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Top 10 Romantic Comedies

Top 10 Best Romantic Comedies | Movies (With Clips) With a title like ‘Top 10 Best Romantic Comedy Movies’ there are bound to be certain… expectations. Let’s get this out of the way: there will be no films on this list that feature Matthew McConaughey or Hugh Grant. None. If that seems ridiculous/prejudiced/impossible to you… well, sorry.

So without further ado, here are the best romantic comedies. In date order.


Top 10 Best Romantic Comedies
(Boy Meets Girl)
C.C. Baxter works for an insurance company and has a major crush on Fran Kubelik, an elevator operator in his office building. Baxter’s a shy sort of fellow, lacking the confidence to ask out Miss Kubelik. His somewhat timid disposition is exploited by superiors at his workplace, who use his apartment to conduct extra-marital affairs. The arrangement results in his promotion, which bolsters his confidence, and he invites Miss Kubelik to see a play with him.

(Boy Loses Girl)
Baxter gets stood up, and returns to his apartment to find Miss Kubelik there, overdosed – she’d been having an affair with his boss.

(Boy Gets Girl Back)
Being the upstanding guy he is Baxter nurses Miss Kubelik for a couple of days, grows a spine, and quits his job. Miss Kubelik realises that Baxter loves and respects her, she quits, and then they play cards. Awwwwwww.

(Why It’s Cool)
Well, it was made in the sixties by Billy Wilder. And then there’s dialogue like this:
J.D. Sheldrake: “Ya know, you see a girl a couple of times a week, just for laughs, and right away they think you’re gonna divorce your wife. Now I ask you, is that fair?”
C.C. Baxter: “No, sir, it’s very unfair… Especially to your wife.”



Top 10 Best Romantic Comedy Movies
(Boy Meets Girl)
‘Chapter One. He was as tough and romantic as the city he loved. Beneath his black-rimmed glasses was the coiled sexual power of a jungle cat…’ Isaac (Woody Allen) is a 42 year old writer, twice-divorced, and dating a 17 year old girl named Tracy (Mariel Hemingway). His married best friend is having an affair with Mary (Diane Keaton). At first he can’t stand Mary, then he spends some more time with her and kind of starts to like her. Then his friend ends it with Mary and encourages him to ask her out. He does, dumping Tracy.

(Boy Loses Girl)
Mary gets back with Isaac’s friend. Not cool. Isaac gets seriously angry and tries to break them up.

(Boy Gets Girl Back)
This is where things get interesting. Because the girl he wins back? Not Mary. No, it’s Tracy. And it always was. And even though most of the romancing in the movie is with Mary it all makes perfect sense. It just feels right.

(Why It’s Cool)
Because it does the bait and switch on his dream woman. And it’s shot beautifully in black and white, and Rhapsody In Blue is in it, and it remains perhaps the greatest cinematic love letter to New York.


Comedy Romantic Movie
(Girl Meets Boy)
In this John Hughes classic it’s Samantha’s (Molly Ringwald) 16th birthday but – tragically – it’s being totally overshadowed by preparations for her sister’s wedding. While sneakily filling out a ‘how far have you got with a boy’ questionnaire in class, Samantha drops the sheet and it’s picked up by the class hunk (Michael Schoeffling). She’s written his name on it as her ideal man – so what happens now?

(Girl Loses Boy? / Girl Gets Boy Back?)
Not really. When you’re 16 the biggest obstacle is just getting the guts to say hello. Here it takes 83 minutes.

(Why It’s Cool)
Because it nails the adolescent panic over identity and how dramatic relationships feel at that age even when all you’ve done is exchange a glance. It’s cool because Molly Ringwald is cool. Because these are high school characters who are actually likeable. Because the house party is so destructive it puts a hole through two floors.


Romantic Comedies Top
(Boy Meets Girl)
Harry is dating a friend of Sally’s. They’re both leaving Chicago and heading to New York, which means – road trip! Aaaaaand they don’t get along. He persistently annoys her and conversation ends up heading in the direction of the nature of friendship: Harry doesn’t believe a man and woman can have a platonic relationship, he believes sex will rear its ugly head at some point, Sally disagrees.

(Boy Loses Girl)
Harry and Sally meet again years later and become really good friends, great friends, they have exactly the kind of platonic relationship Sally was talking about! Until they sleep together. And Harry freaks out and runs away…Moral of the story? Men are always right.

(Boy Gets Girl Back)
Harry realises he’s made a terrible mistake, and tells Sally he loves her. He gets her back.

(Why It’s Cool)
What makes all this enjoyable to watch is how amazingly well written the dialogue is, Billy Crystal and Meg Ryan are incredibly adept at sparring with each other verbally and despite the fact that virtually no action is taking place during the opening car scenes, it’s seriously compelling. It’s also cool because they’re not actively trying to pursue each other, or being kept apart by outside interference, they’re deliberately avoiding being together. And it’s funny, can’t forget the funny.


Comedy Romantic Movie
(Boy Meets Girl)
Bryan meets Annie in Rome, but because of how the Father of the Bride is set up, we find this out the way that George Banks finds this out – second hand, over dinner. And he’s more than a little resistant to the idea of his daughter being engaged…

(Boy Loses Girl)
But eventually he resigns himself to the idea and proceeds to organise the wedding of his daughter and Bryan. Until his daughter calls the wedding off. Why? Because Bryan bought her a gift, and that gift was a blender. Bryan bought his future-wife a kitchen appliance and she interprets this as confirmation of his notion of gender roles. End of relationship.

(Boy Gets Girl Back)
George ends up being the one to reconcile the couple, despite his initial opposition to the relationship.

(Why It’s Cool)
It’s an outside perspective on the Romantic Comedy. Steve Martin’s outside perspective. The regular romantic comedy plays out while Steve Martin loses his mind – what more could you ask for?

Best Romantic Comedies – Most Recent 5 >

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  • puppy said

    😀 my 3 faves:

    the wedding singer
    dirty dancing

    they rule! oh, yeah.

    Thumb up 0 Thumb down 0

  • Gem Harper said

    Sleepless in Seattle, Love Actually, Four Weddings and Funeral, Groundhog Day belong there.

    500 Days, Meet the Parents and Sideways? No way, sorry.

    Thumb up 0 Thumb down 0

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