25 Best Romantic Comedies of All Time
The genre is full of movies with the same tired story and the same tired tropes. So, it's worth asking: are there any good romantic comedies? If so, which are the best?
Worry not, for I have mined through 90 years worth of films to offer you the 25 best romantic comedies. Now, before we begin you'll notice there are several romance movies NOT on the list: Romeo & Juliet, An Affair to Remember, The Princess Bride, the Before trilogy. Those are all fairly great films. However, I limited strictly to just the films that were comedic love stories - not tragedies, not fantasies, not musicals. Coincidentally, all of the films on this list take place in the time they were filmed, with one exception.
So steel thy heart, prepare to be wooed and lets get on with the countdown.
Pretty Woman (1990)
The classic modern romantic comedy, perhaps the late Garry Marshall's best. Although, the further we get from the late eighties (when it was filmed) the more dated and flawed this film becomes. Still, one can't deny the chemistry between Richard Gere and Julia Roberts.
24. Enough Said (2013)
Nicole Holofcener's middle age romantic comedy starring Julia Louis-Dreyfuss and the late James Gandolfini, who passed away four months before this film's release. It falls under the "conflict arises from someone not being honest" trope. However, that structure is wrapped around a beautiful story about middle age love and endearing performances by its leads.
23. As Good As It Gets (1997)
Jack Nicholson stars as an obsessive-compulsive with no social filter. He doesn't mean to be an asshole, but he meets Helen Hunt's waitress who "makes him want to be a better man." Scruffy, yet incredibly sweet.
22. Forgetting Sarah Marshall (2008)
Jason Segel became a star with this comedy co-produced by the great Judd Apatow. Segel flies to Hawaii to get over his vacuous, cheating ex (Kristen Bell), only to find her there with her new rock star boyfriend (Russell Brand) and falls for the enigmatic Mila Kunis. Hilarious, original, and one of the few romantic comedies from a guy's point of view.
21. Clueless (1995)
Director Amy Heckerling smartly adapts Jane Austin's Emma for '90s Beverly Hills with Alicia Silverstone in the role of the well-meaning, socially-deft, yet otherwise superficial Cher, who decides to play match-maker. Brilliant for its time, quotable, and still holds up, despite the dated fashions.
Shakespeare in Love (1998)
The one period piece on this list. Maybe shouldn't have won Best Picture at the Academy Awards, but still holds up as a crowd-pleaser. Witty writing, enjoyable premise, fantastic cast.
19. Harold & Maude (1971)
The one cult classic on this list is quirky, yet tender. Rose Gordon is a delight as the elderly woman who teaches a boy (Bud Cort) obsessed with death to live and love.
18. The 40 Year-Old Virgin (2005)
The one that launched Judd Apatow as the decade's greatest comedic director is also, coincidentally, his most lean at just short of two hours. Steve Carell is a perfect mix of awkward, sweet, and hilarious. An original premise that turns romantic comedy gender conventions on its ear.
17. Say Anything... (1989)
The directorial debut of Cameron Crowe (Jerry Maguire) leans more towards drama than comedy during its third act, but John Cusack and Ione Skye are charming as two high school graduates that are opposites who attract before she goes to college. A lot more meat on this bone than your typical rom-com.
16. Love Actually (2003)
British hit maker Richard Curtis's directorial debut is a wonderful pastiche of different relationships and stages of romantic love. Now considered a Christmas classic, in part thanks to Bill Nighy's hilariously horrendous 'Love is All Around'. Brilliant cast all-around.
Notting Hill (1999)
Julia Roberts was, for a while, known for her romantic comedies and dramas. This was her best. Hugh Grant is at his most bumblingly charming here.
14. Amelie (2001)
A film about bringing happiness to oneself, as well as others, and filling that loneliness in your life. Amelie (a sort of French version of Jane Austen's Emma) is a beautiful, quirky film that casts a spell on its audience quite quickly.
13. Groundhog Day (1993)
Yes, the film is largely about Bill Murray's sardonic weatherman being forced to repeat the same day in a small town over and over again. But what you might not remember is it's love that breaks him free from his curse.
12. High Fidelity (2000)
It might not make my Top 5 Best Romantic Comedies of All Time, but it gets points for being incredibly relatable and having a refreshingly mature take on love and romance: it's not all about the fantasy. For those tired of the fantasy. Also features a hilarious early Jack Black performance.
11. Waitress (2007)
An indie movie about a pregnant woman (Keri Russell) who resents her unborn child and is in an abusive relationship doesn't exactly sound like the kind of thing that will warm your heart. But it does make it as fresh as those creative mood-inspired pies we see close-up shots of her making. The romance ignites when she meets the new gynecologist in town (Nathan Fillion). But the film is about loving those unexpected people in your life.
There's Something About Mary (1998)
The Farrelly Brothers best film by far, a film they have never been able to match or improve on. There's Something About Mary is both raucous comedy and sweetness. I think one of the reasons why the gross-out gags in There's Something About Mary rises above the usual infantile material the Farrelly Brothers were usually known for is because each moment - be it the franks and beans on prom night, the bodily fluid hair gel, or the fish hook in mouth - all have a 'Wouldn't it be embarrassing if...' quality to them that is all the more sympathetic because of Ben Stiller. Ben and Cameron Diaz, whose career exploded after this film, are the emotional center of the film. Diaz plays the titular dream girl who, while trying to live her life, is oblivious to the vultures circling around her. Stiller plays a man who never stopped thinking about Mary, but is devoid of sleaze and desperation of the other men who falls under Mary's spell. There's Something About Mary is one of the most hilarious comedies of all time and best romantic comedies ever made.
(500) Days of Summer (2009)
Arguably, the greatest romantic comedy of the last 20 years, (500) Days of Summer is as close to the Annie Hall of today as can be found. Zooey Deschanel plays the titular character Summer with whom Joseph Gordon-Levitt's Tom has fallen in love. We see the relationship from the unreliable perspective of Tom, including a clever morning-after dance scene and a brilliant 'reality vs. expectation' sequence. This is a film that isn't interested in following a formula towards a happy ending. This is a film about how romantic comedies can warp our perspective of romantic relationships. It is an underrated gem and should be celebrated by everyone who loves romantic comedies and looks for movies that say something about love and relationships.
Broadcast News (1987)
Most people born after 1985 probably aren't aware of this James L. Brooks romantic comedy, which is a shame. Not only is it one of three great romantic comedies of its decade, but it is one of the best love stories, as it features a romantic triangle between go-getter news producer Jane (Holly Hunter at her best) and two TV reporters: her Everyman buddy, Aaron (Albert Brooks), and handsome newcomer Tom (William Hurt). Both are vying for Jane's heart, but take very different approaches to doing so. Aaron, being Jane's friend, is the caring-to-a-fault shoulder to cry on. Tom feels connected to Jane through their work, shared ambition, and good looks. Brooks, who is also the screenwriter, adds another layer here, which serves as a commentary on network news and its transformation from being genuine reporting and substance to superficial info-tainment. As such, one love interest represents substance and things that matter while the other represents news as theater. This makes Broadcast News somewhat prescient, as it's about something that only grew to monstrous levels since with the O.J. Simpson trial 6 years later and the eventual domination of 24-hour news coverage. Broadcast News is a great film that is currently underrated and too-often overlooked by audiences today.
It Happened One Night (1934)
The original romantic comedy as we know it: two leads of opposing personalities and backgrounds clash and soon fall in love. Starring Clarke Gable and Claudette Colbert and directed by Frank Capra, It Happened One Night influenced a thousand imitators. Every 'opposites attract' or 'on the road' romantic comedy you've seen owes a debt to this film. And it's still a delight. Not only that, but apparently reporters are a great source of romantic chemistry; you've got Groundhog Day, Broadcast News and It Happened One Night all on this list, all featuring reporters falling in love. There still might be room for one more on this list later on...
6. Sleepless in Seattle (1993)
The second of the partnerships between Meg Ryan and Tom Hanks is the best - and they don't even share the screen for most of the movie! He's a grieving widow and single father who is getting back into the dating pool; she's a fiancee on the other side of the country who's having second thoughts about her pending marriage once she hears his story on public radio. It's charming, sweet, funny, and irresistible. Movie lovers and rom-com aficionados will love the references to An Affair to Remember, a melodramatic weepie that ends up paling in comparison to this, director Nora Ephron's best film.
City Lights (1931)
Chaplin's most romantic film. With City Lights, Chaplin mixed his normal social commentary with a rom-com focused story. If you haven't caught up with it yet - and you should - Chaplin's Tramp character falls in love with a blind girl (Virginia Cherrill) who mistakes him for a rich man. The Tramp does everything he can to raise money for treatment to cure her blindness, including hilariously dodging his way through a boxing match. People talk about classic rom-coms, well, City Lights is a classic romantic comedy in every way.
Whoever said remakes suck has never seen His Girl Friday. Rosalind Russell plays Hildy, a fast-talking reporter who pays a visit to her newspaper editor ex-husband (Cary Grant) to tell him she's leaving the paper business behind to settle down with an insurance man (Ralph Bellamy) in this remake of The Front Page, itself an adaptation of a stage play. Director Howard Hawks and screenwriter Charles Lederer, a frequent collaborator with Hawks, changed one of the main characters into a female for this remake and what resulted was one of the best romantic comedies ever made. The film is known for its rapid-fire line delivery. Not three minutes into the film and the two romantic leads start spitting some of the fastest, cleverest dialogue imaginable until they're interrupted - or one of them caves. Grant and Russell are electric together, bouncing off each other in ways we rarely see today. The film is a delight for that alone. But as Grant's character schemes to get his gal back - save her from a life he deems to dull to be worthy of her - His Girl Friday becomes a fantastic screwball comedy. Not only that, but the film's subplot serves as a surprising critique on the hypocrisy of the news business that predates Broadcast News by forty years. His Girl Friday is a delightful romantic comedy and one of the greatest remakes ever attempted.
Bringing Up Baby (1938)
The ultimate screwball comedy - some have called it the first! If you haven't seen Bringing Up Baby - coincidentally, also directed by Howard Hawks - then you haven't seen Katherine Hepburn do comedy. You know that fast-talking wit Rosalind Russell fires off in His Girl Friday? Well, Hepburn did it two years earlier to dizzyingly daffy effect. Hepburn stars as well-to-do, yet scatterbrained Susan, who bumps into Cary Grant's wound-up paleontologist David. The plot is nearly impossible to explain, but it involves a leopard named Baby, a missing dino bone, a dog with an appetite for bones, and David's impending nuptials. One thing leads to another, Susan falls for David and practically makes a mess of everything she touches. Where it would've been quite irritating with a lesser actress, Hepburn is all charm. Grant is a put-upon nerd this time, which is surprisingly believable, given his charm and good looks and - when put against Gunga Din, His Girl Friday, or any other role of that time - really demonstrates his range as an actor. Bringing Up Baby was a big step forward from It Happened One Night for romantic comedies. It didn't necessarily try to convey any substantial insights about love or provide social criticism. What it did was take the 'opposites attract' concept a step further and say, "Sometimes love is nutty. Just enjoy the ride."
When Harry Met Sally... (1988)
The fake orgasm. The orders "on the side". The "pepper in my paprikash". The documentary interviews. The endless amounts of quotable dialogue. There are so many things that make Rob Reiner's iconic romantic comedy great. One could say its question about whether or not a man and a woman can retain a platonic relationship while single is one of those things. Or it's Nora Ephron's incredible script, which follows the titular characters from a post-college road trip through the years as they flow in and out of each others lives into their thirties. I say: 1) it's especially the cast with the sidekicks-turned married couple played by the now-deceased Carrie Fisher and Bruno Kirby, who offer both terrible advice to the leads, respectively, and a patient ear (if at times accompanied by an eye-roll) to their friends. And, of course, the leads, Billy Crystal and Meg Ryan, both at the height of their game, who play off each other so wonderfully, no matter if they're bickering or joking around. 2) What makes When Harry Met Sally... great is all the above. With all of this balled up in its 96 minute run time, as well as the 'guy runs after girl' trope and sweetness throughout, When Harry Met Sally... is one of the greatest romantic comedies of all time.
Annie Hall (1977)
It's hard to believe Annie Hall, arguably Woody Allen's greatest masterpiece, was originally conceived as a mystery with a subplot that grew into the movie we know! Sometimes the creative process takes you in a completely different direction and in this case it's towards greatness. So, why is Annie Hall a great film and the greatest romantic comedy of all time? Like #2 on this list, which followed just over a decade later and owes a lot to this film, there are a lot of things that make the film what it is. You have Diane Keaton's iconic fashion. Hilarious fourth wall breaking moments like the juxtaposition of Annie's and Alvy's (Woody Allen) families or when Alvy pulls media intellectual Marshall McLuhan into an argument in line from out of nowhere. Brilliant moments like the animated argument or the 'what is said' vs. 'what is meant' subtitles. And, of course, the jokes like, "That sex was the most fun I've ever had without laughing." There's all of this and more, but what elevates this film and showed Allen was ready to take his work to the next level is its examination of relationships. Whether it's through voice over or to another character, Allen, as Alvy, is frequently commenting on relationships, comparing it to a shark ("It has to constantly move forward or it dies") or quoting Groucho Marx ("I would never want to belong to any club that would have someone like me for a member"). This is not a film that is interested in formulas or tropes. It isn't interested in happy endings. It has a lot more to offer - and every great film should have more to offer than the minimum. As such, Annie Hall is one of the most influential films of its genre. Movies like When Harry Met Sally... and (500) Days of Summer wouldn't exist if not for Annie Hall. It may have been the first Hollywood movie to try to say something about love in a comedic way, to offer more than archetypes and genre tropes, but to really get at something and show a romantic comedy doesn't have to end with 'Happily Ever After'. Love or hate Woody Allen's style, Annie Hall is unquestionably a significant entry in the genre. I contend it is the greatest romantic comedy ever made.
Those are my picks for the 25 Best Romantic Comedies of All Time. Do you agree or disagree? Leave a comment below. If there's a film on this list you haven't seen, consider checking it or any of these movies out during your next date night, anniversary or Valentine's celebration. You won't regret it.