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Romantic Comedies - Top 10 Best Romantic Comedies

The romantic comedy has been around since the beginning of Hollywood, but the genre really began to explode in the late 1980s and early 1990s with several classic films that have since been watched and rewatched by more than one generation of loving fans. The happy-go-lucky world that these movies portray is one that is essentially attractive—after all, who among us isn’t hoping that everything turns out for the best someday? Here are just ten of the side-splitting and heart-thumping stories that this genre has to offer.

1. When Harry Met Sally… (1989)

One of the most highly critically-acclaimed romantic comedies of all time, When Harry Met Sally… is still a household name even after two decades. It tells the story of the two title characters, played by Billy Crystal and Meg Ryan, as they confront their feelings for each other and their own notions of friendship and love. The famous diner scene, in particular, is an iconic moment in American comedy that’s consistently had audiences rolling on the floor.

2. Breakfast at Tiffany’s (1961)

Based on a novella by Truman Capote, this movie stars the radiant Audrey Hepburn in what is probably her best-known role. As Holly Golightly, the bubbly socialite, she captured the hearts and souls of people around the world in a performance that is still beloved to this day. Somewhat less beloved is the infamous stereotyping that occurs in a small part of the film, which is often edited out nowadays whenever Breakfast at Tiffany’s is shown on television.

3. Pretty Woman (1990)

Pretty Woman was a huge hit and an instant classic when it first hit theaters, and remains one of the highest-grossing romantic comedies to date. It is known for its wide fan base as well as for launching actress Julia Roberts into superstardom. The story, often considered to be a modern-day fairy tale, exemplifies the “hooker with a heart of gold” archetype as it is used in modern cinema.

4. Love Actually (2003)

A great Christmas movie as well as a great romantic comedy, Love Actually features a stellar cast of British actors portraying a collection of endearing characters in several intertwined storylines. The movie is known for its humor, its witty banter, and most of all, its sweetness. This is a good one to watch with your significant other any time you’re feeling down!

5. Sleepless in Seattle (1993)

In some ways, Sleepless in Seattle is a film with a long Hollywood history; it was directly inspired by 1957’s An Affair to Remember, which in turn was based on a movie called Love Affair from 1939. Sleepless in Seattle stars Tom Hanks and Meg Ryan in a dual performance that has been an audience favorite since the film’s release. The message is essentially that true love is meant to be, no matter how far apart the lovers.

6. Shakespeare in Love (1998)

This Academy Award-winning comedy is tied into what is perhaps the most famous romantic story of all time, William Shakespeare’s Romeo and Juliet. The movie gives a fictional account of a young William Shakespeare (Joseph Fiennes) finding inspiration for the classic play in his love affair with a noblewoman (Gwyneth Paltrow).? There are numerous references to Shakespeare’s work throughout the film, both in dialogue and in circumstances.

7. Notting Hill (1999)

A romantic comedy starring the king and queen of the genre, Hugh Grant and Julia Roberts, Notting Hill solidified the place of writer Richard Curtis after the success of an earlier British film, Four Weddings and a Funeral. A smash hit that was popular with both critics and audiences, it tells a classic tale of love blossoming against all odds between a famous celebrity and an impoverished bookstore owner.

8. Say Anything… (1989)

Now a favorite movie about the trials and tribulations of all-American high schoolers, Say Anything… made writer/director Cameron Crowe’s career. It features a sweet story about two students who are opposites, but the hero’s determination to be with the woman he loves won’t let anything stand between them. The famous boombox scene is iconic even today, long after boomboxes themselves have gone out of fashion.

9. 10 Things I Hate About You (1999)

This present-day adaptation of William Shakespeare’s The Taming of the Shrew stars a young Heath Ledger, Joseph Gordon-Levitt, and Julia Stiles. Like the play, it is about two people with abrasive personalities who have trouble admitting how deeply in love they are. Unlike the play, it is also a send-up of the modern dating scene in American high schools.

10. Bridget Jones’s Diary (2001)

Based on the novel of the same name by British writer Helen Fielding, Bridget Jones’s Diary is famous for openly portraying the struggles of its awkward heroine, played by Renée Zellweger. Hugh Grant and Colin Firth also star as the two men in a love triangle with her. Although there were doubts early on that an American could play such a quintessentially British role, the movie has developed a huge fan base in both countries since its release.


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