10 Best Romantic Comedies of All Time!

by Jennifer Hall
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Tom Hanks and Meg Ryan in a scene from "You've Got Mail." (Photo by Getty Images)

Tom Hanks and Meg Ryan in a scene from “You’ve Got Mail.” (Photo by Getty Images)

Whether you’re looking for something to watch with your best girlfriends or a flick to cuddle with your boo. It can be difficult to find the perfect romantic comedy.

To discover the perfect blend of talented actors — that know how to utilize both physical and verbal comedy, witty dialogue, entertaining story-line, and most of all chemistry; can seem like an insurmountable challenge.

So, just in time for Valentine’s Day I’m up for the challenge of pulling together the top 10 romantic comedies of all time!

Make a note that this list consists only of romantic comedies. Fan favorites like Love Jones and The Notebook fall under the “romantic drama” category and are not included on this list.

10. Love Actually

British writer and director Richard Curtis makes his first appearance on my list for the 2003 comedy Love Actually. This festive holiday film features ten different stories with overlapping characters as they navigate life and love five weeks before Christmas. The film features an all-star British cast including Colin Firth, Bill Nighy, Emma Thompson, Liam Neeson, Alan Rickman, Keira Knightley, and long-time collaborator Hugh Grant.

9. Annie Hall

American romantic comedy, Annie Hall, is a thought-provoking character study about the nature of love. Co-written and directed by Woody Allen, the film was released in 1977 and follows Alvy Singer (Allen), a comedian trying to understand why his relationship with his ex-girlfriend, Annie Hall (Diane Keaton) didn’t work out. Overflowing with richly clever dialogue against a sweeping canvas of New York City, Annie Hall won the 1978 Academy Awards for Best Picture, Best Director, Best Original Screenplay, and Best Actress.

8. Four Weddings and a Funeral

This hilarious British romantic comedy features Hugh Grant as Charles, a man who meets the woman of his dreams at a wedding. He subsequently reunites with her over several weddings and a funeral. Released in 1994, Four Weddings and a Funeral, is the first of several popular films written by screenwriter Richard Curtis. Clever writing and a delightfully eccentric group of friends makes this adventurous comedy and instant romantic classic.

7. Coming to America

This 1988 comedy is so funny that at times you forget that at the core of this side-splitting adventure is a very simple love story — a man leaves his home in search of a bride. When Prince Akeem (Eddie Murphy) abandons his homeland of Zamunda for Queens, New York, he is swept away to a world of “golden arcs”, substandard living, greasy-haired snobs, and eventually love. Coming to America features Arsenio Hall, James Earl Jones, John Amos, Eriq La Salle, and an unforgettable appearance by Samuel L. Jackson. Murphy and Hall also play a number of different unforgettable roles in the film.

6. Sleepless in Seattle

In 1993 the success of this Tom Hanks and Meg Ryan vehicle swept the country. Directed and co-written by the late Nora Ephron, Sleepless in Seattle was inspired by the 1957 film An Affair to Remember. Garnering two Academy Award nominations, Sleepless in Seattle, was nominated for two Academy Awards.

5. Pretty Woman

Julia Roberts emerging in a beautiful red dress; Richard Gere quickly closing the jewelry box causing her to radiate with laughter; Roberts telling the sales girls that it was a “big mistake” turning her away on her previous visit. Pretty Woman is celebrated for its many iconic moments. Lauded as one of the most successful films in the romantic comedy genre, the 1990 release catapulted a young Julia Roberts into international stardom.

4. Notting Hill

Named after the quaint English town that it is set in, Notting Hill is a delicious 1999 British romantic comedy starring Hugh Grant and Julia Roberts. Penned by Four Weddings and a Funeral screenwriter Richard Curtis, the film follows Hugh Grant’s character, Will Thacker. An ordinary travel bookshop owner, Will embarks on a relationship with Hollywood star, Anna Scott, played by Julia Roberts. The dialogue is witty, the plot adorable, and like the mesmerizing supporting cast that Curtis created for Funeral, Notting Hill also features a lively hodge-podge of secondary characters.

3. My Best Friend’s Wedding

Julia Roberts running at top speed behind Dermot Mulroney; singing a Deon Warwick hit in a crowded restaurant; and Cameron Diaz belting out terrible karaoke. These are just a few of the finer moments in the 1997 comedy My Best Friend’s Wedding. Both critically and commercially successful, this is the perfect date movie or flick to check out with girlfriends. The timeless story easily makes it a romantic comedy classic.

2. You’ve Got Mail

Tom Hanks and Meg Ryan found love again in 1998’s You’ve Got Mail. The Sleepless in Seattle alumni were in familiar hands under the direction of Nora Ephron (Sleepless in Seattle, When Harry Met Sally). An updated adaptation of 1940’s The Shop Around the Corner, You’ve Got Mail utilizes the phenomenon of on-line social networking. Brilliantly composed by Nora and her sister Delia Ephron (The Sisterhood of the Traveling Pants) one of my favorite pieces of dialogue occurs when Hanks goes to visit Ryan while she’s sick. Apologizing for putting her out of business he says, “It wasn’t personal.” Displeased by his comment she responds “…What is that supposed to mean? I am so sick of that. All that means is that it wasn’t personal to you. But it was personal to me. It’s personal to a lot of people. What is so wrong with being personal anyway? …Whatever else anything is, it ought to begin by being personal.”

1. When Harry Met Sally

This is absolutely my favorite romantic comedy of all time. With brilliant one-liners like “I’ll have what she’s having” and coining such concepts as “high maintenance” and “low maintenance” girlfriends. Writer Nora Ephron, director Rob Reiner, along with actors Billy Crystal and Meg Ryan set the bar high when they teamed up for When Harry Met Sally. Released in 1989 to critical acclaim and huge box office success, this romantic tale asks the question that men and women are still trying to answer today, “Can men and women really are just friends?”

Did I miss your favorite? Let me know below!

There were several close calls to our top 10 list. Here are a few of the noteworthy contenders…

Breakfast at Tiffany’s (1961)

Roman Holiday (1953)

Waitress (2007)

Jerry Maguire (1996)

Friends With Benefits (2011)

He’s Just Not That into You (2009)

Bridget Jone’s Diary (2001)

The Best Man (1999)

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