Top 25 Romantic Comedies

Comedies are always hard to rate because what one thinks of as comedy is really a personal choice.  Romantic Comedies seem even harder to pull off and we had to dig deep to find really good movies.  Most Romantic Comedies are average and fade into oblivion once released.  These have stood the test of time.

Boy did we duke it out at Couples Company about this one.  Half the staff said, "Something About Mary isn't a romantic comedy!" The other half insisted it is. Once we dissected the script we confirmed this movie is in fact a classic romantic comedy storyline and our top pick. So what if it wasn't marketed as such. This is the one and only movie we know of that can make you cry because you are laughing so hard!  It’s the best cure for a tough day and if it doesn’t make you laugh, check your pulse.  Are you sure you are alive?

Set in 1985 and 1998, (Ted) Matt Damon is delightfully slimy as the voyeuristic private detective sent by the hopelessly bumbling (Ted) Ben Stiller to track down his high school sweetheart played by (Mary) Cameron Diaz. Lin Shaye (Magda) and Jenson W. Earl Brown (Warren) turn in great supporting performances.  This movie is full of surprises and leaves you guessing to the very end, what will happen next?!?


Often ranked as the top Romantic Comedies in polls by GenXers, for some reason the Boomer crowd doesn't get it, preferring instead Eating Raul (which Xer's think is rather strange!). 

The Princess Bride is so ridiculously satirical, it’s witty and intelligent.  The movie begins with Grandpa (Peter Falk) entertaining his sick grandson (Fred Savage) by reading him a story, the Story of The Princess Bride.  Robin Wright-Penn plays Buttercup, a landowner’s daughter who catches the eye of Prince Humperdink (Chris Sarandon).  Wesley (Cary Elwes) starts out the movie as her stable boy, and once he leaves, she realizes he’s her one true love.  He returns to find her betrothed to Prince Humperdink.  Following the classic boy gets girl, boy loses girl scenario. Wesley must brave giants, con artists, duels, fire swamps, sea monsters and a host of other hilarious obstacles to win back his love.  Mandy Patinkin, Christopher Guest and Andre the Giant also turn in memorable performances.

Rated as one of the top picks by 40 something’s, Sleepless in Seattle combines romance, comedy and the undeniable attraction of soul mates and long distance love.  Annie (Meg Ryan) is a journalist who after hearing a late night talk show where Sam’s (Tom Hanks) son laments that his father needs a wife, decides this man is for her. 

Two problems, she’s engaged and he lives on the other side of the country.  For anyone who has fallen in love long distance or wondered what it would be like,Sleepless in Seattle will have you cheering the potential and praying for a happy ending.

PRETTY WOMAN - 4.5 Stars

If you’ve ever believed in Fairy Tales, Pretty Woman is your kind of movie.  Vivian (Julia Roberts) is a Hollywood hooker, normally the last stop on society's track who happens to run into Edward Lewis (Richard Gere), an industrial tycoon/corporate raider. 

At first, he tries to keep it all business.  Stating all he needs is a date for the week and no romantic entanglements.  But within days he falls for the vivacious and slightly unconventional Vivian.  Both characters go through dramatic personal changes and the fairy tale ending is one of the reasons,Pretty makes the top 5 list of the Best Romantic Comedies.


This is a movie for anyone who has fallen in love and lost him or her and would really like a second chance.  Katherine Hepburn plays Tracy, a member of Philadelphia society about to marry another man.  On the eve of her wedding, ex-husband Dexter (Cary Grant) shows up and completely messes with her resolve. 

Two photographers are present to record the next day’s events, only one, played by James Stewart falls in love with the beautiful Tracy.  Twelve hours before her wedding, Tracy now has 3 men vying for her attention.  She does marry one in the end, but not whom you think.  Considered one of the top screwball comedies, Philadelphia story captures the pre WWII innocence and imparts several ominous lines, one specifically relating to holocaust, six years before this fact comes to light.

  HIGH SOCIETY - 4.5 Stars

With Grace Kelly and Bing Crosby, how can you miss?  This classic, based upon the original1940’s Philadelphia Story(above) and covers the intriguing involved when winning the heart of someone who’s taken with a 1950's update.

Socialite Tracy (Grace Kelly) is preparing to marry her very predictable and boring fiancé, George (John Lund) when her ex from the past (Bing Crosby) shows up intent on winning her back.   Antic’s, saucy dialogue, beautiful costuming and Louis Armstrong make High Society an engaging and silly romantic comedy that regardless of age, all will enjoy.

High Society was Princess Grace’s last film before her marriage

SEX AND THE CITY - 4.5 Stars

I haven't had this much fun at a movie in years and guys will brand this a 'chick flick' but it really has enough sexual innuendo and eye-candy to keep even the most reluctant man entertained.  This comedy follows the classic boy meets girl, boy loses girl, boy gets girl back in several story lines. 

The characters from the hit television show are fabulous and the entire film gives you the feeling that life after forty is fabulous.  Women will really love the close friendships and the way each of the characters supports the other.  Men will adore the comedy and the inside jokes women have about men.  In the theaters at this writing but without a doubt, a fabulous rental once available.  Plan on sushi for dinner.

  ANNIE HALL - 4 Stars

Winner of the Academy Award®for Best Picture 1977, Annie Hall is one of Woody Allen’s masterpieces covering the romantic ups and downs of a Jewish writer (Woody Allen) and a Protestant singer (Diane Keaton), circa 1970’s.  

Playing upon the opposites attract and then make good comedy trying to figure out how to make the relationship work,Annie Hall delivers in both entertainment and laughs.  And winning the Best Picture award was no small feat...Star Wars was its main competition.


What does a married man do when his wife leaves for the summer and Marilyn Monroe moves in above him?  This is the movie with the white dress flying up that left an indelible memory on the minds of men for decades to come. 

From “Undies in the ice box” to a number of coquettish lines of innuendo, The Seven-Year Itch is the epitome of whyMarilyn Monroe became the sex symbol of a dozen generations. 


If you love classic screwball comedies mixed with a little romance and a lot of dreaming, don’t miss this original version ofMy Man Godfrey.  It’s the story of an heiress (Carol Lombard) who finds a bum at a dump (William Powell) and transforms him into a butler and a respectable person. 

Unbeknownst to her, he’s actually a millionaire who is soured on love and decided to drop out of society.  She has designs on marrying him, much to her parent’s dismay.  He has ulterior motives, wanting to teach the filthy rich a few much-needed lessons in humility.  Released in the waning days of the great depression, this film takes you back to a simpler time when issues, like the film were generally black and white.

SHREK - 4 Stars

This is our only animated film and we are extremely delighted to include Shrek in our list of Top Romantic Comedies for two reasons.  First, we really like the main message of the movie: “It’s not what is on the outside that counts but the heart that makes a person beautiful”. 

We also are really happy to see DreamWorks SKG hitting its stride; call it payback for all of the naysayers in the late nineties.  During this time Hollywood elite were brutal toward this new studio.  This hilarious romantic comedy mixes together all of the genius that define DreamWorks dream team and founders Spielberg, Katzenberg and Geffen. 

You’ll love it and your older kids will love it!  The humor is witty and the story is inspiring.


William Shakespeare had a gift.  Not only could he write some of the best tragedies of all time, he was one heck of a comedic writer.  Not necessarily the original film version, this is the best.

First, the definition of a shrew: It’s either a small rodent with pointed nose or a scold, defined as one who berates and chastises others. The shrew (Elizabeth Taylor) is the eldest daughter who is sour on love and basically major high maintenance.  Her younger sister wishes to marry, but can’t until her older sister does.  She and her fiancé cook up a plan and convince someone (Richard Burton) to marry her sister so she may marry.  Staying true to Shakespeare’s original script and lavish costuming from the period, this film introduces you to the satirical, yet amusing aspirations of love. A more modern version can be seen inTen Things I Hate About You

LA STORY - 4 Stars

We choose LA Story because it is so unusual.  Steve Martin wrote this lighthearted look at love, middle age and freeways that endures as one of the best comedies, romantic or not written in the past 50 years. 

The good news is you don't have to be from LA to get it!  It's the story of a local weatherman searching for love.  He tries the younger 20 something woman (Sara Jessica Parker) only to discover he really wants a woman of more substance.  Unlike the typical LA person, rather than going to a psychotherapist, his romantic advice comes from a freeway sign, one that speaks only to him. 

Ultimately, he realizes the true love of his life is a woman closer to his age (Victoria Tennant), a journalist with a passion for tuba playing.  This is one of Martin's best works both on screen and written.   He has an uncanny ability to meld human emotion, trial, tribulation and comedy as in Roxanne(1987).  He proves this again in 1994 with A Simple Twist of Fate.


We couldn’t do a top romantic comedy selection without having Doris Day in at least one of the choices.  That Touch of Mink is not Academy Award material, but does deliver the hijinks and hilarity so often missing from most romantic comedies.  Produced before the pill, the Beatles, animal rights activists and the sexual revolution,

 That Touch of Mink harkens back to the simpler days when everything appeared perfect.  Of course now, we know it wasn’t.  Either way, it’s a silly and romantic way to spend and evening.


Finally a romantic comedy about what it is really like to be a thirty-something single female in a modern world.  So Bridget is a little more obsessed (NOT!) than most women with her weight, lack of sex during the peak years of her sexuality, the poor choices in men available and her gorgeous boss (Hugh Grant).  The boss is Mr. Mega Wrong in may ways. 

Unfortunately, Mr. Right (Colin Firth) lets his mother dress him and has no idea how to be assertive in love.  Bridget Jones' Diary is the romantic comedy in reverse: girl gets boy, girl loses boy, girl realizes its true love running through the snow barefoot in her underwear.  
Some guys get this movie (if he gets Ally McBeal he'll get Bridget Jones) and some can't believe that when women are alone we can really eat a half gallon of ice cream and be that neurotic about the absence of love...or that stupid in our choices!


A wartime romantic comedy of errors this movie reminds us of how much this country’s moral expectations have changed in just 60 years.

What happens when a young woman just wants to send the troops off happy and gets too drunk only to find herself married…and pregnant the next morning? 

Only she doesn’t remember getting married, who she married or most of the evening!  In 1944, single motherhood is still taboo and how Trudy (Betty Hutton) solves this dilemma and ultimately gives birth to a Miracle in Morgan’s Creek will have you chuckling all night long


Adam Sandler has become the Pied Piper of Gen-Y comedy and bathroom humor, but this movie is a little more sophisticated and appeals to an older audience.  Part of the fun of this movie is looking at the fashions of the mid-1980’s.   Okay, the hair was a bit big but they weren’t as bad as the stuff from the 70’s that today’s teens think are hip.  Look for eighties fashions to retread about circa 2005.

Robbie (Adam Sandler) is a less than talented singer at weddings who falls for the betrothed Julia (Drew Barrymore).  Both are currently in bad relationships, but trying to keep them together.  Of course, love conquers all, with the help of Billy Idol of course.  Gen Xer’s will love the flashback to High School/college soundtrack and Boomers will empathize with the situation and lament their free wheeling yuppie days. Overall, you’ll laugh at the movie and the fact you once dressed like that!


Fast-talking, rapid-fire remarks, quick plot twists and the stealing back of an ex before she marries another, His Girl Friday is romantic comedy on speed!  And if you like your romance lazy, this film will drive you nuts. 

But, if you like the underdog winning and smart dialogue, this classic will leave you in stitches…but your English better be up to par!  Even if it had subtitles, we don’t think you could read them fast enough to keep up!

ENCHANTED - 3.5 Stars

This is an original screenplay that is a pure delight.  Giselle (Amy Adams) is a soon to be princess who is sent from fairytale land by her proposed evil mother-in-law queen (Susan Sarandon) into modern day New York City where she falls off a billboard she mistakes for a palace into a divorce attorney's (Patrick Dempsey) arms. 

His daughter is convinced Giselle is a really princess and Giselle, with her fairytale land sensibilities proceeds to charm Dempsey.  Meanwhile Prince Charming with a talking chipmunk  comes after her followed by a henchmen of the evil mother-in-law and the games really begin.  Silly, funny and very romantic, this is a wonderful film that will leave you feeling all the warm fuzzies you can handle and dreaming of 'Happily Ever After'!

CLUELESS - 3.5 Stars

One of the problems about being an adult is sometimes really good movies come out, but we pass on them because we think it’s a teen thing.  Clueless is one of those movies.  Cher (Alicia Silverstone) plays a modern day Emma, meddling in the love lives of all of her friends, and finding a project Tai (Brittany Murphy) to create into a new femme fatal.  Of course, like Jane Austin’s heroine, the harder she tries, the more she screws up.  What we liked best about this romantic comedy is it’s insight into some of the ridiculous things teens due to look cool and how, even the teens think it’s crazy. As Sixteen Candles epitomizes 1980's teens, Clueless gives the next generation a movie of their own.  The script is fresh, hilarious and an adaptation even Jane Austin would approve of.


The first of the delightful screwball comedies of the 1930s, It Happened One Night was also the first film to sweep up every major Academy Award. It is one of those movies where all the elements came together magically: Robert Riskin's charming script, Frank Capra's superb direction, and two sparkling performances by Claudette Colbert and Clark Gable.


Janeane Garofalo (Abby) is the every-woman’s hero and her satirist attitude is played to the hilt in this ménage de troi of mistaken identities and stand-in’s.  Abby, an on air personality falls for a voice of a call in caller, Brian (Ben Chaplin). 

Sparks ignite and he asks her out.  The problem is, she has described herself as tall, blond and slender, which she’s not.  Convincing her neighbor (Uma Thurman) to go out with him for her, a dating-talking love triangle begins and Brian begins to think this woman Abby has a split personality, or worse.  Ultimately, which woman will get the guy?


Action, adventure, bad guys, romance, hidden treasure, drug lords and the undeniable chemistry of Douglas and Turner make Romancing the Stone one heck of a wild, comedic ride through the jungles of Columbia.  This film broke Michael Douglas into super stardom and entrenched Kathleen Turner as not just a sexy actress but a darn good one with a flare for comedy.  This is the perfect movie if you're looking for some light hearted, heated action mixed with a little romance and don't want to think too much.  Danny De Vito also turns in a winning supporting performance as the bumbling bad guy and the trio of actors went on together to create two other films: The War of the Roses and the sequel to this film, The Jewel of the Nile.

YOU'VE GOT MAIL - 3.5 Stars
Meg Ryan and Tom Hanks join together again with the incredible chemistry that worked so well in Sleepless in Seattle.  This movie is good, but not quite the caliber of the first.  Still, it's worth watching and it is definitely the best thing that has ever come along for the online dating industry.  The story centers around a small boutique bookseller (Meg Ryan) and the mega superstore bookseller (Tom Hanks) who moves one of his Barnes and Noble style stores into her neighborhood and ultimately puts her out of business.   Unbeknownst to both, the online flirtation they have been engaging in is with each other.


What if you are about to turn sixteen years old and everyone in your family has forgotten about your birthday because they are consumed with your sister’s wedding to a total loser?  And what if while all of this is going on you’ve got the biggest crush on the BMOC, but you’re being chased by the school’s biggest dweeb, who happens to sell tickets to the underclassmen for a buck to see your underwear? 

During the 1980’s, Director John Hughes was the king of teen angst. Sixteen Candles is one of his best.  Others includeThe Breakfast Club, Pretty in Pink,and Ferris Bueller's Day Off.  For anyone who has ever had a crush, lived through humiliation in high school or just plain survived their teens, regardless of age, you’ll love and relate to this smartly written and wonderfully acted comedy about first crushes and first loves.

THE APARTMENT - 3.5 Stars 

While the film starts off as a naughty-for-its-time sex comedy about sad sack C.C. Baxter (Lemmon) who discovers he can curry the favor of his many bosses by letting them use his apartment for romantic indiscretions, it takes a more serious turn when we get to know Fran Kubelik (MacLaine), an elevator operator with precious little self-esteem.

While most of the women Baxter's superiors lure to the tiny den of seduction look like brassy bar girls who've been this route before and know what they're doing, Kubelik is at heart a sweet (if disappointed) girl who desperately wants to be loved and who has made the mistake of falling for the duplicitous J.D. Sheldrake (Fred MacMurray). 

MOONSTRUCK - 3.5 Stars

A modest romantic comedy that proved an unlikely Oscar powerhouse, has weathered the passage of time far better than most '80s films.

The virtuoso performances certainly figure in the picture's enduring appeal: Top-billed Cher and supporting player Olympia Dukakis both walked off with Oscars, while up-and-comer Nicolas Cage and character actor Danny Aiello also delivered hilarious turns.

HITCHED - 3.5 Stars

There seems to be a racial divide in romantic comedies, one that doesn't exist in traditional comedies.  Hopefully that will begin to change. Some of the best comedians out there are African or Latino Americans. However in the past decade,  there have been several good romantic comedies with leading characters from the Latino and African American communities including  'The Holiday' and 'Confessions of an Angry Black Woman' and Spanglish, which is sweet.  We've chosen Hitch as the best of the lot and rip roaring good time!

Best Romantic Comedy Movies

Couples Company has assembled a list of  our top picks of Romantic Comedies that actually work.  These are funny movies with strong story lines, minimal bathroom humor, great characters and witty dialogue that are sure to leave you rolling off the couch and into each other’s arms.  You will be surprised at some of them because they were not marketed as “Romantic Comedies”.  In actuality, they are.  A romantic comedy is about the relationship between a man and a woman and generally follows the boy gets girl; boy loses girl, boy gets girl back plot line.  It can also be created around the trials, tribulations, arguments, misunderstandings, frustrations and general blunders we all encounter in the game of love.  Here are Couples Company’s picks for the Top Romantic Comedies of All Time.

Bill commented on 23-Aug-2011 03:46 PM4 out of 5 stars
Thank you for this list. I look forward to sharing it with my significant other.
Anonymous commented on 28-Aug-2011 04:56 PM3 out of 5 stars
I recommend Late For Dinner from 1991. As I noted in my review for "Quest For Love", there are very few films in the SF/Romance genre. It is, after all, a tough combination to do right. Fortunately, "Late For Dinner" does it right. The plot has some similarities
to Mel Gibson's "Forever Young". Both are the stories of someone being the guinea pig for a cryonics experiment, only to be thawed out many years in the future when their mate has aged without them. In this case, two brothers are frozen after an accident sends
them on the run, accused of murder. One is Willy, a family man devoted to his wife and daughter. The other is Frank, mildly retarded and slowly dying of a degenerative incurable disease. Frank has become part of Willy's extended family, with everyone accepting
his oddities and looking out for him. The issues we care about are the love story between Willy and his wife and whether there will be a cure for Frank's disease by the time he's thawed out. What raises this above the Gibson film is that you believe from the
beginning that the romantic leads (Willy and his wife) are really in love. The relationship of the two brothers is caring without being idealized - they fight and argue, but you believe in how much they really care for one another. In "Forever Young", the
characters display none of the depth of feeling that you associate with real love. Gibson's character lives in the world of Hollywood script writers where all relationships are self-gratifying and transitory, while this film is firmly rooted in the world we've
hopefully all lived in at some point in our lives and would like to believe we could live in forever. The performances are excellent - touching without being maudlin. The three principles - Brian Wimmer, Peter Berg, and Marcia Gay Harden - are all totally
believable. Sure, this movie may be a bit on the predictable side, and the whole cryo-stasis thing might be a bit hard to swallow, but once you're able to get to the suspension of belief, what's left is a sweet, sentimental movie that's perfect for you and
your special someone to cuddle up to as you watch. Funny and sweet, this is the perfect movie for a quiet night alone with your honey. If you consider yourself at all a romantic (love conquers all...and the like), you'll love this movie.

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