While they were once referred to as screwball comedies, romantic comedies have been a staple of movies since the 1930s, with these tales of often mismatched couples finding love against all odds. These movies date back to Ancient Greek comedy, and many of the rom-coms today owe a debt to classic Greek plays and Shakespearean tales.

Two people meet each other and either find quick attraction, only to find obstacles in their way, or they go from enemies to lovers, as they have an instant dislike for each other, only to fall in love over time.

Both of these romance movie tropes offer drama and comedy to entertain anyone who loves romantic movies but prefers to laugh at the ridiculous nature of finding love in all the wrong places.

10

When Harry Met Sally… (1989)

Finding Love In Friendship

In an era of men and women looking to hook up, When Harry Met Sally… presented a very different story. This is a mostly platonic tale that asks whether men and women can truly live as friends, without the hint of romance ever creeping in and ruining things. Billy Crystal and Meg Ryan star in the story as friends who struggle to make it work.

Written by the brilliant Nora Ephron and directed by Rob Reiner, both actors turn in a masterclass performance as they struggle to remain friends when things start to make them wonder if they could be so much more. While they ultimately end up together, the best parts of the movie highlight the struggles of male-female friendships in the real world.

Ephron was nominated for an Oscar for Best Screenplay, while the film also received five Golden Globe nominations. The Library of Congress added When Harry Met Sally… to the National Film Registry in 2022.

9

Pretty Woman (1990)

A Hollywood Escort Falls In Love With A Client

Pretty Woman never had any right to work based on its premise, but what resulted was one of the most beloved romantic comedies of all time. Julia Roberts stars as Vivian Ward, a Hollywood escort. She ends up hired by a wealthy businessman named Edward (Richard Gere) to accompany him to several functions.

While staying with Edward during the week she works for him, the two begin to develop feelings for each other, although both realize this might not be the best thing for their lives. However, this is a romantic comedy, and the movie has its fairy-tale ending, which gives them both a happily-ever-after.

Pretty Woman made Julia Roberts Hollywood’s most profitable leading lady for several years, and it also earned her an Oscar nomination for Best Actress. Pretty Woman is instantly quotable and extremely enjoyable, making it a Hollywood romantic comedy that all others were judged against for almost a decade.

8

Crazy Rich Asians (2018)

A Woman Learns Her Boyfriend Is From An Extremely Wealthy Family

Crazy Rich Asians was a mᴀssive hit when it was released in 2018 because it told a smart, sweet, and funny story centered on Chinese-American culture that had been overlooked for too long. With a primarily Asian cast and crew involved, it told the stories from a cultural perspective that was highly respectful and accurate.

Rachel (Constance Wu) is a Chinese-American professor named Rachel who travels to Singapore to meet her boyfriend Nick’s (Henry Golding) family, only to be shocked when she learns they are one of the wealthiest families in the country. What follows is a cultural conflict, with Nick’s family largely disapproving of Rachel and the relationship.

The movie was a box office success, earning $239 million on a $30 million budget. It also received critical praise, with a 91% “Fresh” Rotten Tomatoes score. While the Oscars ignored it, Crazy Rich Asians did receive a Best Acting by an Ensemble Award from the National Board of Review.

7

His Girl Friday (1940)

A Newspaper Editor Tries To Hold Onto His Star Reporter & Ex-Wife

His Girl Friday stars Cary Grant as a newspaper editor named Walter Burns, whose ex-wife is also his top reporter, Hildy Johnson (Rosalind Russell). He is about to lose her to another man, and he asks her to cover a murder case with him before she leaves, so he can try to win her back. Known in that era as a screwball comedy, the film remains a masterpiece.

Directed by Howard Hawks, the movie was based on the 1928 play The Front Page, which had already been adapted in 1931 under the same тιтle. However, the play wasn’t a romantic comedy, and Hildy wasn’t a woman, so His Girl Friday made significant changes that made the film so great.

This was the movie that helped introduce the spontaneous and often overlapping dialogue that rom-coms became known for over the years. It remains known as one of the best romantic comedies ever made, and entered the National Film Registry in 1993.

6

Sleepless In Seattle (1993)

Tom Hanks & Meg Ryan’s Romantic Masterpiece

Tom Hanks and Meg Ryan were considered the perfect romantic comedy couple for many years. The movie that won over the most fans arrived in 1993 with Nora Ephron’s film Sleepless in Seattle. Hanks played a widow whose young son called onto a radio show and told his dad’s story, which became extremely popular with people.

Ryan plays a journalist who sets out to discover who this man is and meets him to write a story about him. Of course, as a romantic comedy, this involves the journalist meeting the subject of the story and the two falling in love with each other. The chemistry between the actors was spectacular, and the film was one of the highest-grossing of 1993.

The movie earned two Oscar nominations (Original Screenplay and Original Song) and is the film that allowed Ephron to go from writing rom-coms to directing her own. Hanks and Ryan eventually re-teamed for You’ve Got Mail.

5

It Happened One Night (1934)

One Of The Oldest Rom-Com Masterpieces

The movie that created the romantic comedy genre is It Happened One Night​.​ Directed by Frank Capra, one of Hollywood’s greatest directors of the Golden Age, it won over audiences at the time, starring Clark Gable and Claudette Colbert. A spoiled socialite tries to get out from under her father’s control and falls in love with a roguish reporter.

The movie might be the most successful romantic comedy of all time in terms of critical acclaim. It was one of only three films in history to sweep the major awards at the Oscars, winning Best Picture, Best Director, Best Screenplay, Best Actor, and Best Actress (the other two being The Silence of the Lambs and One Flew Over the Cuckoo’s Nest).

The Library of Congress also added It Happened One Night to the National Film Registry in 1993, and it was one of the last movies released before the restrictive Hays Code changed the rules on what could be in movies concerning romance.

4

Notting Hill (1999)

Hugh Grant & Julia Roberts’ Rom-Com Masterpiece

Years after Julia Roberts arrived on the scene with her masterful romantic comedy performance in Pretty Woman, she was still on top of the world and starred alongside Hugh Grant in the 1999 rom-com Notting Hill. In this film, Grant plays a bookstore owner who meets a famous actress played by Roberts, and the two fall in love.

This is the classic tale of a wealthy and famous person falling for a working-class person, and the trials and tribulations that come with it. Luckily, both Grant and Roberts had great chemistry and were able to carry the familiar trope to great heights. It remains one of the best British romantic comedies ever made and has earned recognition from the Golden Globes and BAFTAs.

3

Bridget Jones’s Diary (2001)

Renée Zellweger’s Rom-Com Masterpiece

Based on Helen Fielding’s novel of the same name, Bridget Jones’s Diary stars Renée Zellweger as a woman stuck in the middle of a love triangle between two men (Hugh Grant and Colin Firth). The story itself is a loose adaptation of Jane Austen’s Pride and Prejudice, and Firth’s (who starred in the 1995 adaptation of Austen’s story) character even shared the name, Mr. Darcy.

In the first movie, Zellweger plays the тιтular character, a 32-year-old British single woman who writes a diary explaining what she wants to happen in her life. However, when she meets two men who both fall in love with her, she realizes that sometimes her dreams can be more complicated when they start to come true.

There have been three Bridget Jones sequels to the romantic comedy, but the first remains a fan-favorite addition to the genre and one of the best romantic comedies of all time, as well as Zellweger’s most beloved role of her career.

2

Clueless (1995)

A Rom-Com Based On Jane Austen’s Emma

Clueless is a teen coming-of-age comedy, but it is also a sweet romantic comedy with a controversial slant. The romance comes between two siblings, although they are not actually related. Alicia Silverstone stars as Cher, a high school student obsessed with fashion who lives to do “good deeds” to help other people, even if they don’t really want it.

Clueless is based on Jane Austen’s Emma, with Cher and Emma sharing the quality of always trying to help others, but never knowing how to help themselves. The rom-com comes with Cher realizing she actually has an attraction to the son (Paul Rudd) of her father, Mel’s ex-wife, who stuck with Mel after the divorce.

Getting past that weirdness, Clueless is a sweet and heartwarming romantic comedy that made Silverstone a star and helped propel Rudd into bigger and better roles in his career. It also spawned a TV series and a line of books, and was celebrated in 2025 with a re-release to celebrate its 30th anniversary.

1

Say Anything… (1989)

Cameron Crowe’s Often Copied Romantic Comedy

While John Hughes was the master of the teen comedies in the 80s, his romantic comedies remain mostly problematic to watch today. However, there was one romantic comedy from the 80s that remains a true masterpiece, and it had nothing to do with Hughes. This was Cameron Crowe’s breakout movie, Say Anything…

John Cusack stars as a high school senior named Lloyd Dobler who is mostly an underachiever. However, when he falls for the sheltered valedictorian Diane Coury (Ione Skye), he has to prove why he deserves the chance to sate her. This is a case of opposites attract, and few movies have done it better.

Say Anything… also remains a romantic comedy that has been copied endlessly by lesser movies in the years since its release, especially the boombox scene outside her window.