Movies: Romantic Comedies
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The Sport of Courtship
The Top 25 Romantic Comedies
of All Time
By Laura Dawn Lewis


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.
 

 
Releasing Christmas Day, 2009 from Universal

Print PG 1    Print PG 2

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.
 
Featured Rankings

1-13

14-25

Number 1

Comedy
English


BUY

 
1998: R


Starring:
Cameron Diaz, Matt Dillon, Ben Stiller, Lee Evans, Chris Elliott
Director:

Peter Farrelly, Bobby Farrelly

118 minutes

There's Something About Mary


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?!?

 

Number 2

Comedy
Fantasy
English

BUY
 
1987: PG

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

 
5 stars.gif (1395 bytes)
The Princess Bride


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.   

Number 3

Drama
Comedy
English

BUY

 

1993: PG
Starring:
Tom Hanks, Meg Ryan, Bill Pullman, Ross Malinger, Rosie O'Donnell
Director:
Nora Ephron
105 Minutes
 
5 stars.gif (1395 bytes)

Sleepless in Seattle


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
 

Number 4

Drama
Comedy
English

BUY
 
1990: R
Starring:

Richard Gere, Julia Roberts, Ralph Bellamy, Jason Alexander, Laura San Giacomo
Director:

Garry Marshall
117 minutes
Pretty Woman

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.
 

Tie for  5

Number 5A

Comedy
English

BUY

 

1940: G
Starring: 
Cary Grant, Katharine Hepburn, James Stewart

Director: 
George Cukor
176 Minutes
The Philadelphia Story


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.
 

Number 5B

Musical
Comedy
English

BUY
 
1956: PG
Starring:

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

High Society


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

Number 6

Comedy
Drama
English
 

BUY
 

2008: R
Starring:

Sarah Jessica Parker, Kim Cattrall, Kristin Davis, Cynthia Nixon

Director:
Michael Patrick King

Approximately 136 minutes

 

 
Sex and the City

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:
 

Number 7

Drama
Comedy
English
 

BUY

 
1977: R
Starring:

Woody Allen, Diane Keaton, Tony Roberts, Carol Kane, Paul Simon

Director:
Woody Allen
93 minutes
Annie Hall

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

Number 8

Comedy
English
BUY
 
1955: PG
Starring:
Marilyn Monroe, Tom Ewell, Evelyn Keyes, Sonny Tufts, Carolyn Jones, Robert Strauss
Director:
Billy Wilder
105 minutes
 
The Seven
Year Itch
 
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

Number 9

Comedy
English
BUY
 

1936: G
Starring:

William Powell, Carole Lombard, Alice Brady, Gail Patrick, and Eugene Pallette

Director:

Gregory La Cava
93 Minutes

My Man Godfrey

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
 

Number 10

Comedy
Fantasy
English
BUY

2001:
PG
Starring: 

Mike Myers, Eddie Murphy, Cameron Diaz
Director: 

Andrew Adamson, Vicky Jenson

93 Minutes
 
Shrek

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.

TOP
 

Number 11

Comedy
Drama
Vintage English
BUY

 

1967, PG
Starring:
Richard Burton, Vernon Dobtcheff, Alfred Lynch, Elizabeth Taylor, Michael York
Director:
Franco Zeffirelli
122 minutes
The Taming
of the Shrew


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 in Ten Things I Hate About You.
 

Number 12

Comedy
Drama
English
BUY
 

1991: PG
Starring:
Richard E. Grant, Steve Martin, Victoria Tennant, Cal-Trans Freeway signs
Director:

Mick Jackson
98 Minutes

LA Story

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
 

Number 13

Comedy
English
BUY
 

1962: G
Starring:
Doris Day, Cary Grant, Gig Young
Director:
Delbert Mann

99 Minutes

That Touch
of Mink

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.

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