The Greatest Romantic Comedies Of All Time

February is here which can mean only one thing…

…Groundhog leftovers.

…no, it means Valentine’s day.

Now, I’m single, and I understand the tendency of many of my fellow single people to loathe this holiday with a fiery passion.  I understand the frustration.  However, it is still a wonderful holiday that celebrates one of the best aspects that life has to offer.  Which means I should do a series of the best movies that deal with Romance…however I’ll be the first to admit that while some of these films I can watch over and over and over again, I’m not sure I can get a full blog out of them–some are a little short on philosophical depth.  So what I’m going to do is give you three lists.  The top 14 romantic comedies, the top 14 Romantic dramas, my favorite cinematic couples.  So let’s start with the Romantic Comedies.

I understand it’s very hard to rank comedies as there are lot of intangibles in the issues of taste when it comes to what is and isn’t funny…but here is my list, feel free to disagree in the comment box.

(LoveActually should probably be on this list, but as I put it on the Christmas list already, forgive that it is not being included).


Failure to Launch

“You were bitten by a chuckwalla. That shouldn’t have happened. It’s a reptile of peace. I have a theory. This isn’t the first time that nature’s lashed out at you like this. I believe it’s because your life is fundamentally at odds with the natural world. […] Therefore, nature rejects you. “

A stupid little comedy about doing that thing we all hated doing…growing up and moving out.  I can’t fully praise its virtues other than I really enjoy it.


Blind Date

“Oh Walter your beautiful car! Oh look on the bright side, what else can happen? “

Most have probably forgotten about this Blake Edwards film where Kim Basinger leads Bruce Willis on a blind date straight from the 10th concentric circle of Hell!  His car is destroyed, he loses his job, chased and beat up by a deranged ex-boyfriend (played by the hilarious John Larroquette), burns every business connection he has, and gets thrown in jail…and worst of all this glutton for punishment falls in love with her.  All the insanity you expect in an Edwards film (remember the original Pink Panther) in a romantic comedy.


America’s Sweethearts

“I’m grateful for you.”

A romantic comedy that makes fun about how stupid romantic comedies are getting (the newest film in the top 10 was written in 1995) and how everyone in Hollywood seems to be getting more and more annoying and screwed up with every passing year.  Quite frankly Hollywood needs to make fun of itself more often.  All of the characters are deeply screwed up, but you love watching them try to figure out their lives and loves.


50 First Dates

“There’s nothing like a first kiss.”

I am not a fan of most of Adam Sandler’s work (usually it’s a little too crass for my tastes) but 50 First Dates avoids most of that.  While completely impractical, there is something unspeakably sweet about a man who loves someone so much he will work to make her fall in love with him every single day.


Heart and Souls

Harrison: “Who came up with this ridiculous concept anyway? Resolve your entire life in one bold stroke? What if I fail? And I will. I’ll fail. I’m telling you. I always fail. Then my whole life will be a complete failure. “

Thomas:”No offense, Harrison. But you died a failure because you never tried.”

It’s hard to imagine a movie where two-thirds of the cast dies in the first 10 minutes being a comedy, but it is.  (Oh, wait until we get to the drama, there is death aplenty there…9 of the top 14 somebody dies in 2 others there is serious injury).  Four souls are given the chance to use Robert Downey Jr. to help them solve whatever problems they had in life.  This leads to some serious issues with Downey Jr.’s love life, which his personality was already ruining, but eventually everything gets worked out.  I’ll grant it’s more comedy than romance, but it’s still a good film.


ANY Spencer Tracy & Katherine Hepburn Comedy, but especially Desk Set & Adam’s Rib

“Well you know what the French say, viva la difference”

Do I even have to justify the works of these two?  A constant locking of heads and wills between two very intelligent, very stubborn people who whether it’s on film or in real life are completely in love.  These are comedies that never get old.



Democracy can be a wickedly unfair thing Sabrina. Nobody poor was ever called democratic for marrying somebody rich.”

If you think I meant that horrible remake, shame on you! I mean Audrey Hepburn and Humphrey Bogart…there exists no other version.  None.  Bogart and Hepburn are perfect in this story of love and business.


It happened one night

Alexander Andrews: Oh, er, do you mind if I ask you a question, frankly? Do you love my daughter?

Peter Warne: Any guy that’d fall in love with your daughter ought to have his head examined.

Alexander Andrews: Now that’s an evasion!

Peter Warne: She picked herself a perfect running mate – King Westley – the pill of the century! What she needs is a guy that’d take a sock at her once a day, whether it’s coming to her or not. If you had half the brains you’re supposed to have, you’d done it yourself, long ago.

Alexander Andrews: Do you love her?

Peter Warne: A normal human being couldn’t live under the same roof with her without going nutty! She’s my idea of nothing!

Alexander Andrews: I asked you a simple question! Do you love her?

Peter Warne: YES! But don’t hold that against me, I’m a little screwy myself!


Clark Gable and Claudette Colbert in this story of a reporter helping a rich girl escape her oppressive lifestyle for a story is nothing short of perfect (and the best writer, best actor, best actress, and best director Oscars this movie got seems to back up my point).  Probably nothing is funnier than when the fabled walls of Jericho come down.  (On a side note that will probably get me much hate mail, I don’t know why Roman Holiday isn’t more often referred to as a cheap rip off of It happened one night…because that is all it is, and one with a much crappier ending).


While you were sleeping

Lucy: So what should I do?

Jerry: Pull the plug.

Lucy: You’re sick.

Jerry: I’m sick? You’re cheating on a vegetable.

Sandra Bullock has been in a slew of romantic comedies but probably none is better than this one where a lie leads her to true love…although not with the man she thought she loved.  (Although I think Two Weeks Notice deserves an honorable mention, if for no other reason than the faces Hugh Grant makes throughout the film).  Personally I will always take Bullock in a romantic comedy over a drama (even though she is very good actress) but this is also one of those movies I look at and never fully understand why Bill Pullman doesn’t have a more successful career as he makes a perfect leading man in this bizarre comedy of errors.


My Man Godfrey

You mustn’t come between Irene and Godfrey. He’s the first thing she’s shown any affection for since her Pomeranian died last summer.”

The story of a ditzy socialite, Irene Bullock (Carole Lombard) who, upon finding what appears to be a homeless and destitute man who isn’t afraid to tell off her shallow rich friends, gives him a job as her household butler.  There this man, Godfrey (played by William Powell), finds that his ditzy boss is actually the best person in her family of thieves and idiots.  All of them look down on Godfrey for one reason or another at first because they assume from her story that he is poor as poor can be…to hell if he’s smarter and more honorable.  And of course there’s that other thing about the fact that he’s about ten times richer than they are, and had only been found looking like a bum after a year-long bender from getting his heart broken.  Of course Godfrey falls for Irene, against his good judgment, while rediscovering how to live life and not be simply self-pitying.

The comedies of William Shakespeare especially Branagh’s Much Ado About Nothing and As You Like It and Nunn’s Twelfth Night.

“One woman

is fair, yet I am well; another is wise, yet I am

well; another virtuous, yet I am well; but till all

graces be in one woman, one woman shall not come in

my grace. Rich she shall be, that’s certain; wise,

or I’ll none; virtuous, or I’ll never cheapen her;

fair, or I’ll never look on her; mild, or come not

near me; noble, or not I for an angel; of good

discourse, an excellent musician, and her hair shall

be of what colour it please God.”

In the history of writing there is a simple fact that no one has ever been able to exceed Shakespeare (there are some flaws in transferring it to film which is why this is only #4) but nothing has yet to outdo the Bard.

On film probably the best versions are the stories of Beatrice and Benedict and their constant snipping, the insanity of Rosalind and Orlando, and the madcap cross-dressing wackiness of the Viola/Cesario-Ovlia-Orsion triangle.  However I might add that I might have to movie Shakespeare to #1 for movies if Joss Whedon’s Much Ado About Nothing is as great as I hope it will be. (Also there was apparently a stage version with David Tenant as Benedict and Catherine Tate as Beatrice…dear god what I would have given to see that).


The 3 movies starring Cary Grant and Katherine Hepburn, Bringing up Baby, Holiday, The Philadelphia Story.

Now it isn’t that I don’t like you, Susan, because, after all, in moments of quiet, I’m strangely drawn toward you, but – well, there haven’t been any quiet moments.”

Tracy and Hepburn, great.  Grant and Hepburn, well it’s sad that the English language lacks a super-superlative.  But what would you expect when you team up the greatest actor of all time and the greatest actress of all time?  From the madcap insanity of Howard Hawk’s Bringing up Baby (and the only time I think I have ever seen Hepburn play a ditz) to the two more witty Philip Barry plays Holiday and The Philadelphia Story these two are always perfect together and can be watched over and over and over again without their genius ever losing anything.

Pretty Woman

“What happened after he climbs up and rescues her?”

She rescues him right back.”

The perfect modern interpretation of the classic fairy tale that acknowledges that love and rescuing in the field of romance is always a two way street (because he is in far more need of rescuing than she is).  You are not fully human if you don’t love this movie.

Honorable Mention: While not as good as Pretty Woman, Runaway Bride is delightful in how it plays off of all the little moments in Pretty Woman.

And of course…





I assume you want to know what the greatest romantic comedy of all time is…





Well since you asked for it…





All I can say is…






As you wish.




The Princess Bride

“Death cannot stop true love…all it can do is delay it awhile.”


It would say it is safe to say that 50% of the people reading this blog know every single line in this movie.

It never gets old.  It never ceases to warm my heart.  It could not be any better in any way shape or form.  It is perfect.

If anyone in Hollywood ever gets the idea that they can remake this movie, then the only punishment fitting for such arrogance and stupidity is death.  This movie is perfect for all ages, all times and circumstances.  There is nothing that can be improved. It is the greatest romantic comedy of all time and if you haven’t seen it then your life is unspeakably sadder for not having this in it.

Other Honorable Mentions in particular order:

Indiscreet, For Love or Money , Mr. Destiny, She’s All that, He said/She Said, I.Q., Just Like Heaven, Serendipity, Lady and the Tramp (not so much the whole movie, but the spaghetti scene), Heaven Can Wait


Filed under Art, Love, Movies

7 responses to “The Greatest Romantic Comedies Of All Time

  1. I’ve only seen one of those, and that’s because my then-husband happened to be watching it. I guess I’m not particularly into romantic comedies. But it’s interesting to see a list that really points out how not into them I am.

  2. chandlerswainreviews

    If I might be so bold to add “Love in the Afternoon” with Audrey Hepburn and Gary Cooper just about the sweetest May-December romance out there.

  3. Pingback: Happy Valentine’s Day (Movies and Mitt) | The Conservative New Ager

  4. Bella

    the fact that you say the princess bride is the best romcom of all time makes this whole list golden!! awesome movie and definitely the best romantic comedy out there!!

  5. Pingback: In preparation for Valentine’s Day… | The Conservative New Ager

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