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  Top 20 Romantic Comedies of All Time

 
 
 
 
Top 20 Romantic Comedies
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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.


Romantic Comedies give all of us a chance to laugh at the silly things we do in the name of love!

Couples Company has assembled a list of
our top picks of Romantic Comedies that actually work.  These are funny movies with strong storylines, 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 plotline.  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.

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Couples Company's Top 20 Romantic Films

Comedy
English
BUY

1

There's Something About Mary

1998: R
Starring: Cameron Diaz, Matt Dillon, Ben Stiller, Lee Evans, Chris Elliott
Director: Peter Farrelly, Bobby Farrelly
118 minutes

 
 

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?!?

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2
The Princess Bride

1987: PG
Starring: Cary Elwes, Robin Wright Penn, Mandy Patinkin, Chris Sarandon, Christopher Guest
Director: Rob Reiner
98 minutes
 

Often ranked as the top Romantic Comedies in polls by 20 & 30 something’s, for some reason the 50+ crowd doesn't get it, preferring instead Eating Raul (which 30 something'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. 


TOP


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Comedy
Fantasy
English
BUY
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Drama
Comedy
English
BUY
3
Sleepless in Seattle

1993: PG
Starring:
Tom Hanks, Meg Ryan, Bill Pullman, Ross Malinger, Rosie O'Donnell
Director: Nora Ephron
105 Minutes
 

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. TOP


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Drama
Comedy
English
BUY
4
Pretty Woman

1990: R
Starring:
Richard Gere, Julia Roberts, Ralph Bellamy, Jason Alexander, Laura San Giacomo
Director:
Garry Marshall
117 minutes
 

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. TOP


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Comedy
English
BUY
5a
The Philadelphia Story
 

1940: G
Starring: Cary Grant, Katharine Hepburn, James Stewart
Director: George Cukor
176 Minutes

 

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. TOP


 
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Musical
Comedy
English
BUY
5b High Society

1956: PG
Starring:
Bing Crosby, Grace Kelly, Frank Sinatra, Celeste Holm, John Lund
Director: Charles Walters
107 minutes
 

With Grace Kelly and Bing Crosby, how can you miss?  This classic, based upon the original 1940’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. TOP


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Comedy
Drama
English
6: Sex and the City

2008: R
Starring:
Sarah Jessica Parker, Kim Cattrall, Kristin Davis, Cynthia Nixon
Director: Michael Patrick King

Approximately 136 minutes
 

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:)

 

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Drama
Comedy
English
BUY
7

Annie Hall

1977: R
Starring: Woody Allen, Diane Keaton, Tony Roberts, Carol Kane, Paul Simon
Director: Woody Allen
93 minutes

 

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. TOP


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Comedy
English
BUY
8
The Seven Year Itch

1955: PG
Starring: Marilyn Monroe, Tom Ewell, Evelyn Keyes, Sonny Tufts, Carolyn Jones, Robert Strauss
Director: Billy Wilder
105 minutes

 

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 why Marilyn Monroe became the sex symbol of a dozen generations. TOP


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Comedy
English
BUY
9
My Man Godfrey

1936: G
Starring: William Powell, Carole Lombard, Alice Brady, Gail Patrick, and Eugene Pallette
Director: Gregory La Cava
93 Minutes

 

 If you love classic screwball comedies mixed with a little romance and a lot of dreaming, don’t miss this original version of My 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.   TOP


 
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Comedy
Fantasy
English
BUY
10

Shrek

2001: PG
Starring: 
Mike Myers, Eddie Murphy, Cameron Diaz
Director: Andrew Adamson, Vicky Jenson
93 Minutes
 

This is our only animated film and we are extremely delighted to include Shrek in our list of Top Romantic Comedies for two reasons.  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. TOP

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