• Cody James

Top 10 Romantic Comedies of All Time

Who doesn't love a Romantic Comedy?

You get all the elements of a great moving-going experience.

You laugh…

You cry…

You sit and ponder how Harry and Sally didn’t realize they were meant for each other all along…

The romantic comedy genre has been around since the beginning of “talkies” in the 1930s and as the years have evolved, so has the genre itself. We’ve seen the cliché story of boy meets girl, boy loses girl, boy gets girl back. But despite some of the slumps in the genre over the years, there is no denying that there is a long list of great love stories that provide both emotional and entertainment value.

As Valentine’s Day approaches, I’ve created a list of the Top 10 Romantic Comedies of All Time. Now, some of these films may be a little “unconventional” but one of the best things about Romantic comedies is that there is such a large repertoire of great films to pick from.

Here are the 10 must-see Romantic comedies to put you in the Valentine’s Day mood.


The Philadelphia Story (1940)

While films like It Happened One Night (1934) and Bringing Up Baby (1938) are considered to have introduced the romantic comedy genre to American cinemas, for me, The Philadelphia Story is the best example of a perfectly made romantic comedy during Hollywood’s golden age. It’s a story about multiple love triangles and actions of characters that while hard to comprehend is all the more made up due to a hilarious script and outstanding performances from some of Hollywood’s greatest stars like Katharine Hepburn, Cary Grant, and James Stewart.


Harold and Maude (1971)

Romantic comedies probably more than any genre can go the predictable route. But this dark comedy is the most unconventional love story you will ever see. The film tells the story of Harold, a teenager who is fascinated by death and has a very morbid view of the world. He encounters Maude, a 79-year-old woman (played brilliantly by Ruth Gordon) who shows him just how thrilling life can be. Harold and Maude is a film that plays with existentialism, satire, and unexpected romance and if you are a fan of dark comedies, this film is sure to entertain you.


Pretty Woman (1990)

If a reader were to make the argument that Pretty Woman is not a romance film, I don’t think I would have much of a case to defend. I mean, I’m sure in 1990, women watching this film would have loved to trade places with Julia Roberts and be flown on a private Jet and be taken to the Opera by millionaire Richard Gere or go on an unlimited shopping spree and be taken off into the sunset in a limo. But let’s be frank, this is a story about a wealthy playboy who pays a prostitute to be his arm candy for a week. Not very romantic in the logistical sense but Pretty Woman just oozes with charm and it remains a quintessential romantic comedy that catapulted Julia Roberts to America’s Sweetheart status.


My Best Friend’s Wedding (1997)

Speaking of America’s Sweetheart, here we have another Julia Roberts film that has stayed ingrained in our brains ever since that fabulous dinner party ensemble of “I Say A Little Prayer” led by Rupert Everett. What I really enjoy about My Best Friend’s Wedding is the fact that for the first time in her career, Julia Roberts isn’t playing the charming and loveable angel for once. In this film, she’s conniving and devious (but in the most entertaining way). And the film really plays on the fact that you never know what you’ve got until it’s gone. From the stylish opening credits of the Bride and Bridesmaids singing “Wishin’ and Hopin’” to Cameron Diaz’s cringeworthy karaoke performance, My Best Friend’s Wedding receives tens across the board.


As Good as It Gets (1997)

This film and its placement on my list might shock a few people because I don’t think many people think of As Good as It Gets as a film that revolves around romance. But if you watch this movie closely, you will find that this film has all the elements of a great love story. Jack Nicholson plays Melvin Udall, a famous writer with obsessive compulsive disorder who alienates everyone around him with his blunt and negative attitude. He goes to the same restaurant every day and is waited on by the same waitress who has her own set of personal problems and it’s not until she points out just how insensitive and horrifying of a person Melvin is, that he begins to change is daily compulsive habits and do whatever it takes to keep her in his life, but still maintaining his harsh and all too truthful attitude.

As Good as It Gets also has one of the most romantic lines ever in a film.

It hits you right in the gut because we as a viewer are supposed to be perplexed and angry with Melvin Udall but when he tells Helen Hunt’s character that she makes him want to be a better man, all that animosity quickly goes away. I think that is how love works for a lot of couples. You might be longing for as Helen Hunt’s character would say, “A normal boyfriend!” but those charming moments remind you that sometimes this is As Good as It Gets.


Moonstruck (1987)

"SNAP OUT OF IT!" Moonstruck features the one and only Cher as an Italian-American widow who after meeting her eccentric Fiancé’s brother (played by a very sexy Nicolas Cage) falls in love with him. While an 80s flick starring Cher should be enough to pull you in to the movie, Moonstruck features an all-star ensemble cast and the dysfunctional family drama throughout the film along with the questions and answers about why men chase women makes Moonstruck an instant classic.


10 Things I Hate About You (1999)

I could have easily changed this article to the Top 10 Best Teen Romantic Comedies of the nineties and would have had no problem creating the list as there are a lot to choose from. But the one that sticks out the most to me is this modern-day retelling of William Shakespeare’s The Taming of the Shrew. It all just works so well; the music, the comedy, the acting. You know who to root for in this movie and everyone who watches this film can identify with at least one of these characters. And that iconic scene of Heath Ledger (R.I.P.) crooning on the bleachers remains one the best moments of his career.


Annie Hall (1977)

Woody Allen had been writing and directing films for years, but it wasn’t until 1977’s romantic comedy Annie Hall that he began to be noticed worldwide for his unique way of creating a scene with emphasis on observational humor. The film is brilliantly written (It won 4 Academy Awards: Best Picture, Best Director, Best Original Screenplay, and Best Actress) and tells the story from the viewpoint of both it’s male and female counterparts. The role of quirky musician Annie Hall was written specifically for Diane Keaton and the chemistry between Keaton and Allen in this film is beyond any of the other work they did together. Annie Hall is very straightforward in its humor. The message of the film is that love is neurotic, and we are not always meant to be with who we think we are supposed to be with.


The Wedding Singer (1998)

Adam Sandler dominated the 90s with comedy classics like Billy Madison, Happy Gilmore, and The Waterboy. But his absolute best work is this late nineties comedy that takes place in 1985, The Wedding Singer. As if the setting isn’t enough to make this film a joy to watch, The Wedding Singer combines all the elements of a traditional Sandler film with unusual side characters and hysterical moments. Adam Sandler plays Robbie Hart, a musician who performs at small town weddings. After his fiancé doesn’t show up to his own wedding, he decides to give up his hopes for finding love until he meets waitress Julia, played by Drew Barrymore. The Wedding Singer is full of hilarious moments and also has a lot of romantic scenes to offer. And the connection between Adam Sandler and Drew Barrymore on screen is the kind of love you dream to find. Now, if only life could always be like an 80s movie with Billy Idol sitting beside us on a plane.


When Harry Met Sally… (1989)

When I think of the term “Romantic Comedy,” my mind instantly goes to Harry and Sally walking in the park discussing their views on relationships between men and women. Nora Ephron’s script to this 1989 comedy about two people who cross paths over the course of 12 years and develop a friendship that turns in to unexpected romance is one of the greatest screenplays ever written. The structure of the film is built on the idea that men and women cannot be friends because “the sex part always gets in the way.” Harry and Sally are very neurotic New Yorkers who both have different views of how relationships work and the interaction between the two characters is built on the charming chemistry between Meg Ryan and Billy Crystal. When Harry Met Sally… is told from the viewpoint of what seems like a Woody Allen film. Much of the humor is observational and we see characters who are so put together let themselves go. I mean, who could forget that iconic restaurant scene?

Throughout the film, we see multiple married couples talking to the camera telling the unique stories of how they met, and it all culminates with the story of Harry and Sally. When Harry Met Sally… is the quintessential romantic comedy.

What are your favorite romantic comedies?

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About the Administrator:

My name is Cody James. Welcome to my blog - Some Like It Hollywood!

Since I was a kid, movies have always been my virtual escape from reality.

I love ALL TYPES of films from every era and enjoy talking about them.

I currently host a movie review segment on 102.9 W4 Country in Ann Arbor, MI.

You can also follow my blog on Facebook, Instagram, and YouTube.

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