The general rule of thumb when it comes to romantic comedies is that they’re something a site such as this should steer clear of. However, there’s not one of you out there that’s never watched a romantic comedy, and we’d happily wager that there’s not one of you out there who won’t ever watch one again.
Here, then, for your delectation, is a collection of rom-coms from the past 30 years that won’t leave your brain seeping clever juice as you watch them…
10 Things I Hate About You
Many teen movies have a romantic comedy heart to them, and in the case of the excellent 10 Things I Hate About You, it has foundations of Shakespeare too. Based around the Bard’s The Taming Of The Shrew, it pairs the late Heath Ledger with the always-brilliant Julia Stiles, in a delightful movie. Joseph Gordon-Levitt is in the mix too.
There’s a lot of talent here, and it’s mixed together strongly.
(500) Days Of Summer
Before he was snared by the studio system for The Amazing Spider-Man films, Marc Webb developed (500) Days Of Summer “in a laboratory with my friend.” He takes the guts of the romantic comedy genre, and plays with chronology, mixes in music, and tells an otherwise fairly straightforward tale in an offbeat and diverting way. Zooey Deschanel is great too, as she tends to be.
The American President
The second union of writer Aaron Sorkin and director Rob Reiner, after A Few Good Men, is their best. What’s more, The American President serves as added interest for effectively being a dry run for The West Wing, given that it features the same kind of character set up, the walk and talk dynamic, and, crucially, Martin Sheen.
Sheen is in a supporting role here, as he was originally intended to be in The West Wing, and it’s Michael Douglas’ President Andrew Marshall who’s centre stage (Robert Redford had been linked with the part at one stage). Joined by Annette Bening, as a lobbyist whose politics bring her into sharp contrast with said President, Sorkin and Reiner fashion a funny, enjoyable and grown-up romantic comedy, with an ensemble cast rich in quality (Michael J Fox’s AJ, for a start).
It still holds up, too, and Douglas and Benning make for an unusual yet rewarding central pairing. Heck, you actually end up rooting for them. Fair play, Aaron.
As Good As It Gets
Jack Nicholson has proven more than once that the romantic comedy absolutely isn’t the domain of twentysomethings – check out Something’s Gotta Give for further evidence of that – but never moreso than we his Oscar-winning turn in As Good As It Gets. James L. Brooks’s film also secured a deserved Oscar for Helen Hunt, and if you’re looking for a reason why it works, take a look at the sequence where Nicholson’s often quite unpleasant character has to come up with a compliment for Hunt’s. It’s wonderful writing, wonderful acting, and wonderful directing.
Benny And Joon
Jeremiah Chechik’s film directing career was all but permanently derailed by The Avengers (not that one), and that’s a pity. Dig back just a few years before, and his quirky (in a good way) romantic comedy Benny And Joon was something of a treat.
Johnny Depp is excellent in particular as Benny, an introvert who nonetheless finds solace in practicing the physical comedy of Buster Keaton and Charlie Chaplin. Joon, played by Mary Stuart Masterson, has a mental illness and a protective brother. Yet Benny and Joon find kindred spirits in themselves, that Chechik’s film delicately, and entertainingly, explores.
Here’s a nice surprise. Definitely, Maybe follows Ryan Reynolds‘ character, who is telling the story of his romantic life to his young daughter. If you can get past that conceit – for it centers on where said daughter’s mother fits in – then this is quite a charming movie.
Reynolds in particular makes an affable lead, a man whose made his mistakes, but made them relatively innocently. The film is stocked well with decent side performances too, not least a heavily-drinking Kevin Kline, and smart turns from Elizabeth Banks, Rachel Weisz and Isla Fisher. Lightly funny, but generally warm, Definitely, Maybe is worthy of a blind punt.
Down With Love
Peyton Reed would go on to become the man in the Ant-Man bunker, ready to deflect flack for not being Edgar Wright. Yet his resume has some impressive, pre-Ant-Man films on it, and there’s a place in our heart for his stylish rom-com, Down With Love.
It stars Ewan McGregor and Renee Zellweger as the leading couple in a film that pays homage in style and tone to 1960s American comedies. Granted, it’s not as good as quite a few 1960s American comedies, but there’s a real love for what they’re doing here that sells the film even in its weaker spots. It’s got bags of charm too. We like charm.
Told mainly in flashback, Billy Crystal’s Forget Paris got fairly sniffy notices when it was first released, but we maintain it’s a better movie than it ever got credit for. Crystal himself takes one of the leads and Debra Winger has the other. A la When Harry Met Sally, it’s a story told over time about a couple who keep heading together before they’re pushed apart. What’s more, it’s set around the world of basketball, and stuffed full of cameos that’ll make little to no sense for those who don’t follow the NBA. Gently funny, Crystal is an underrated director (take a look at *61 for further evidence of that), and Forget Paris deserves a good audience.
This was the film that was supposed to turn Gerard Depardieu into a big American movie star. By this time, regarded as one of the best screen actors in the world, Depardieu was paired up with Andie MacDowell for Peter Weir’s film about a man trying to get a green card to stay in the United States. MacDowell is trying to help him, and naturally, they don’t get on. For quite a long time, as it happens.
Weir lets this play out with a laser-focus on keeping mawkishness out of his film. And like the best modern romantic comedies, he makes sure that there are two adults at the heart of this one, in this case thrown together for actually believable reasons. That in itself is the exception rather than the norm in the rom-com genre…
How To Lose A Guy In 10 Days
It’s a pretty crap film, but it’s worth it for the Celine Dion joke.
In Good Company
A film that was criticised by its star, Topher Grace, inside minutes of Steven Soderbergh’s Ocean’s 12 (“I totally phoned in that Dennis Quaid movie”), In Good Company is actually a really rather good rom-com. We don’t talk about The Quaid enough on this site, and we really should: he plays a man trying to hold onto his job here, whose boss – Grace – is basically nearly half his age. Oh, and falling for his daughter, played by Scarlett Johansson.
It’s a romantic comedy laced with something just a tad deeper here – the whole idea of an older generation being disposed of. And it’s from Paul Weitz, who also directed About A Boy, that would have gone on this list, had there been any real way to justify it as a rom-com. It’s still an excellent film, though.
Like you didn’t know this one was coming. The romantic angle may not be the first reason that many cite Harold Ramis’s Groundhog Day as a modern classic, but it’s actually the concrete on which the film is built. Bill Murray’s Phil Connors’ day of purgatory can only, ultimately, be escaped when he can find the way to Andie MacDowell’s heart (well, there’s more to it than that, but that’s a crucial part of the jigsaw). The song “I Got You Babe” is heard several times while he works all this out.
Gloriously written – and it’s worth digging out screenwriter Danny Rubins’ book on the development of the script – they’ll be talking about Groundhog Day in 50 years’ time. Over and over again, ironically.
Reportedly infamously inspired by a memo written by Jeffrey Katzenberg – that we looked at in more detail here – Jerry Maguire is a corking piece of cinema.
Written and directed by Cameron Crowe, the film has lots of ingredients that just shouldn’t work. But it’s a skilful piece of filmmaking here, with a terrific supporting turn by Cuba Gooding Jr. generating many, many laughs. Heck, there’s even a little kid in it who, rather than getting on your nerves, you end up wanting more screen time for.
Yet it’s Tom Cruise, in perhaps his best and most likeable leading man performance, who is the core of the movie. Granted, the film follows the template of the Tom Cruise movie – as gloriously recognised in the Rich Hall skit that we’re about to show you – but that doesn’t make this one any the worse. Plus, there’s a great breakthrough role for Renee Zellweger, pre-Bridget Jones too.
Keeping The Faith
A really, really, really good movie. To date, Keeping The Faith is the only movie that Edward Norton has directed, and he pulls together a cast that includes himself, Ben Stiller and Anne Bancroft.
The setup is unusual. It’s a love triangle, with two men falling for the same woman. The twist here is that one man is a priest, and one man is a rabbi. That in itself adds complications.
Norton, however, wrangles the material brilliantly (served by a strong screenplay from Stuart Blumberg). It’s a funny film he delivers, and deals with faith and romance in a manner that won’t have you reaching for the remote.
Kissing Jessica Stein
Sold, somewhat inevitably, as a romantic comedy that has a lesbian relationship at the core of it, Kissing Jessica Stein is a really tender, intelligent piece of work. It stars Jennifer Westfeldt in the leading role, one who’s on the lookout for her dream man. The film takes one or two unusual turns though – signposted to a degree by the marketing – and she finds herself drawn to female companionship rather than male.
Tightly written, Kissing Jessica Stein is an American indie gem, one that remains strong for a quiet, romantic night in.
Life After Beth
The most recent entry on this list, this one sees Aubrey Plaza as Beth, the girlfriend of Dane DeHaan’s character. Actually, scratch that: she was the girlfriend, and then she dies. But, er, she’s popped out of her grave and come back as a zombie.
It’s not a conventional date night movie this, but Life After Beth gets to the point, finds a use for a big kitchen appliance that might just bring the house down, and confirms Aubrey Plaza as an actress with range, talent, and an eye for a good, off-beat project. More please.
Written by Steve Martin, in part as a love letter to the city of Los Angeles, this is an under the radar movie with a fair amount of wit, and both Martin and his then-wife Victoria Tennant on strong form. It’s actually directed by Mick Jackson, who would go on to make one of the biggest romance movies of the 1990s with The Bodyguard. But L.A. Story is by distance the better film, and Martin’s writing is one of its key assets. A talking road sign is another…
Still holds up, this one. Cher and Nicolas Cage might not be the most obvious pairing for a romantic comedy, but maybe that’s one of the reasons why Moonstruck works as well as it does. Cher picked up one of the movie’s clutch of Oscars, and she’s great. She plays a late 30s widow, who lives with her family, and is in a relationship with Danny Aiello’s character, Johnny. Enter stage left Johnny’s younger brother, played by Nicolas Cage, and things take, well, a turn or two.
Crackling with smart dialogue, and with excellent performances from Danny DeVito and Olympia Dukakis. Moonstruck is a genuinely strong rom-com. One that deserves not to be overlooked…
Much Ado About Nothing
We’re cheating. You can take Kenneth Branagh’s version of William Shakespeare’s Much Ado About Nothing, or you can take Joss Whedon’s. Either way, you’re in for a cracking time.
Amy Acker and Alexis Denisof take the lead in the latter, which was made in Whedon’s house. Branagh and Emma Thompson, meanwhile are at the heart of the 1993 version, which is set in sun-soaked Tuscany. Both have merits. Both casts deliver (ah, Nathan Fillion, we love thee). Both have excellent musical scores too. Both are, in truth, pretty great.
Music And Lyrics
Hugh Grant basically takes on the role of Andrew Ridgley in his second collaboration with director Marc Lawrence. The first, Two Weeks Notice, isn’t much cop. But this one’s good, assuming you buy into the central idea that Grant – who, er, can’t sing very well – is a former ’80s pop hero, living off his old image. Thank the lord for Drew Barrymore, who proves to be his muse, and also shows that when it comes to romantic comedies, she’s genuinely an actress to cherish. Music And Lyrics is better than it looks.
My Best Friend’s Wedding
This one veers far closer to the template romcom than many of this list, but again, it has a couple of things in its favour. Firstly, there’s a delicious nasty streak to Julia Roberts’ leading character, that sets her a good deal away from rubbish such as The Runaway Bride (where the key question seems to be how she likes her eggs). Here, her best friend – played by Dermot Mulroney – is marrying the seemingly perfect Kimmy (played, brilliantly, by Cameron Diaz). And with the help of the scene-stealing Rupert Everett, she wants her old friend to actually marry her – as they’d agreed back in their teens.
There are moments of mawkishness here, certainly, but Everett and Diaz in particular generate plenty of good laughs. And behind the camera, director P J Hogan – who made the surprisingly dark Muriel’s Wedding – isn’t afraid of exploring the less savoury antics of Roberts’ character. It’s got a good sing song in it too.
My Sassy Girl
Three important words: ignore the remake. Instead, seek out the 2001 South Korean original of My Sassy Girl, and you’ll be rewarded with one of the very best romantic comedies of the past 25 years.
Based around a series of stories that Ho-sik Kim posted online, that were then turned into a novel, My Sassy Girl is more a romantic comedy than anything else. That said, it does defy genre to a degree. But the story of a mysterious girl whose name we never learn, and the young man who meets her, and the complicated relationship that subsequently develops.
Cha Tae-hyun and Ji-hyun both put in remarkable performances, and the film really is offbeat, and quite brilliant.
Richard Curtis’ rule of comedy is that you need to get a good laugh inside ten minutes. He comfortably does that with Notting Hill, perhaps the pinnacle of his bumbling Hugh Grant boxset. He surrounds Grant with interesting characters too, primarily Rhys Ifans’s wonderful Spike, but also sets up a conceit that’s interesting: can a movie star fall in love with the person on the street?
It’s not in vogue to like stuff like Notting Hill, but Curtis’ writing is rich here, and director Roger Michell cuts through to the core of the story without wandering off into sentiment. Furthermore, you can tell this has been written for Grant, and it’s him at his most likeable, most British, and most funny. It won’t convert non-Grant and non-Curtis folk, but it’s a quality rom-com nonetheless.
Steve Martin’s take on Edmond Rostand’s Cyrano De Bergerac is a masterclass in screenwriting and performance. His performance as Fire Chief CD Bales is one of his very best, and the film manages to mix both romance and comedy, without shortchanging you on either.
In the title role is Daryl Hannah, and she’s someone that CD’s colleague, Chris, feels very strongly about. As such, Chris enlists CD’s help to come up with the words to woo Roxanne. It’s a clever idea, and Martin respects the source material, whilst putting a strong mid-80s twist (complete with cheesy music over the opening titles) on it. Furthermore, the scene where he stands, with his sizeable prosthetic hooter, and comes up with 20 insults aimed in his direction, is comedy gold.
Shaun Of The Dead
A film that started a genre – the, er, ‘rom com zom’ or ‘zom rom com’, depending on your preference – that still seems to be going. It’s tricky to categorize Shaun Of The Dead as a romantic comedy, perhaps, but then it’s a major part of the film. After all, the premise sees Shaun (played by Simon Pegg) trying to patch things up with his ex-girlfriend Liz (Kate Ashfield). That there just happens to be a zombie apocalypse going on in the middle of it is the price you pay.
You don’t need us to sell Shaun Of The Dead to you, we suspect. Just don’t overlook its rom-com themes when it comes time to pick a romantic comedy off the shelf…
There’s almost a Doctor Who idea at the heart of Peter Hewitt’s Sliding Doors, a film based on the premise of ‘what if.’ In this instance, what if Gwyneth Paltrow’s character had taken a different turn at the start of her day? The film follows both eventualities, knitting them together surprisingly well. Never overburdened by its central idea and the potential complications it could involve, Sliding Doors was a surprise hit in the 1990s, but a deserved one. It’s not afraid of going a bit darker from time to time, either.
Regular Den Of Geek readers will know of our admiration for the movie choices of one Mr. Kevin Costner, and Tin Cup is no exception. A brilliant, intelligent and adult (not like that) romantic comedy, it reunites him with writer-director Ron Shelton (after the also-great Bull Durham), and sees Costner as a washed-up golf professional by the name of Roy ‘Tin Cup’ McAvoy.
One day, Rene Russo’s Dr. Griswold walks into his life, wanted golf lessons. She happens to be dating McAvoy’s old rival, David Simms, played in slimey fashion by Don Johnson. A love triangle is set up, but one that has the small matter of the U.S. Open golf tournament at the heart of it.
As with Bull Durham though, this is a film less about sport and more about relationships. We’d go as far as to argue it’s something of a modern classic of the genre. Mulligan, anyone?
The Truth About Cats And Dogs
What do you do if you’ve directed one of the most notorious box office disappointments of the 1990s? Michael Lehmann, coming off Hudson Hawk (a film we’ve explored our warming to here), went smaller. In fact, he picked out a quirky romcom by the name of The Truth About Cats And Dogs.
Lots of things work in its favor, but it’s the off-beat casting in particular. Janeane Garafalo is an entirely believable and human lead, hosting a radio phone in for people with animal problems. Enter Ben Chaplin – once upon a time mooted as the next big thing in Hollywood, remember – who has a problem dog. Then there’s Uma Thurman in the midst of it all. Shennanigans ensue, and whilst the romcom template is fairly religiously followed, Lehmann’s film crucially distinguishes itself by having characters you actually give two hoots about.
The Wedding Singer
It’s hard work watching Adam Sandler films. Blended attempted to recapture the chemistry that he and Drew Barrymore had managed before, but – whilst not his worst effort in recent times – it just serves as a demonstration as to how far the quality of Sandler movies had fallen. Answer: a lot.
The Wedding Singer, meanwhile, may have dated a little, but it’s a heady reminder of a time when Sandler played characters you could actually like. Played out to a soundtrack of ’80s pop hits, Sandler stars as Robbie Hart here, who has his heart broken, and then meets Drew Barrymore’s Jules. He agrees to help her plan her wedding and… well, y’know.
So why does The Wedding Singer work when so many other Sandler rom-coms don’t? A few reasons. It’s funny. There’s a couple at the heart worth spending time with. There are at least three scene stealing cameos (Billy Idol, Jon Lovitz and particularly Steve Buscemi). And it’s funny. That’s worth mentioning twice.
When Harry Met Sally
Even to this day, films continue to try and capture just what made When Harry Met Sally work. Take a look at the recent Daniel Radcliffe-Zoe Kazan feature, What If, which takes a not dissimilar approach. To be fair, there’s more than one way to tell the story of two friends who are faced with whether they should take things further, but there’s little doubt that When Harry Met Sally offers the definitive take. Meg Ryan and Billy Crystal share so many terrific moments here, served beautifully by Nora Ephron’s finest screenplay. And while it’s the orgasm scene that tends to get the most YouTube views, When Harry Met Sally barely puts a foot wrong for its duration. A genuine classic. And a very rewatchable one.
While You Were Sleeping
Sandra Bullock‘s skill as a performer was demonstrated early and right here for our money (well, not withstanding the infamous nookie scene in Demolition Man). For her character here should be horrible. She does something unpleasant, and yet still manages to keep you onside. And that ain’t easy.
She basically steps into the life of a man with amnesia, convincing his family that the pair are engaged. All the while, she foolishly ignores the attention of the charming Bill Pullman. A frothy comedy that could have gone a lot darker, it’s a bit twee, but worth it as a demonstration of Bullock’s screen presence.
“Nah.” Rarely has Harrison Ford delivered a line – at least outside of Indy and Star Wars – as exquisitely as his single word towards Melanie Griffiths’s Tess in Mike Nichols’s very ;80s rom-com, Working Girl. Whilst heavily billed on the poster alongside Sigourney Weaver, this isn’t Ford’s movie though. Instead, it’s the story of Tess, trying to make her way in New York, whilst her boss – played by Weaver in delicious form – is recuperating from a skiing injury.
It’s Melanie Griffiths’ best screen performance this too, and it does prove as well that Ford is an able comedy actor. Who doesn’t do enough comedy.
And finally… Love Actually
Presumably, you’d shout at us a lot if we stuck Love Actually in here. It’s actually excluded because the romantic comedy bits are arguably the weakest segments of the film. However, the drama between Alan Rickman and Emma Thompson, we’d argue, is five star gold. Shout away…
And when you’re done, please check out our previous list of 14 Romantic Comedies That Won’t Make You Cringewith (almost) no overlap!