –Olivia Singh
“You’ve Got Mail” (1998)
Another Nora Ephron classic, part of the charm of “You’ve Got Mail” lies in the fact that it would most certainly not happen today.
Tom Hanks and Meg Ryan play rival bookstore owners – Hanks’ Joe Fox works for Fox Books, a chain of corporate bookstores a là Barnes & Noble, and Ryan’s Kathleen Kelly is the owner of an adorable independent bookstore on the Upper West Side – who meet online and begin corresponding via email, their true identities a mystery to one another.
It’s quaint and slightly funny to see Joe and Kathleen’s romance blossom via AOL, especially considering the prevalence of dating apps today.
But as we continue to rely on technology and virtual connections to keep us sane during the coronavirus pandemic, “You’ve Got Mail” is a charming reminder of how online relationships can be just as fulfilling as real-life ones. – Libby Torres
“John Tucker Must Die” 2006
There may not have been a movie that 11-year-old me loved more than “John Tucker Must Die.” There is just something so deeply satisfying about four teenage girls teaming up to get revenge on the high school jock who outwardly lies about his relationship status to sneakily get away with cheating on all of his girlfriends.
Equally entertaining are all the ways John Tucker (Jesse Metcalfe) finagles his way out of the girls’ pranks, casting him in the same light as a male Regina George. But instead of coloured bras under snipped tank tops, it’s bright thongs under basketball shorts.
Also, Brittany Snow is adorable as Kate, and Penn Badgley is in it as the Other Tucker. You know it’s gotta be good when Badgley stars as the sweet love interest the lead character ends up with at the end. – Courteney Larocca
“A Knight’s Tale” (2001)
“A Knight’s Tale” is a seriously underrated movie with a hell of a cast – featuring Heath Ledger as the rom-com lead, Paul Bettany as Geoffrey Chaucer, and “Game of Thrones” star Mark Addy.
Ledger stars as a peasant who passes himself off as a knight in a bid for fortune and glory, but ends up falling for Shannyn Sossamon’s Jocelyn along the way.
Bettany is the pick of the bunch in this anachronistic medieval rom-com that combines jousting, chivalry, mischief, and David Bowie. – Jacob Sarkisian
“The Holiday” (2006)
“The Holiday” has an effect on me somewhere between a hot chocolate and a tranquilizer dart – it is indefinably soothing.
It’s syrupy, it’s glossy, it has Jack Black. The movie’s success comes in its absurdity – a quality that every good rom-com should have in spades – the dumb premise, the timeline that doesn’t really work, the driver who can’t drop Cameron Diaz off at the cottage forcing her to trek through the snow but then later somehow picks her up outside it.
The world is full of boring practicalities inhibiting pretty much anything in “The Holiday” actually happening – that’s why it’s brilliant.
Succumb to Nancy Meyers, succumb to “The Holiday,” let it wash over you like mulled wine. – Tom Murray, entertainment editor
“Palm Springs” (2020)
I hate time loop movies, which is a testament to just how good “Palm Springs” is.
The film follows two wedding guests (Andy Samberg and Cristin Milioti) as they’re forced to repeat the same day over and over. Filled with vibrant visuals, the film is also packed with humour and cleverness with a sprinkle of camp and a romance that feels refreshingly genuine.
It’s not love at first, second, or even fifth sight for the leads and it makes the ending even more satisfying.
And it’s just flat-out delightful having well-cast leading characters who are both intelligent, witty, and a little bit broken. – Paige DiFiore
I love a good wedding. It can be the ultimate gesture of love. And this star-studded cast engaged the audience even more by showcasing its ultimate sense of humour.
The women-powered cast was filled with the likes of Maya Rudolph, Kristen Wiig, Melissa McCarthy, Ellie Kemper, Rebel Wilson, and Wendi McLendon-Covey. But make no mistake – this movie isn’t a chick flick.
From Kristen Wiig’s tripping out on “relaxation pills” on a plane, to the bridal party’s food poisoning fiasco at the dress fitting, this movie is wildly chaotic – which is exactly the kind of content I like subscribing to. – Ashley Simone Johnson
“Sweet Home Alabama” (2002)
Why did Reese Witherspoon ever stop starring in romantic comedies? “Sweet Home Alabama” takes the enemies-to-lovers trope and adds in the irresistibly romantic childhood-sweetheart backstory.
There is a ‘my dad is a Confederate soldier reenactor’ subplot we’d like to jettison into the sun, but other than that this movie is a must-watch. – Kim Renfro
“Can’t Buy My Love” (1987)
Patrick Dempsey is great as a nerdy Arizona high schooler who suddenly becomes cool thanks to the help of his next-door neighbour, the popular cheerleader played by Amanda Peterson.
And no, she’s not doing it out of the kindness of her heart. Dempsey’s character pays her with the money he’s saved up from mowing lawns over the summer.
Before you know it he’s popular and the two fall for each other leading to a fun conclusion where they both ride off on his lawnmower into the sunset. (Yes, this movie is very 1980s.) –Jason Guerrasio
“Crazy Rich Asians” (2018)
The first time I watched “Crazy Rich Asians” in theatres in 2018, I loved it so much that I debated buying a ticket for the next showing.
Adapted from Kevin Kwan’s best-selling novel, the movie focuses on a Chinese-American economics professor that travels to Singapore to meet her boyfriend’s ultra-wealthy family.
The sizzling food at the Singaporean market, the high-fashion outfits paired with exorbitantly expensive jewellery, and the gorgeous wedding scene set to Kina Grannis’ version of “Can’t Help Falling in Love” are each reason enough to watch “Crazy Rich Asians.”
But what really elevates the film, which features a star-studded all-Asian cast, is its ability to tackle complex issues like class, tradition, and immigration within the context of a romantic comedy. – Claudia Willen
“Just My Luck” (2006)
For being a fantasy love story between Chris Pine (the best Chris, in my opinion) and Lindsay Lohan set to the music of iconic British boy band McFly, “Just My Luck” is incredibly underrated. It has a little bit of mystery, a stellar cast, and plenty of physical and situational humour.
“Bend It Like Beckham” (2002)
Gurinder Chadha is one of the UK’s most interesting writer-directors.
Her breakout movie, “Bend It Like Beckham,” harnessed the power of the English national game to make a persuasive, compassionate, and hilarious case for multiculturalism in contemporary British society.
The movie follows Jess (Parminder Nagra), who joins a local soccer team against the direct rules of her conservative Sikh parents. And Jess deploys elaborate excuses to hide her soccer games from her family as well as her romance with her coach, Joe.
Chadha has always been fascinated by dual identities and diaspora. But unlike her later films, which often veer into shaky territory, “Beckham” is uniquely biting and unflinching in its depictions, all of which remain alarmingly relevant today. –Zac Ntim
“Knocked Up” (2007)
Judd Apatow wrote and directed this comedy that would push Seth Rogen to superstardom.
Rogen plays a guy who learns the woman (Katherine Heigl) he had a one-night stand with is pregnant. He decides to be alongside her as she goes through the pregnancy, leading to some funny situations between the two as they try to build a relationship despite being total opposites. – Jason Guerrasio
“Notting Hill” (1999)
“Notting Hill” does to London what Netflix’s “Emily in Paris” does to the French capital. And one might argue to an even greater degree. The romanticization of the city is a complete and wild fabrication – at least Lily Collins and co. are based on outdated stereotypes.
But this is precisely why “Notting Hill” is one of the greatest romantic comedies ever made.
The film’s writer Richard Curtis is able to make the idea of a random romance between a moody British book shop owner (Hugh Grant) and an American movie star (Julia Roberts) a relatable and enviable proposition.
“Notting Hill” is simply movie gold. – Zac Ntim
“50 First Dates” (2004)
There’s something about the chemistry between Drew Barrymore and Adam Sandler that’s very satisfying to watch.
After “The Wedding Singer,” the duo’s 2004 on-screen reunion became a favourite of mine in high school as Henry (Sandler) pursued a crush on Lucy (Barrymore), a young woman with short-term memory loss, despite knowing she would likely forget him the next day.
A guy who goes out of his way to try and get a girl to fall in love with him over and over again? Everyone wants to believe someone would put that much effort into a relationship.
It doesn’t completely hold up over a decade later because of some crude humour. Still, it’s particularly endearing to watch the montage of Henry trying to win over Lucy day after day and then find a solution so she’s not living in an eternal “Groundhog’s Day.”
The film also has a pretty solid Valentine’s Day soundtrack with “Friday I’m in Love,” “Hold Me Now,” “Every Breath You Take,” and Israel Kamakawiwo’ole’s excellent cover of “Somewhere Over the Rainbow.” – Kirsten Acuna
This one may be a semi-controversial addition to this list because sure, yeah, it wasn’t marketed as a comedy.
But I dare you to watch this film and not laugh at Robert Pattinson gritting his teeth as Edward Cullen and growling “This is the skin of a killer, Bella” while CGI gives the illusion that he’s sparkling in the sun.
Or when he looks constipated in science class as he glares at Bella (Kristen Stewart) with disgust as he holds back from draining her blood on the spot.
Or when Nikki Reed’s Rosalie watches Emmett (Kellan Lutz) playing vampire baseball and casually utters “my monkey man” like that’s a totally normal thing to say. Honestly, the list is endless.
Regardless of its indie-drama origins, “Twilight” has a clear comedic component to it and there’s obviously a romance involved too. So yes, “Twilight” is one of my favourite romantic comedies, thank you very much. – Courteney Larocca
“Easy A” (2010)
Emma Stone’s star was already rising in Hollywood when “Easy A” was released, but the 2010 film took her career to new heights.
Stone nails her performance as Olive Penderghast, who comes clean (via a webcast, because this was before the days of social media livestreams) about the events that took her from a wallflower to the most gossiped-about teen at Ojai North High School.
“Gossip Girl” alum Penn Badgley is endearing as Olive’s love interest Todd, while Stanley Tucci and Patricia Clarkson are scene-stealers as her quirky parents.
And if Nathaniel Hawthorne’s “The Scarlet Letter” was required reading for you in high school, then you’re likely to enjoy its influence on “Easy A.” – Olivia Singh
“Just Friends” (2005)
Reynolds is completely hilarious in this comedy that focuses on the terrors of being in the “friend zone.”
After spending most of his youth as the overweight friend to his crush Jamie (Amy Smart), Chris (Reynolds) grows up to be a successful and attractive music executive who has no problem getting the ladies.
But after returning to his hometown, he gets another chance with Jamie and proves to her he can be more than a friend.
His awful way of going about doing it leads to some great slapstick comedy. – Jason Guerrasio
“Angus, Thongs and Perfect Snogging” (2008)
Besides learning British slang and getting lost in the cast’s accents, I was cringing at almost all of 14-year-old Georgia’s romantic encounters – and I loved every minute of it.
While it’s been a while since I’ve been a teenager, I could relate to the edgy measures the main character would take to get the rock star of her dreams to notice her. I supported her all the way through the “cheese puff orange” spray tan and horribly bleached hair.
Plus, by the end of the movie, Georgia’s dream boy wrote and performed a song about her, which just left me thinking: How do I get someone to write a song about me?– Ashley Simone Johnson
“What Happens in Vegas” (2008)
“What Happens in Vegas” came out more than a decade ago and I still quote a variety of its lines on a regular basis. Cameron Diaz’s gleeful voice yelling “SMOOTHIES!” pops into my head at least once a week.
This is just one of those movies that has no right to be so fun and funny, but somehow burrowed its way into my subconscious and shaped my sense of humour.
The unlikely pairing of uptight Diaz and playboy Ashton Kutcher just works – especially when the former is hurling oranges at the latter in the middle of the street – and the ridiculous repartee between their best friends (Lake Bell and Rob Corddry) injects crackle and fizz into even the most predictable scenes. –Callie Ahlgrim
“Pretty in Pink” (1986)
One of the John Hughes-written classics from the 1980s, Molly Ringwald plays Andie, who suddenly begins to date Blane (Andrew McCarthy). The problem is she’s poor and he’s rich, so they are operating in very different cliques.
With a tone that’s more adult than most of the high school-focused love stories of its time, this movie has stood the test of time thanks to its authenticity – and the classic song at the end, “If You Leave.”– Jason Guerrasio
“Nick & Norah’s Infinite Playlist” (2008)
I’m a sucker for New York rom-coms, and while “Nick & Norah’s Infinite Playlist” is a somewhat more recent addition to the genre, it perfectly captures the feeling of being young and in love in the best city ever.
The entire movie takes place during one chaotic night as aspiring musician Nick (Michael Cera) teams up with Norah (Kat Dennings) to track down a mysterious band who’s playing a show somewhere in the city.
The soundtrack is a perfect mix of late 2000s indie rock, and while Nick and Norah seem like an odd couple at first, by the end of the movie, you’ll be rooting for them.
With reverent portrayals of New York institutions like Veselka and Arlene’s Grocery, “Nick & Norah’s Infinite Playlist” is both a love letter to the city and to young love itself. –Libby Torres
“Chungking Express” (1994)
Wong Kar-wai is often described as the rock star of Hong Kong cinema and his third film, “Chungking Express,” is perhaps the best example of this.
The movie, which was conceived, shot, and edited within six weeks, is a chaotic hybrid that remains one of the defining works of 1990s cinema.
At its core, “Chungking Express” is a classic rom-com about the pain and joy of falling in love, but its narrative is split into two intersecting stories, both set in Hong Kong and centering on two love-struck police officers who mull around the city at night.
Like most of Wong Kar-wai’s other movies, distribution issues such as poor translation have made his work difficult to access outside of Asia, but Criterion just released a new 4K restoration of the director’s most acclaimed works, including the dizzying “Chungking Express.” – Zac Ntim
“Forgetting Sarah Marshall” (2008)
Of all the Judd-Apatow crew movies, “Forgetting Sarah Marshall” stands a smidge above the rest.
Jason Segel is a charming doof, and Mila Kunis is a swoon-worthy love interest. Add in Bill Hader, Kristen Bell, and a vampire musical written during a depressive episode and you’ve got rom-com movie magic. – Kim Renfro
“Wedding Crashers” (2005)
“Wedding Crashers” is Vince Vaughn and Owen Wilson at their very best.
The 2005 rom-com follows two divorce mediators who routinely infiltrate weddings to seduce women. Their plans go awry, however, when one of them develops genuine feelings for a maid-of-honour named Claire (Rachel McAdams), who is already in a relationship.
As the duo accompanies Claire and her family to their preppy coastal home under false pretenses, they prove just how far they will go for love. – Claudia Willen
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