The romantic comedy has always been an underrated genre. Rom-coms are often dismissed, but love stories told with humor can make for some of the best movies ever made in the hands of the right filmmakers. Over the years, the genre has suffered from well-worn tropes — some of which are pretty sexist — but as those tropes have become more easily identified and audiences have begun demanding more from rom-coms, the genre has evolved.
Rob Reiner’s 1989 hit a prime example of a perfect romantic comedy.
When Harry Met Sally (1989)
A rom-com is only as strong as its leads’ chemistry, and in When Harry Met Sally, Billy Crystal and Meg Ryan proved to be two of the most perfectly matched rom-com leads of all time. Ryan went on to regularly collaborate with Tom Hanks, but she should’ve done another movie with Crystal.
The situations in When Harry Met Sally ring true, thanks to director Rob Reiner and screenwriter Nora Ephron drawing scenes and ideas from their own lives.
Boomerang (1992)
In most of Eddie Murphy’s starring vehicles, the director gives him free rein to fill each scene with his unique comic energy. This results in hilarious movies, but it doesn’t always result in great stories.
The great thing about Boomerang is that Murphy’s character has a real arc and he’s forced to change. He stars as a womanizing executive who gets a taste of his own medicine when his new boss (Robin Givens) turns out to be a female version of himself.
Chasing Amy (1997)
After repeating what worked in Clerks with his sophomore feature Mallrats, Kevin Smith delved into trickier, more emotional subject matter with his third and arguably most mature movie.
Ben Affleck stars as a comic book writer who falls in love with a woman played by Joey Lauren Adams. He’s heartbroken to find out she’s gay. Chasing Amy deals with a lot of relatable issues, like the strain that a relationship can put on an existing friendship.
Love, Simon (2018)
The first movie from a major Hollywood studio to revolve around an LGBTQ+ teen romance, Love, Simon stars Nick Robinson as a closeted high schooler trying to figure out the identity of the classmate he’s fallen for online and fend off a blackmailer threatening to out him to the whole school.
In addition to being groundbreaking in of representation, Love, Simon is also a charming, well-crafted romantic comedy in its own right.
Four Weddings And A Funeral (1994)
Before Richard Curtis would helm such iconic romcoms as Notting Hill and Love, Actually, he set a very high bar for himself with the hysterical script for Four Weddings and a Funeral. Hugh Grant and Andie MacDowell lead a star-studded ensemble cast.
The movie perfectly captures that time as a young adult when everyone starts getting married and there’s a wedding to go to every couple of months.
Always Be My Maybe (2019)
Randall Park and Ali Wong star in the Netflix rom-com Always Be My Maybe as a pair of childhood sweethearts who reunite as adults when their lives haven’t panned out as they expected and they have to confront their lingering feelings for one another.
Wong had been a writer on Park’s sitcom Fresh Off the Boat for years before they teamed up to write, produce, and star in this movie. The director, Nahnatchka Khan, also worked on the show.
The Big Sick (2017)
Oscar-nominated screenwriters Emily V. Gordon and Kumail Nanjiani based the unique story of The Big Sick on their own relationship. Nanjiani plays himself as a standup comic trying to make it and Zoe Kazan plays Emily, a heckler he falls for.
When Emily slips into a coma after they have a big fight, Kumail has to go through the second-act falling-in-love stage of the rom-com alone. When she awakens, she hasn’t been through this change; she just re the fight.
She’s Gotta Have It (1986)
Spike Lee’s feature-length directorial debut She’s Gotta Have It stars Tracy Camilla Johns as Nola Darling, a single woman in New York who has to choose between three suitors with their own advantages and disadvantages.
Along with Jim Jarmusch’s Stranger Than Paradise, She’s Gotta Have It helped to revitalize American independent cinema in the mid-1980s.
Groundhog Day (1993)
Bill Murray stars in Groundhog Day as a weatherman named Phil Connors who’s sent on the worst assignment he can imagine: going to snowy Punxsutawney to cover the Groundhog Day festivities. A blizzard maroons him in Punxsutawney and he has to stay one more night than he expected. And then, he finds himself living the same day over and over again.
After having fun with the time loop and eventually trying to take his own life and finding that the time loop won’t let him, Phil falls for his producer, played by Andie MacDowell, and uses his eternal imprisonment to become a better person to win her over.
Roman Holiday (1953)
William Wyler’s Roman Holiday is recognized as one of the greatest movies ever made. Audrey Hepburn plays a princess and Gregory Peck plays a news reporter she falls for.
Princess Anne becomes disillusioned with the royal lifestyle and breaks away to lead a normal civilian life for a couple of days.
