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What Are The Best Romantic Comedy Films Ever Made?

Updated on August 5, 2020
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I have a BA in history and creative writing and an MA in history. I enjoy politics, movies, television, poker, video games, and trivia.

Let's Look at the Top 10 Romantic Comedy Films of All-Time

Since I'm a guy, maybe I'm not the most qualified to select the top ten romantic comedy films of all-time. I think that such a list would be different depending on whether a man or a woman did the selecting. Still, what do I think makes a film worthy of the top ten designation in the romantic comedy category? Well, this is a great comedy film, not just a great romantic comedy film. Some films that are romantic comedies try too hard. I think the films that qualify for consideration as a top ten romantic comedy do so because the romance part comes so easily to them. See if you agree.

10. Roxanne

Year of Release: 1987

Director: Fred Schepisi

Great Line:

C.D. Bales: I, uh, notice you don't have any tattoos. I think that's a wise choice. I don't think Jackie Onassis would've gone as far if she'd have had an anchor on her arm.

Why is it a top 10 film: I guess that every time I see this title I can't help but think of The Police song. That being said, Steve Martin does an amazing job of conveying that sense that all people fear of being ugly on the outside or of people seeing them a certain way and hoping desperately that the object of affection will be able to see what's on the inside. This film has the perfect story to convey that point as Martin's character woos Daryl Hannah's character on behalf of a good looking guy with no personality. Of course, when Hannah finds out, it's Martin she wants once she sees past the nose. Based cleverly on Cyrano de Bergerac.

9. Sleepless in Seattle

Year of Release: 1993

Director: Nora Ephron

Great Line:

Dennis Reed: Annie, when you're attracted to someone, it just means that your subconscious is attracted to their subconscious, subconsciously. So what we think of as fate is just two neuroses knowing that they are a perfect match.

Why is it a top 10 film: I've got to admit that there's part of me that wanted to get turned off seeing Meg Ryan appear in one romantic comedy after another and thinking that after "When Harry Met Sally" she should have moved on. But when the screenwriter of that previous film tells you she's got another script that she's going to direct, it's probably hard to turn down. Sure, there's a bit of repetition in the whole thing, but some concepts are timeless. In this case, a little boy wants to find a wife for his lonely, widowed dad. The dad is played by Tom Hanks and across the country, Meg Ryan hears his voice and suddenly it's love at first hear. And isn't that the way it is nowadays? We hear a voice or see a picture. Meeting in person is practically an afterthought. Yet isn't that what we all hope for - meeting that perfect person without actually doing much other than pouring out our soul?

8. Groundhog Day

Year of Release: 1993

Director: Harold Ramis

Great Line:

Phil: I don't deserve someone like you. But If I ever could, I swear I would love you for the rest of my life.

Why is it a top 10 film: I'm not sure I have always thought of "Groundhog Day" as a romantic comedy. I have always thought of it as a Bill Murray movie. However, the movie is really about, among other things, the transformation Murray's character has to go through in order to get Andie MacDowell's character. And by get, I simply mean, convince her that he's sincere. Murray starts out as somebody who takes everyone, including himself, for granted, and doesn't particularly enjoy life. It is only through the process of repeating the same day over and over again - and going through every psychological state known to man - that he learns to appreciate life and express himself sincerely, honestly, and in a way that other people enjoy. Watching a man change from selfish to selfless to both love and be loved is as romantic as it gets. It's also hysterically funny as well.

7. When Harry Met Sally

Year of Release: 1989

Director: Rob Reiner

Great Line:

Harry Burns: I came here tonight because when you realize you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible.

Why is it a top 10 film: "I'll have what she's having" - I think that's what everyone can quote from "When Harry Met Sally". This film came out during my senior year in college and I think that basic premise espoused by Billy Crystal's Harry that men and women can't be friends because sex always gets in the way was the honest line that sucked men into this film because, really, Harry is speaking for all men. This film was yet another example of the greatness of Rob Reiner, which is somewhat under-appreciated. The guy has directed "The Princess Bride", "When Harry Met Sally", "This is Spinal Tap", and "Stand By Me", to really name a few, and isn't mentioned among the greatest directors of all-time. I think that's probably due to the general belief that comedy is easier than drama (though "Stand By Me" obviously isn't a comedy). He's known as a comedy director and it equals a lack of respect.

6. Annie Hall

Year of Release: 1977

Director: Woody Allen

Great Line:

Alvy Singer: A relationship, I think, is like a shark. You know? It has to constantly move forward or it dies. And I think what we got on our hands is a dead shark.

Why is it a top 10 film: Maybe it's because I haven't seen "Annie Hall" in awhile. Maybe it's because I'm a huge Woody Allen fan and appreciate his other films more. Anyway, I don't usually think of "Annie Hall" when I think of his best films, yet I know that it's one of the best. I like "Sleeper" better and "Crimes and Misdemeanors" too. Of course, I recognize the greatness of "Annie Hall". Often, Woody Allen's romantic films are for real people. Anxiety is his cornerstone.

5. The Apartment

Year of Release: 1960

Director: Billy Wilder

Great Line:

C.C. Baxter: Ya know, I used to live like Robinson Crusoe; I mean, shipwrecked among 8 million people. And then one day I saw a footprint in the sand, and there you were.

Why is it a top 10 film: Anybody who hasn't seen a Billy Wilder film doesn't know what they're missing. He's one of the all-time greats, having made "Double Indemnity", "Sunset Blvd.", "Stalag 17", and "Some Like It Hot" among many others. Those unfamiliar with him could see anyone of those films and likely be instantly hooked. Likewise, those who only know Shirley MacLaine as the ditzy actress who talks about past lives would do well to watch this film and see what a beauty and what a great actress she is and was.

4. Amelie

Year of Release: 2001

Director: Jean-Pierre Jeunet

Great Line:

Amelie: It's better to help people than garden gnomes.

Why is it a top 10 film: For those who saw "Amelie" in the theater when it was released, it was a revelation. It was a movie about this incredibly sweet woman and it had this cartoonish feel to it that was so original. But at its heart is this wonderful heroine who grows up lacking affection and finds joy in making others happy. It's really in watching her devote herself to making others happy that we get so attached to her because we realize the one thing lacking in her life is that affection from somewhere else. Sure, it's a fantasy, but it's touching and wonderful.

3. High Fidelity

Year of Release: 2000

Director: Stephen Frears

Great Line:

Rob: Sometimes I got so bored of trying to touch her breast that I would try to touch her between her legs. It was like trying to borrow a dollar, getting turned down, and asking for 50 grand instead.

Why is it a top 10 film: I don't think most fans of this film would immediately think of it as a romantic comedy, yet when you start thinking more about what drives John Cusack's character, you realize it is. The movie is about his quest for the truth of his love life. After breaking up with his latest girlfriend, Cusack's character takes stock of his past relationships and really examines things. I think that what keeps us from remembering "High Fidelity" as a great romantic comedy is that it's also a great comedy.

2. The Princess Bride

Year of Release: 1987

Director: Rob Reiner

Great Line:

Inigo Montoya: Hello. My name is Inigo Montoya. You killed my father. Prepare to die.

Why is it a top 10 film: I have no idea how I missed this film in the theaters. I have no idea how this film had such a short run in the theaters either. How does a film like this just not find an audience while in the theaters? According to records, it grossed somewhere between twenty-two and thirty million dollars. How is that possible? All I can think is that the film really had no major stars. Both Robin Wright and Cary Elwes were unknowns at the time and although it had great cameos, there just wasn't enough star power to draw audiences in. Looking back, it's hard to imagine. This is one of my favorite films of all-time.

1. Roman Holiday

Year of Release: 1953

Director: William Wyler

Great Line:

Princess Ann: I've never been alone with a man before, even with my dress on. With my dress off, it's MOST unusual.

Why is it a top 10 film: This was the film that made Audrey Hepburn a star. Combine Hepburn with somebody like Gregory Peck and you have the recipe for a great romantic comedy. Given the other films on this list, "Roman Holiday" is a classic, old-fashioned Hollywood romantic comedy. While there are aspects to this movie (the ending) that aren't entirely traditional, there is something about the innocence and sweetness of the film that are hard to resist. In fact, the film's entire story plays into the old fashioned sensibility since Hepburn is playing a princess who finds herself in the real world unbeknownst to anyone else. She's a character for whom the trappings of everyday life are completely foreign. Consider a recent film like "Monte Carlo" where the opposite is true. Hey, I'm a guy who almost put "Knocked Up" on this list, so I appreciate crass, but there really is something wonderful about a classic comedy that works because of great writing and great acting and a bit of innocence.

What is your favorite romantic comedy?

See results

This content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.

© 2011 Allen Donald


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