The romantic comedy genre has evolved significantly across Hollywood’s history, with certain movies coming to represent a particular time and place. Whether it was black-and-white screwball comedies from bygone eras or contemporary explorations of the complexities of modern dating, the rom-com has remained an important barometer of our cultural landscape at any given time.

From meet-cute encounters that spearhead a whirlwind romance to more nuanced portrayals of the complexities of love, the romantic comedy genre includes some of the most beloved and thoughtful character studies ever captured on screen. While everyone will have a different favorite rom-com, these releases defined the genre.

10

It Happened One Night (1934)

It’s impossible to talk about the history of the romantic comedy genre without first giving credit to It Happened One Night. As Frank Capra’s extraordinary screwball love story, this tale of a pampered socialite falling for a roguish reporter has commonly ranked among the greatest films of all time and is one of just three movies to win all five major categories at the Academy Awards.

Clark Gable’s performance was so influential that it even helped form the basis for Bugs Bunny, as the influence of It Happened One Night extends far beyond what anyone could have reasonably expected. As a heartfelt and funny love story that still holds up to this day, It Happened One Night encapsulated the rom-com in the pre-Code era.

9

Roman Holiday (1953)

As the breakout role for Audrey Hepburn, it’s difficult to think of an onscreen couple with more chemistry than her and Gregory Peck in Roman Holiday. With a fairytale premise about a runaway bride and an exciting romance in Rome, this undisputed classic was an escapist fantasy that was elevated by the depth of the characters at the center.

Roman Holiday featured an outstanding script co-written by Dalton Trumbo, and its bittersweet ending subverted audiences’ expectations during a time when rom-coms usually followed a predictable format. As a blueprint for later rom-coms set on one magical day, like Before Sunset, Roman Holiday was ahead of its time.

8

The Apartment (1960)

The Apartment stands out as a genre-defining rom-com because it went deeper than anything before it. Through a mix of comedy and social commentary, this story of a man unwittingly allowing his apartment to be used as the setting for an affair with a girl of his dreams was a grounded exploration of corporate culture, infidelity, and loneliness.

Jack Lemmon delivered perhaps the best performance of his entire career as Calvin Clifford, the lowly office worker whose vulnerability made him intensely likable. With melancholic undertones, The Apartment proved that rom-coms don’t always have to be upbeat and that real characters and believable situations make a film all the more effective.

7

Breakfast At Tiffany’s (1961)

As Holly Golightly, Audrey Hepburn portrayed one of the most instantly recognizable rom-com protagonists in movie history. With iconic imagery and an unmatched sense of style, this adaptation of Truman Capote’s classic novel has endured in the public consciousness like few things before it, as Hepburn’s little black dress and oversized sunglᴀsses have become shorthand for fashionable elegance.

While the racial insensitivities of Mickey Rooney’s portrayal of Mr. Yunioshi certainly don’t stand the test of time, almost everything else about Breakfast at Tiffany’s has become a touchstone of popular culture. The character of Holly was also emotionally complex and layered in a way that few female roles in Hollywood were at the time.

6

Annie Hall (1977)

While the decision to award Annie Hall the Best Picture Oscar over Star Wars remains controversial, few can deny the impact of this Woody Allen film. As a template for the modern rom-com, Annie Hall broke from traditional narrative structures to tell a complex tale of romance through flashbacks, asides, fantasy sequences, and even addressing the audience directly.

Annie Hall was unlike anything that came before it, as its emotional honesty, awkwardness, and neuroticism presented relationships as they actually were, instead of some polished Hollywood presentation. As a major influence on later releases like High Fidelity and 500 Days of Summer, the rom-com genre would look very different today without Annie Hall.

5

When Harry Met Sally… (1989)

The romantic comedy genre was revitalized in the late 1980s through When Harry Met Sally, a beloved comedy that tackled the controversial question: Can men really just be friends with women? While this shouldn’t be a controversial idea, there was plenty of humor, heart, and hope at the center of this tale of two people who can’t seem to stop running into each other.

When Harry Met Sally felt like a fresh take on rom-com tropes at the time, and it was elevated by the outstanding performances of Billy Crystal and Meg Ryan. Watching the story of two people who were clearly made for each other but just couldn’t admit it was riveting, and this hilarious romance has remained a fan favorite for decades.

4

Pretty Woman (1990)

Julia Roberts became America’s sweetheart overnight through her magnetic performance in Pretty Woman. While the story of a businessman falling in love with a Hollywood escort might not sound like the most poignant premise, the truth was that Roberts’ and Richard Gere’s committed performances turned this into a modern Cinderella story.

Pretty Woman was an unconventional romance that took the idea of opposites attract to its absolute extreme. With a catchy soundtrack, incredible chemistry between its leads, and a premise we hadn’t seen before, Pretty Woman surpᴀssed all expectations to become a major hit at the box office and a genre-defining rom-com.

3

Bridget Jones’s Diary (2001)

The challenges of being a woman in the 21st century were perfectly captured by Renée Zellweger’s performance in the beloved rom-com Bridget Jones’s Diary. As the perfect representation of a messy, single, 30-something woman trying to balance work and romance in the modern era, Zellweger helped transform Bridget into a bona fide pop culture icon.

Through a love triangle story highly influenced by Jane Austen’s Pride and Prejudice, Bridget Jones’s Diary combined timeless themes with modern concerns. As the inception point for an entire franchise, the legacy of Bridget Jones has endured, with the most recent installment being released in 2025.

2

My Big Fat Greek Wedding (2002)

The cultural clash of Greek tradition with American customs in My Big Fat Greek Wedding struck a chord with viewers worldwide. By exploring the complexities of a Greek-American woman dating a man outside her heritage, this hilarious sleeper hit managed to surpᴀss all expectations and become the highest-grossing rom-com ever in domestic history.

My Big Fat Greek Wedding touched on a topic that had previously gone unexplored in mainstream comedies, as writer and star Nia Vardalos imbued her script with autobiographical authenticity. With plenty of sequences that will have audiences nodding their heads in recognition, anyone who’s been in a multicultural romance will recognize the hilarity of My Big Fat Greek Wedding.

1

Crazy Rich Asians (2018)

With a predominantly East Asian cast, Crazy Rich Asians highlighted the changes in diversity and representation in Hollywood over the past several decades. As a mainstream comedy that addressed class and racial tensions, this hilarious rom-com explored the complexities of navigating Chinese-American heritage. Director Jon M. Chu proved that even culturally specific stories could be relatable for all viewers.

Crazy Rich Asians was also a rare rom-com in the modern era that managed to find huge success at the box office and highlighted there was still an appeтιтe for more lavish, high-production-value romances. As a fantastic adaptation of Kevin Kwan’s original novel, Crazy Rich Asians demonstrated just how far the rom-com genre has come in terms of representation.