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The 100 Best Romantic Comedies of All Time (Part One)

You've Got Mail (1998). Photo: Warner Bros
You’ve Got Mail (1998). Photo: Warner Bros


Romantic Comedies have become a bit of a downer as of late. In fact, it seems like a dying film genre. Critics rip them to shreds unless the filmmakers find ways to cross their story over into other genres deemed acceptable (and even then it “typically” only gets mediocre reviews). If the couple doesn’t end up together, then it has a higher chance of being critically accepted (500 Days of Summer). Or if the romantic male lead as a character is more realistic and looks like your average Joe, it also has a higher chance of being accepted (Knocked Up). Are the jokes cruder? The women more politically correct? Does the romantic comedy appeal to a male demographic?

These seem to be the checklist for many of the recent romantic comedies.

Now I’m not here to argue whether or not these films are good. That’s not my point. Rather, I’m here to argue in the favor of traditional romantic comedies that don’t have to cross over into so many other genres to actually get made. Don’t get me wrong, I’m all for genre crossing (you’ll definitely see a bunch on this list), but that doesn’t mean we shouldn’t also be able to create conventional romantic comedies as well.

Right now, let’s just say romantic comedies are no longer the popular kid in class!

And why is that? Fans of the genre are told that romantic films and fairy tales are bad for us. They make us long for unrealistic and completely unattainable relationships. I’m sure you’ve heard the arguments. So do people simply assume that we are too silly minded to understand the difference between fantasy and reality? Romantic Comedies are a subgenre of happily ever after fairytales, after all…

What then of action films clearly geared to a male demographic? What of the female characters in action films? I don’t know about you, but these women don’t seem particularly realistic. They have perfect bodies, perfect hair, they kickass like a ninja while also still needing the man to rescue them. Um….what?

Personally, I don’t watch a romantic comedy for realism. I’m pretty sure most people say the same thing about these action flicks I mentioned or the latest superhero blockbuster. Rather, I watch them because I think they’re entertaining. I like escapist romances. It’s a genre of film that deserves more respect than it actually gets. Take a look at all those really crappy romantic comedies out there, for instance. Proof it’s not so easy to pull one off.

So for this week’s Top List I thought it would be fun to celebrate great romantic comedies.

For my list, while some of the romantic comedies cross over into other genres (musical, situational comedy, action, fantasy and even dramedy), the films mainly focus on the romance between the main couple and the obstacles between them. Not only that, the film has to be funny. So there are some great romances out there, but that doesn’t necessarily mean they’re a romantic comedy. There is such a thing as a romantic drama!

What you won’t find are a few of the popular ones from the last few years because I think many of them are a new subgenre of romantic comedies that perhaps cross a little TOO far over into the stoner or crude comedy path driven more to a teenage male demographic.

In all, I tried to pick a variety of romantic comedies from classic to modern day that represent some of the best cinema history has to offer.

So without further ado, here are some of the best romantic comedies of all time. I’ll list the first 50 this week and the final 50 in the near future!

THE 100 BEST ROMANTIC COMEDIES OF ALL TIME PART I (in no particular order)

#1 You’ve Got Mail

Year: 1998

Director: Nora Ephron

Starring: Meg Ryan and Tom Hanks

My Take: Influenced by Pride and Prejudice (more of a romantic drama, so no adaptations made the list) and Shop Around the Corner, this tale of competing book lovers is the ultimate romantic comedy showing everyone how to do the genre right. It’s witty, entertaining and yes, romantic. Not to mention the perfect casting of Tom Hanks and Meg Ryan. If you want to be reminded of why romantic comedies are awesome, watch this memorable classic!

#2 It Happened One Night


Year: 1934

Director: Frank Capra

Starring: Clark Gable and Claudette Colbert

My Take: This is romantic comedy at its best (even winning some Oscars) as a spoiled young heiress runs away from home (or at least her father) to get to her “husband” in New York City. Along the way, she enlists the help of a reporter who wants the exclusive on her story. Of course, you can guess what happens next…

#3 Sleepless in Seattle

Year: 1993

Director: Nora Ephron

Starring: Tom Hanks and Meg Ryan

My Take: There’s something magical about the duo of Tom Hanks and Meg Ryan. Together they’re able to create movie magic. Sleepless in Seattle manages to pull off a clever, witty, romantic comedy without the two actually meeting until the end. Still, it remains one of the best classic romantic comedies of all time. It really is both incredibly romantic while also being incredibly funny. Plus, it’s nice to see two leads with such an amazing chemistry.

#4 While You Were Sleeping

Year: 1995

Director: Jon Turteltaub

Starring: Sandra Bullock and Bill Pullman

My Take: This movie really helped audiences fall in love with Sandra Bullock. If there’s one thing she’s great at, it’s the romantic comedy genre. She’s able to pull off the All American good girl charm with a combination of likability and vulnerability. And what makes me love this romantic comedy in particular is that ultimately it’s about loneliness. Lucy is such a real character and we root for her to find the happiness she deserves. Moreover, while Bill Pullman isn’t your typical leading man, he’s exactly right for the role. There’s nothing not to love about this film that has comedy, romance and even a little heartbreak.

#5 When Harry Met Sally

Year: 1989

Director: Rob Reiner

Starring: Meg Ryan and Billy Crystal

My Take: This may be one of the most popular romantic comedies…ever. While it’s not my personal favorite (I still really liked it), Nora Ephron proved time and time again that she was the queen of writing romantic comedies. This film asks the age old question: Can men and women ‘just’ be friends? Meg Ryan and Billy Crystal had a fun chemistry which worked well with the memorable script.

#6 Breakfast At Tiffany’s

Year: 1961

Director: Blake Edwards

Starring: Audrey Hepburn and George Peppard

My Take: Despite a few strange racist moments in the film, this movie is pure romantic comedy gold. It’s funny, classy and unforgettable. Plus, it’s Audrey Hepburn at her most memorable. Not to mention the music classic “Moon River” and the amazing kiss in the rain. What’s not to love?

#7 Notting Hill

Year: 1999

Director: Richard Curtis

Starring: Julia Roberts and Hugh Grant

My Take: This story of a movie star who falls in love with a bookshop owner, follows all the romantic comedy cliches, but somehow never feels tired or obvious. It’s filled with so much charm (in part thanks to the witty script) and sincerity that it’s hard not to love this film. It truly is one of the greatest romantic comedies of all time.

#8 Love Actually

Year: 2003

Director: Richard Curtis

Starring: Colin Firth, Keira Knightley, Bill Nighy, Emma Thompson, Hugh Grant, Liam Neeson, Andrew Lincoln, etc.

My Take: While I didn’t love “every” romance included in this film, for the most part, the interweaving story lines and love stories are simply entertaining. And who doesn’t love Colin Firth?

#9 Bridget Jones’s Diary


Year: 2001

Director: Sharon Maguire

Starring: Renee Zellweger, Colin Firth and Hugh Grant

My Take: There’s so many reasons to love this romantic comedy, I can’t even count. But here’s a few: One, Colin Firth makes a glorious return to his most beloved role as Mr. Darcy. Two, every time Hugh Grant enters the screen the film becomes hysterically funny. Three, Bridget Jones is pure awkwardness and hilarity as she finds herself in the most humiliating scrapes. And finally, it’s very romantic. Honestly, the film just gets funnier and funnier each time I watch.

#10 Pretty Woman

Year: 1990

Director: Garry Marshall

Starring: Richard Gere and Julia Roberts

My Take: A romantic comedy power duo, Gere and Roberts shined onscreen together in this Cinderella-esque fairy tale of a prostitute who finds love with a wealthy businessman.

#11 Runaway Bride

Year: 1999

Director: Garry Marshall

Starring: Julia Roberts and Richard Gere

My Take: What I love about Runaway Bride is that it is a pure, traditional romantic comedy and a great one at that. It doesn’t hurt that there’s a great chemistry between the leads of course either. The concept was fun, it had a great soundtrack, the supporting characters were funny, not to mention there was a real underlying substance here. Maggie as a character has some real flaws and problems. And it’s actually kind of sad how the people in her town treat her. And that’s something a lot of romantic comedies that fall short forget – you can’t just follow the formula of a romantic comedy and expect it to be good. The characters need to have some actual depth. And this one does it well in a very funny and entertaining way. Comedy is usually at its best when it’s capturing some real truth about humanity.

#12 Never Been Kissed


Year: 1999

Director: Raja Gosnell

Starring: Drew Barrymore and Michael Vartan

My Take: I don’t know about anyone else but I never had an English teacher that cute! This romantic comedy about an awkward undercover reporter who has never been kissed (and falls in love with the English teacher of the high school she’s undercover at) is charming and VERY romantic. Josie’s epic first kiss is one of the most amazing cinema kisses…ever.

#13 Miss Congeniality

Year: 2000

Director: Donald Petrie

Starring: Sandra Bullock and Benjamin Bratt

My Take: This is actually one of my personal favorites. It’s one of those movies you can watch over and over and still laugh every time. Plus, there was something dreamy about Benjamin Bratt as Gracie’s partner that made it easy to root for them. Not to mention their banter was just so much fun to watch. I like to pretend the sequel doesn’t exist.

#14 Amelie


Year: 2001

Director: Jean-Pierre Jeunet

Starring: Audrey Tautou and Mathieu Kassovitz

My Take: This movie is quirky, delightful, original and of course, romantic. This tale of a shy woman who spends her time helping others and finds love along the way is a charming story. There’s nothing else quite like Amelie and I can’t recommend it enough. It’s refreshing to watch a movie about a female character who is extremely introverted.

#15 Pillow Talk

Year: 1959

Director: Michael Gordon

Starring: Doris Day and Rock Hudson

My Take: This rom-com is hilarious from start to finish – and it doesn’t hurt that Day and Hudson are simply magical onscreen together. They really know how to play off each other well while playing up both the comedy and the romance. It’s the go to love/hate relationship that we can’t help but love.

#16 Bend it Like Beckham

Year: 2002

Director: Gurinder Chadha

Starring: Parminder Nagra and Jonathan Rhys Meyers

My Take: Bend it Like Beckham explores the idea of reaching for your dreams even if it doesn’t suit the interests of your parents. So while Jess pursues soccer secretly against the wishes of her family, she also falls in love with her very handsome coach who believes in her. I saw this movie in the theater twice and both times two different audiences gasped at the same time. The scene in question? When Joe (Jonathan Rhys Meyers) shows up at her doorstop to talk to her and turns around. It’s the first time we see him out of his coach uniform (or at least that’s what I remember) and he looks very different and very romantic. By that point, the audience knew where the story was going. Their love story is one for the books for sure.

#17 Return to Me

Year: 2000

Director:  Bonnie Hunt

Starring: David Duchovny and Minnie Driver

My Take: Return to Me is proof that one, Bonnie Hunt should direct more films. And two, that David Duchovny is the perfect leading man. Though I admit to only saying that (mostly) based on the mere fact that I want to marry Mulder. Kidding aside, this story is both tragic and funny. The first part of the film will have you in tears when Bob’s first wife tragically dies in an accident, only to laugh often in the next part when he falls unknowingly with the woman who received his wife’s heart in a transplant. This film is perfectly sweet without going into cheesy territory. It’s truly a wonderful film.

#18 Two Weeks Notice

Year: 2002

Director: Marc Lawrence

Starring: Sandra Bullock and Hugh Grant

My Take: This is one of those traditional romantic comedies that isn’t afraid to fully embrace what it is, which in this case really works in its favor. Bullock and Grant together are one of my favorite romantic comedy duos. Both of them are comedic geniuses, so when they come together it’s comedy at it’s best. Then throw in the romance and it’s romantic comedy at it’s best. Again, there’s something about Hugh Grant that puts me in stitches. And Sandra Bullock is always funny and always likable.

#19 The American President

Year: 1995

Director: Rob Reiner

Starring: Michael Douglas and Annette Bening

My Take: It’s a classic boy falls in love with girl story, you know except that the boy happens to be the President of the United States. With these two, sparks fly right from the start. The movie is romantic and funny with great storytelling to support what makes for a fantastic film.

#20 Harold and Maude

Year: 1971

Director: Hal Ashby

Starring: Ruth Gordon and Bud Cort

My Take: This may well be the strangest romantic comedy of them all. It’s dark and unusual about a young man obsessed with death who befriends and falls for a 79-year-old woman at a funeral. It’s a fabulous film everyone should check out.

By on March 4th, 2015

About Amber Topping

Amber works as a writer and digital publisher full-time and fell in love with stories and imagination at an early age. She has a Humanities and Film Degree from BYU, co-created The Silver Petticoat Review, contributed as a writer to various magazines, and has an MS in Publishing from Pace University, where she received the Publishing Award of Excellence and wrote her thesis on transmedia, Jane Austen, and the romance genre. Her ultimate dreams are publishing books, writing and producing movies, traveling around the world, and forming a creative village of talented storytellers trying to change the world through art.

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8 thoughts on “The 100 Best Romantic Comedies of All Time (Part One)”

  1. This list… so fun! Great introduction article; I love this line: “So do people simple assume that we are too silly minded to understand the difference between fantasy and reality?”

    Lots of favorites here including Penelope, Pretty Woman, The Holiday, Two Weeks Notice, Miss Congeniality, Never Been Kissed! Oh and I’ve been meaning to rent Silver Linings Playbook. Thanks for the reminder. 🙂

  2. I love your list so far! So many great movies. I especially love that you’ve included so many wonderful classics. I don’t know whether you’ll be including this one, but “Libeled Lady” is a really funny, clever screwball comedy from the 1930s and deserves to be in the top hundred.

    • Thanks! I wanted to grab a large variety. 🙂 And I love the classics! And no, I don’t have that one, mainly because I haven’t heard of it surprisingly. I will have to put it on my list to check out. I looked it up now and it sounds like a movie I would love!

  3. Nice, mostly flicks that any fan of the genre would have chosen with a few “dark horses”. the lady does have style.. Just a few thoughts. I’m sure you realize Diane Lane wasn’t the co-star of Annie Hall (-;/, personally, I’d have gone with the original Sabrina, Ormand is delightful, but not Audrey Hepburn and Bogie was better at stoic than Harrison Ford… though the remake still would make my own top 100. I’d like to read your work some day.

    • Thank you! I do realize. Thanks for pointing it out so I could fix. One of those brain relapses I think where you see something in your mind and it comes out differently! Haha. So it is now fixed. 🙂 Anyway, fair point about High Fidelity and Grosse Pointe Blank. I admit to never seeing either. Not sure why. I kind of had the two Sabrina’s at a tie. So the Bogie one is in part 2 at #51. I always liked them equally!


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