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.

THE APARTMENT (1960)

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.”
Genius.

MANHATTAN (1979)

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.

SIXTEEN CANDLES (1984)

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.

WHEN HARRY MET SALLY (1989)

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.

FATHER OF THE BRIDE (1991)

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?

GROUNDHOG DAY (1993)

Boy Meets Girl
Bill Murray is Phil, a weatherman begrudgingly covering the Groundhog Day festivities in Punxsutawney. Rita, his producer, thinks he’s a jerk. Because he is a jerk. He’s a sour-faced, gloomy, whiny, self-important jerk. It’s hilarious.

Boy Loses Girl
Phil, like most weathermen, is actually not able to predict the weather, and get’s trapped in Punxsutawney during a crazy-ass blizzard. But not any old crazy-ass blizzard, a cosmic time-loop-inducing crazy-ass blizzard. Phil relives the same day over and over and over and over and over and over and over and over and over. He starts to abuse the situation, because none of his jerky jerkishness has any consequence. He starts to abuse the situation, because none of his jerky jerkishness has any consequence. He tries to get Rita to fall for him, and fails. But Rita inspires him to be a better person.

Boy Gets Girl Back
Phil realises the error of his ways, he does everything he can to be the kind of person that deserves Rita’s love. He breaks the time loop.

Why It’s Cool
Because Bill Murray. Because Time Travel. Because the groundhog is always right but still drives angry.

THE WEDDING SINGER (1998)

Boy Meets Girl
Robbie, the wedding singer, makes friends with Julia at a wedding she’s catering. He invites her to his wedding, which goes south when the bride doesn’t show up. Julia desperately tries to combat Robbie’s suicidal depression, and love blossoms.

Boy Loses Girl
Problem is…Julia’s engaged. To a guy named Glenn Gulia. Glenn Gulia is a douche, and it’s when Robbie points this out, that he loses Julia’s friendship.

Boy Gets Girl Back
After giving up on the whole situation for a little while, Robbie is inspired, and pursues Julia. Culminating in a mid-flight serenade as she flies to her Vegas wedding with douchey Glenn, who is douchey. She is moved to tears. And love.

Why It’s Cool
Again, chemistry. Barrymore and Sandler, despite being an odd pairing, work really well together on screen. The over-the-top 80s setting adds to the comedy.

MEET THE PARENTS (2000)

Boy Meets Girl
Actually…they already met, and things are serious from the get-go. The movie opens with a montage of Greg Focker and Pam Byrnes falling in love, and in the first scene Greg is about to propose to Pam, but before he can he’s upstaged - Pam’s sister is getting married. Which means all the family is getting together, which mean Greg gets to meet Pam’s parents. Pam’s father Jack is a scary, scary man.

Boy Loses Girl
Over the course of the movie Greg, although he’s already got the girl, just can’t seem to do anything right. Everything he tries to do, he fails at. Sometime after desecrating the remains of Pam’s grandmother, breaking her sister’s nose, burning down that same sister’s alter, spray painting a cat, accusing his prospective father in-law of espionage and being exposed as a Gaylord Focker, the relationship is over.

Boy Gets Girl Back
Jack, after discovering his prospective son-in-law was a Gaylord and not a Greg, is proven to have been mistaken about his assumption that Greg was a liar. Sort of, seeing as how he lied about his name… Whatever, Jack rushes to the airport and Greg declares his love for Pam to Jack. He gets her back.

Why It’s Cool
Greg’s only real failing is that he tries too hard, he feels the weight of expectation, and instead of presenting himself honestly he presents himself the way that he feels he should. Everyone can relate to feeling intimidated and behaving out of character. And he doesn’t have to change at all to win the girl back, he was a nice guy all along.

SIDEWAYS (2004)

Boy Meets Girl
Miles (Paul Giamatti) is the very opposite of the traditional leading man in a romantic comedy, he’s a deeply depressed, irritable, balding, gnome-faced slouch who steals money from his mother and “goes to the dark side” when he’s drunk too much. On a road trip through Californian wine country to celebrate his friend Jack’s (Thomas Haden Church) upcoming wedding, Miles encounters Maya (Virginia Madsen) and they bond through a shared passion for wine and wine making.

Boy Loses Girl
Friend Jack starts boning Maya’s best friend. But Jack is getting married on Saturday. The secret slips out and Miles is held responsible.

Boy Gets Girl Back
After getting dumped, Miles finds his book has been rejected by publishers, gets chased by a naked man, has his car crashed into a tree, and discovers his cherished ex-wife is pregnant by her new man. Luckily he returns home to find a conciliatory answer phone message from Maya. She’s even read his unpublished book - both boxes of it.

Why It’s Cool
Beautiful sun-kissed scenery, great chemistry and a romance that focuses on middle aged men who have achieved next to nothing. It’s warm, funny, moving and never takes itself too seriously.

500 DAYS OF SUMMER (2009)

Boy Meets Girl
Summer is the new girl working for the greetings card company where Tom works, Tom digs her. She tells Tom she likes the music he’s listening to, and he falls in love with her. Simple as. Summer doesn’t believe in love, but Tom’s so into her, he agrees to have a more ‘casual’ relationship with her.

Boy Loses Girl
Casual doesn’t work out so well, what with Tom being so crazy in love he should feature Jay Z. Summer ends it because, well, because of the reasons she stated when they were getting into the relationship in the first place. Kind of out of the blue though, still…

Boy Gets Girl Back
Nope. 500 days, it’s in the title.

Why It’s Cool
It has style and substance, and it’s genuinely different in spite of hitting almost every note in the rom-com handbook. Impressive, and funny as hell.

What do you think are the top romantic comedies? Leave your thoughts in the comments.