Top 10 Best Romantic Comedies Of All Time

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It’s Valentine’s Day, which means you’re allowed to watch romantic comedies without feeling too guilty. However, there are some genuine gems of the infamous genre, and these are the best of all: the top 10 best romantic comedies of all time.


10. Romantics Anonymous (2010)Emotifs Anonymes

We’ll start off the list with a wonderful little gem that you’ve likely never seen. A quirky French romantic comedy, running at only 80 minutes long, known as Romantics Anonymous (or Les émotifs anonymes).

It’s probably one of the most delightful films I’ve ever seen, and that’s simply because it’s so sweet and upbeat. Centring around two awkward people, who both work in a chocolate factory, the film is a beautifully quirky tale of their developing relationship.

Unlike most romantic comedies, Romantics Anonymous manages to portray a modern relationship in both a romantic, and entertaining way. The quirkiness of the film gives it a wonderful charm that is furthered by the excellent comedy throughout, and by the end, you’ll be both moved by the story, and laughing your socks off thanks to the jokes.


9. (500) Days Of Summer (2009)500 Days of Summer

(500) Days Of Summer is probably the most modern romantic comedy ever made, because of the way that it goes about the story in such an unorthodox way.

Following the up and downs of the relationship between Tom (Joseph Gordon-Levitt) and Summer (Zooey Deschanel), the story is told in a non-linear format, and it makes for fascinating watching, as the direct contrasts we see between Tom’s emotions at the happy and sad points of his relationship makes for even more powerful emotion.

It’s also famous for its hugely original ‘Reality vs. Expectations’ sequences. Instead of following the rom-com trend and just going for a Cinderella story, 500 Days Of Summer is brutally realistic on many occasions, as emphasised in those scenes.

However, don’t think it’s a complete downer. There are of course still loads of great laughs, and Gordon-Levitt and Deschanel’s performances are absolutely wonderful, but it’s the emotion that really prevails from this film. Do watch it, but bear in mind you’ll have to think a bit for this one, because it’s not a mindless genre film.


8. Waitress (2007)WAITRESS

At times a real-life drama, at times a hugely sweet and upbeat romance, Waitress is an absolutely fantastic film that features wonderful performances, an adorable story and hugely funny comedy.

Starring Keri Russell as a young woman, working as a waitress at a quaint little pie shop, who is pregnant with the child of her abusive boyfriend. It’s at times a little dark, but the film develops into her romance with her doctor, and from then on it’s absolute bliss.

The shots of the delicious pies are enough to sell you on watching Waitress, but don’t discount the fact that this is a hugely intelligent film as far as romantic comedies go. Whilst telling a nice story, it also deals with important real-life problems like domestic abuse and young pregnancy, and that’s what really sets it apart from the crowd. You’ll love watching Waitress, but remember that there’s more to it than just the quirky romance.


7. Man Up (2015)Man Up

Man Up is an example of the hugely formulaic romantic comedies that plague the 21st Century, yet it’s one of the very few that work like a charm.

A fast-paced, energetic comedy that’s filled with laughs from start to finish, Man Up is at times more exciting and thrilling than many action movies nowadays, particularly in its brilliant final act. Yes, it follows the romantic comedy formula very closely, but that brilliant comedy and the rapid pace mean that you can get completely caught up in the story and just go along and enjoy the ride.

But the real stand-out in Man Up is the performances. Simon Pegg and Lake Bell, stars of many an average rom-com, are excellent together. Their chemistry is absolutely stunning, and they’re both hugely funny to watch as they go through the normal ups and downs of a romantic comedy relationship. This is undoubtedly a formulaic film, but for once, it uses the formula to make a feel-good, funny and even exciting story that I absolutely adored.


6. Roman Holiday (1953)Roman Holiday

Audrey Hepburn, one of the queens of the classic romantic comedy, got her big break in 1953’s beloved Roman Holiday, alongside Gregory Peck.

It’s a delightful tale of a princess who wants to break out of her boring official lifestyle and experience the real world, and in the process, she meets a charming journalist who, whilst trying to get some exclusive information out of the young princess, begins to develop a very real bond with her.

Apart from the beautiful locations all around the Italian capital, Roman Holiday is a film that’s full of laughs from start to finish, particularly from Gregory Peck’s character. What’s more is that it isn’t just a bog-standard romantic comedy. Yes, there’s a romance there, but for the majority of the film, it doesn’t feel like it’s two people falling in love immediately, but instead developing a real friendship. Its positive and upbeat nature means you can smile all the way through, and Hepburn and Peck’s wonderful chemistry is just the icing on the cake.


5. Dan In Real Life (2007)Dan In Real Life

Dan In Real Life was the first romantic comedy that I really loved. It’s undoubtedly a normal genre film, but there’s something about it that is just infectiously delightful to me.

Following Steve Carell, who plays a middle-aged widow with three daughters, spending time with his family at a lakeside cabin, the film develops into an unlikely romance when he meets a mysterious woman, Juliette Binoche, at a local bookstore.

The thing with Dan In Real Life is that, whilst its story is ultimately predictable, its combination of hilarious comedy and surprisingly powerful emotion is amazing. Carell’s character is the centrepiece of it all, and as he hilariously bumbles his way through an awkward romance, he also manages to share a lot about his deeper feelings, something that most romantic comedies just fail to do.

Dan In Real Life is a realistic and emotional story, but its comedy never lets it get away from being a fun watch all the same, and that’s what makes it such a great watch amidst the flood of average rom-coms nowadays.


4. Breakfast At Tiffany’s (1961)Breakfast At Tiffany's

Loosely adapted from Truman Capote’s classic novel, 1961’s Breakfast At Tiffany’s is an absolute classic of the romantic comedy genre that’s been loved since the day it was released.

Audrey Hepburn plays young New York socialite Holly Golightly, living in an apartment building the floor below a young writer, Paul Varjak, played by George Peppard. In a way, Breakfast At Tiffany’s is a simple romantic comedy similar to many of Hepburn’s other films, but in reality, it’s far more interesting and dramatic than those lightweight romantic comedies.

Yes, it’s a lot of fun to watch, and Blake Edwards does a fantastic job at showing the debaucherous lifestyle of these socialites, but it’s the continual theme about belonging that’s most powerful. Despite Paul’s strong love for Holly, she refuses to get caught up in a romance, because she just doesn’t want to belong to anyone, creating a huge emotional dilemma as the film progresses. Breakfast At Tiffany’s is a delightful watch, but its intelligence is hugely impressive all the same, and that’s what makes it such a classic of the genre.


3. Bringing Up Baby (1938)Bringing Up Baby

The 1930s and 40s were filled to the brim with romantic comedies, but the best of all of them is surely 1938’s Bringing Up Baby, starring screen legends Katharine Hepburn and Cary Grant.

This is a film that’s just purely hilarious from start to finish. It does have some things to say about modern relationships at the time, but that’s pretty dated nowadays, so the main enjoyment you can get out of this film is from its comedy, but that comedy really is special.

Hepburn and Grant are hilarious together as the dysfunctional friends who eventually fall in love, and their brilliant sparring throughout makes for laughs every second. From the first scene to the bizarre final act, where a leopard goes on the run (not something you see in most romantic comedies), you’ll wet yourself laughing at Bringing Up Baby in a way that modern films just can’t make you do any more.


2. Annie Hall (1977)Annie Hall

The most acclaimed of all the films on this list Woody Allen’s Annie Hall, which actually won the Oscar for Best Picture in 1977, even beating Star Wars to the top prize.

And you can see why, because Annie Hall is one of the best-written movies ever made, showing off the best of the best from Woody Allen, whilst the on screen chemistry between the romantic leads Diane Keaton and Woody Allen is just as special.

Annie Hall is a really funny film, and unlike many of Woody Allen’s earlier works, this one isn’t dated at all. Beyond that, the characters are fascinating, and it tells a brilliantly interesting story about looser modern relationships that very few films had done before. And of course, this is also a genius piece of cinema, because Woody Allen’s character breaks the fourth wall on numerous occasions throughout to give you a deeper insight into the status of his relationship with Annie Hall, which is both funny and integral in making this such an engrossing film.

This is a film that you can watch as both a lightweight romantic comedy as well as a deeper commentary on relationships, but there are still always laughs to be had.


1. When Harry Met Sally… (1989)When Harry Met Sally

In the end, however, When Harry Met Sally is the ultimate romantic comedy. Funny, romantic, emotional and intelligent, it asks the question: ‘can men and women ever really be just friends?’, and it’s a hugely entertaining road to find the answer.

Billy Crystal and Meg Ryan star in the lead roles, and take you on a journey through their relationship, as they go through various partners, jobs and houses, yet always remain close friends. The two are infectiously loveable as Harry and Sally from start to finish, and even when their relationship isn’t at its best, they’re both so fantastic together that you believe every step of the story.

It’s an emotional film, but it doesn’t come without a heap of hilarious comedy. Much of the comic relief comes from the pair’s various arguments and disagreements, as well as the supporting players such as Carrie Fisher and Bruno Kirby, so you can have a good, fun time watching it too.

It’s the best romantic comedy of all time for two good reasons: It’s absolutely hilarious, and a realistic, emotional tale that you’ll fall completely in love with.

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About Author

The Mad Movie Man, AKA Anthony Cullen, writes articles and reviews about movies and the world of cinema. Since January 1st, 2013, he has watched and reviewed a movie every day. This is the blog dedicated to the project: www.madmovieman.com

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