The Best Romantic Comedies of All Time?

Bringing together two heavyweights of romantic comedy, Hugh Grant and Julia Roberts, was a stroke of brilliance. Notting Hill is a modern-day fairytale of a Hollywood A-lister falling for a very ordinary bookshop owner. Roberts is brilliant as the famous actress battling the glitz of Hollywood, the pressure from the paparazzi, and her desire for the simple pleasures in life. Grant is as charming as always, with his puppy-dog eyes, sincerity, wit, and awkwardness as he tries to impress this woman he has only ever seen on billboards. With such memorable lines as “I’m just a girl, standing in front of a boy, asking him to love her,” and a loveable--if quirky--supporting cast, Notting Hill has us laughing while reaching for the box of tissues.

Can a man and woman just be friends? When Harry Met Sally tries to answer this question through the 12-year relationship between two acquaintances, played by Meg Ryan and Billy Crystal. From the drive to New York City, the bookshop encounter, and a New Years Eve declaration of love, the characters discuss their differing views on relationships. The chemistry between Ryan and Crystal is undeniable. And who can forget the infamous scene in Katz Deli? When Harry Met Sally made us all say “I’ll have what she’s having.”

Nicholas Cage would never be the obvious choice to play a romantic lead, but in Moonstruck it somehow works. Cher plays a superstitious Italian-American widow set to marry her current boyfriend. While he’s out of town, along comes her fiance’s one-handed, opera-loving, younger brother, played by Cage. With two lead characters that fit together so well, Moonstruck tells us that it’s sometimes OK to fall for Mr. Wrong.

The 1930s was an era when the movie industry discouraged “excessive passion,” but risque language was still permitted. The result was the 5 Oscar-winning It Happened One Night, a movie that oozes sexiness and lust without actually showing anything remotely erotic. Spoilt heiress Claudette Colbert and rooky journalist, Clark Gable set out on a long and crazy road trip, where they spar and match witty remarks before madly falling in love. It Happened One Night became the template for the classic rom-com – a couple who bicker so much they should really just shut up and kiss.

Thanks to his manipulative 8-year old son, widower Tom Hanks gets a second chance at love through a radio show. Meg Ryan forms an obsession with Mr. Sleepless in Seattle and manages to track him down using her journalistic skills. Living at opposite ends of the country, the two never actually meet until the very end of the movie. Even though Ryan is a little like a stalker, you can’t help but wait for the moment they come together.

Tom and Meg make a great rom-com couple, so it’s a close competition as to whether Sleepless in Seattle or You’ve Got Mail is the best. However, Sleepless in Seattle edges it slightly in the beautiful way it gives hope of finding love again, even after total heartbreak.

Audrey Hepburn as Holly Golightly is one of the most iconic characters in movie history, with her high chignon hair and oversized cigarette holder. Hepburn’s portrayal of the naive, slightly eccentric, society girl is matched brilliantly by George Peppard as he tries to tame the woman who never wants to work for a living. The actors' enchanting chemistry, combined with a soundtrack that includes Moon River, set Breakfast at Tiffany’s to be a winning rom-com.

This modern-day interpretation of Shakespeare’s Taming of the Shrew is the perfect high-school rom-com. Julia Stiles plays a tough and angsty teenager whose younger sister can’t go on a date until she does. Enter charming Heath Ledger, who’s paid to tame the heart of this wild-child. The storyline tackles high-school power dynamics, the frustrations of first love, and the cruelties of teenage heartbreak. 10 Things I Hate About You made stars out of newcomers Stiles and Ledger and, even now, their on-screen connection still sets hearts aflutter.

Love can happen at any age, as Jack Nicholson and Diane Keaton prove in Something’s Gotta Give. Aging womanizer Nicholson is dating Keaton’s thirty-something daughter when they meet at her family’s beach house. After a heart attack, Nicholson is prescribed rest and has to stay on at the beach house. As they spend time together, he finds himself falling for Keaton, and it’s a pleasure to watch romance blossom between them. Something’s Gotta Give shows us it’s never too late to fall in love.

Kate Hudson and Matthew McConaughey play two successful, beautiful people that come together with different 10-day missions--he has to get her to fall in love with him, and she has to get him to dump her. The result is a battle of the sexes that sees Hudson dragging McConaughey to a Celine Dion concert, embarrassing him at his poker night, and giving him a love fern to represent their relationship. No one can deny the on-screen chemistry between McConaughey and Hudson. How to Lose a Guy in 10 Days is a funny, romantic, sexy movie where you can’t help but cheer when this pair finally kiss and make up.

Julia Roberts was just twenty-one when she played the street worker who gets picked up one night by lonely businessman Richard Gere. After a night of drinking champagne, eating strawberries, watching I Love Lucy, and an ensuing moment of passion, Gere makes a $3,000 proposal Roberts can’t turn down. They spend the following week transforming--Roberts into a lady, and Gere into a man who realizes life is about more than just money. Pretty Woman is the ultimate Cinderella story where the working girl eventually gets her Prince Charming.