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Best Romantic Comedies

Updated on January 5, 2015

We want our heroes to get together, but secretly we don't want it to happen too fast...often the anticipation is much juicier than the actual fruit. The right balance of chemistry and tension in romantic comedies often can transform a good script into a great movie. When executed well, the romantic comedy film is a captivating genre that tugs at our emotions while tickling our funny bone.

The best romantic comedies have a rare mix of comedy, chemistry and tension. There has been some amazing on screen chemistry over the years, such as the chemistry between Cary Grant and Katherine Hepburn, William Powell and Myrna Loy and more recently Billy Crystal and Meg Ryan.

Romantic comedies can take many different forms. In some of my favorite romcoms, our heroes are thrown together by chance such as in films like Four Weddings and a Funeral and It Happened One Night. In others, one of the lovers, or an outsider, schemes to get the pair together such as in Bringing up Baby and The Philadelphia Story. And of course one of the age-old romantic comedy formulas has lifelong friends figuring out that they are really meant for each other as lovers, such as the film When Harry met Sally.

Whichever formula is used, the best romcoms will have us crying one moment and laughing the next. They endure in our memories long after we leave the theater and they give us a model for the relationships we seek to build in our own lives.

If you still have not satiated your desires for romcoms, you might check out our other lens on the Greatest Chick Flicks of all time and and the Best Julia Roberts Movies.

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10. It Happened One Night (1934)

Gable and Colbert find Romance on the Open Road

It Happened One Night won the Best Picture Oscar in 1934 largely because of the fantastic chemistry between Clark Gable and Claudette Colbert. This romantic comedy is one in a long line of brilliant Frank Capra films with endearing characters and believable backdrops.

Colbert plays Ellie, a pampered socialite who marries a man without her father's blessing. Her father has the wedding annulled and drags Ellie back home against her will. When she escapes, Ellie meets up with Peter Warne (Gable), a newspaperman, who agrees to help her cross the country back to her husband in exchange for a story. However along the way, Ellie and Peter develop a passion of their own ultimately falling in love.

This is a classic film and truly one of the greatest romantic comedies of all time.

If you liked It Happened One Night, you might also want to check out His Girl Friday starring Cary Grant and Rosalind Russell and Adam's Rib featuring Spencer Tracy and Katherine Hepburn. Both films are classic romantic comedies that provide a glimpse into Hollywood's glamorous past.

9. Roman Holiday (1953)

Audrey Hepburn is Delightful as Princess Ann

Audrey Hepburn is as lovely and charming as ever in this outstanding romantic comedy. While in Rome on a European tour, Princess Ann (Audrey Hepburn) fakes an illness to sneak out for a day of anonymous fun. However, an American reporter, Joe Bradley (Gregory Peck), recognizes the Princess and closes in for an exclusive. He offers to chaperone her around the town without letting on that he know who she is. Naturally the two fall for each other but along the way there is a lot of good comedic fun.

Few women, if any, had the charming screen presence of Audrey Hepburn. You may not think of Gregory Peck for comedic roles but he does quite admirably in this romantic comedy. The film was nominated for 10 Academy Awards and won 3, including the well deserved Best Actress Oscar for Hepburn. The film has been quite influential and you will see shade of it in many of the romcoms that followed.

This is one of the best romantic comedies of all time and an absolutely must see movie for the whole family.

If you liked Roman Holiday, then you need to see Breakfast at Tiffany's

Original Movie Trailer for Roman Holiday - Check out the movie preview for this delightful romantic comedy

8. You've Got Mail (1998)

Hank and Ryan Together Again in this Romcom

Tom Hanks and Meg Ryan created great on-screen chemistry in the 1993 blockbuster romantic comedy film, Sleepless in Seattle. Nora Ephron, who directed both films, went back to the well in You've Got Mail to bring Hanks and Ryan together again in this romantic film. While many think of Julia Roberts as the queen of modern romantic comedies, credit really needs to go out to Meg Ryan, who has been in three of the best romantic comedies of our generation, When Harry met Sally, the aforementioned "Seattle" and this film.

Joe Fox (Hanks) runs a bookstore chain that is on the rampage driving small "mom & pop" bookstores out of business. He meets Kathleen Kelly (Ryan) online and they fall for each other. Of course, at the time he does not realize that Kelly is the owner of a small bookstore squarely in his destructive path. The name is a reference to the alert sound that people received when getting email as an America Online (AOL) customer. The film came out at the height of online dating services and before AOL's long, drawn-out demise.

However, what is most ironic about this film is that the ultimate enemy of bookstores was not the bookstore chains, rather both large and small bookstores have been driven nearly into extinction by internet-based services (Amazon and ebooks) -- the same place that these two lovers supposedly meet.

It is a charming romantic film and Hanks and Ryan are once again wonderful together.

If you loved You've Got Mail, then you have to check out their original pairing in Sleepless in Seattle. It is a better story and one of the most charming romantic comedies of the past 30 years.

7. Roxanne (1987)

One of Martin's Best Comedy Films

Roxanne is a modern-day rendition of the Edmond Rostand play, Cyrano de Bergerac, written in 1897. Steve Martin plays the lead, CD "Charlie" Bales, whose oversized nose can't diminish is beloved spirit. While trying to help a "simple" friend romance Roxanne (Daryl Hannah), a beautiful newcomer to town, Bales falls in love with Roxanne himself.

While Martin historically had been best known for slapstick humor, he brought a sophistication to this role that endures as one of the best examples of the romantic comedy genre. Martin is able to convey both a happy-go-luck spirit while also demonstrating the anguish of unrequited love. Martin's role in Roxanne really demonstrated his comedic ability and led to a string of sophisticated comedy movie blockbusters.

If you are a Roxanne fan, they I would highly recommend you check out Four Weddings and a Funeral. It is another sophisticated romantic comedy starring Hugh Grant and Andie McDowell.

6. (500) Days of Summer (2009)

He Gets the Girl, then Loses Her, then...

Critically acclaimed as one of the best films of 2009, (500) Days of Summer is an interesting play on words on a short-lived relationship between Tom Hansen (joseph Gordon-Levitt) and Summer Finn (Zooey Deschanel). In the same vein as Annie Hall, (500) Days follows the short-lived relationship that end with both Tom and Summer in relationships with other people.

This romantic comedy uses a non-linear narrative that adds mystery to the storyline and Deschanel convincingly portrays a "free spirit" as she has in several other romantic comedies. The film also boasts an excellent soundtrack with an eclectic mix of old and new music.

If you liked (500) Days of Summer, you might also like Yes Man and Chasing Amy. Both are quirky romcoms with interesting characters and funny situations relevant to today.

Get Great Classic Couples Comedy from TV

Moonlighting - Seasons 1 & 2
Moonlighting - Seasons 1 & 2
Bruce Willis and Sybil Shepard had great chemistry and these old episodes will make you laugh til you cry
Bringing up Baby romantic comedy cary grant hepburn
Bringing up Baby romantic comedy cary grant hepburn

5. Bringing up Baby (1938)

A Classic for the Ages

If I had to select one actor that best epitomized the male role in romantic comedies, it would have to be Cary Grant. His sophistication and self-deprecating humor was so "comfortable" that is a joy to watch. Luckily, he left us with a huge library of great films and one of my favorite comedies is Bringing up Baby. Grant and co-star Katherine Hepburn are delicious together.

David Huxley (Grant) is an engaged paleontologist who meets Susan Vance (Hepburn) "by chance" on a golf course. Vance gets Huxley into a series of screwball travails. Grant plays the straight man to Hepburn's crazy persona, with a very unique sense of logic, and the interplay between them is hilarious. Surprisingly the film was a box-office failure, but endures today as a one of the best romantic comedys on many critics' all time favorite lists.

If you liked Bringing up Baby, then you have to see my favorite Romcom, The Philadelphia Story

Original Movie Preview of Bringing up Baby - Watch the trailer from one of the most best romantic comedies ever

4. Pretty Woman (1990)

Julia Roberts Establishes herself as the Queen of Romantic Comedy

Pretty Woman is one of the highest grossing romantic comedies of all time with an estimated worldwide box office of $460 million. What's not to love about this cute 1990s movie; Garry Marshall directs while Richard Gere and America's sweetheart, Julia Roberts develop great romantic chemistry. In addition to its box office success, Pretty Woman is probably one of the most replayed movies on cable television and may be the most viewed romantic comedy of all time.

It is the story of Edward Lewis (Gere), a successful corporate raider, who hires prostitute Vivian Ward (Roberts), to be his escort for for the week while he attends several important business and social events. Immediately, Lewis is intrigued by Vivian's personality and wit. She continually surprises him and as he puts it "people rarely surprise me anymore". Their professional relationship ultimately leads to romance and then love as he two get to know one another.

One of the unsung heroes of the film is the hotel manager, Barney Thompson (Hector Elizondo), who acts as a father figure in assisting Vivian in her Eliza Doolittle-esque transformation from prostitute to society gal. This is a difficult transition in believability and Hector provides the perfect blend of understanding and guidance to help us make this transition. Much like is role in the popular Princess Diaries movies, Hector creates a warm likable character that helps us better understand Vivian.

Popularity is sometimes a barometer of greatness and given its lasting earning power, Pretty Woman has to be considered one of the greatest romantic comedies of all time.

If you loved Pretty Woman, then you should also check out two of Julia Roberts other great romantic comedies, Mystic Pizza and Notting Hill. You will see why she is called America's Sweetheart.

3. High Fidelity (2000)

A Romantic Comedy for the Boys

High Fidelity is one of my favorite comedies of all time and serves as the best example of a bro-mantic comedy (e.g, romcom for men). Unlike most romantic comedies, it does not involve much interaction between the boy and girl but much more soul searching by the boy about the girl he lost and now wants back.

What makes this movie special is the brilliant verbal exchanges between the three male leads, Rob Gordon (John Cusack), Barry (Jack Black) and Dick (Todd Luiso) in Rob's record story. This movie launched Jack Black onto his comedic rise and is arguably his best film role. He is hilarious throughout and ends the movie with a big soulful singing performance. I can't remember how many times I have seen this film but there is always room for another viewing.

If you Loved High Fidelity, then you should also check out Say Anything

2. When Harry Met Sally (1989)

Crystal and Ryan Make Beautiful Music Together

When Harry met Sally may be the most copied romantic comedy in history. The 1989 film tells the story of two friends who remain simply friends over a 12 year period until they finally realize they might love each other and ultimately "get together".

The film explores the question, can a single man and a single woman actually be "just friends. It was groundbreaking in many ways and laid the foundation for many of the top romantic comedies that have followed.

It was a superb team led by Director, Rob Reiner, Billy Crystal as the boy and Meg Ryan as the girl. Carrie Fisher and Bruno Kirby also add excellent supporting roles. This film is the quintessential romantic comedy and a must see film.

If When Harry Met Sally is one of your favorite romantic comedies, then you should also check out Moonstruck starring Cher and Nicolas Cage. A quirky romcom, many consider it Cher's best work on the big screen.

1. Annie Hall (1977)

Allen and Keaton Start a Long String of Romantic Comedies Together

Annie Hall is arguably Woody Allen's best movie. It won four academy awards in 1977, including Best Picture. It is not a traditional romantic comedy because the boy does not end up with the girl in the end, but it is a great story about love and relationships.

The semi-autobiographical film follows the neurotic relationship between a comedian and a singer. After they break-up, Allen wants to reconcile and much of the film follows his memories of their tumultuous romantic relationship.

Ultimately, the pair agree meet on good terms and remain friends but the story behind the film is the give and take required to make any relationship work.

If you loved Annie Hall, then you should also check out Woody's other great romantic comedy, Manhattan. While many of Allen's films could loosely be construed as love stories, most are quite tragic. However, Manhattan is more classic romantic comedy that most.

Vote for the Greatest Romantic Comedies - So you love good romcoms, then you have to share your favs

romcom after the thin man
romcom after the thin man

Which of these top romantic comedies is the best?

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