Although the genre is popular year-round, Valentine's Day is the perfect time to reflect on some of the most memorable romantic comedies ever made. The formula is quite simple. A man or woman is either looking for love or has absolutely no interest in finding love. After a series of events, some hilarious and some heart-wrenching, the protagonist finds their happily ever after.
The idealistic idea of love is comforting to viewers. As real life throws curveballs and obstacles, there's safety in knowing that, for at least a couple of hours, everything will work out. Throughout film history, the genre has undergone some pretty big changes, but some things stayed the same.
'Modern Times' (1936)
Like silent film actors transitioning to talkies, the Little Tramp (Charlie Chaplin) struggles to adjust to an industrial world in Modern Times. As Chaplin's voice is heard on film for the first time, his well-known character is seen for the last time.
In a series of unfortunate events, the Tramp becomes unemployed, hospitalized, and jailed. As he loses yet another job, the main character meets Ellen (Paulette Goddard). She's down on her luck and living in poverty, as well. Together, the couple represents the many Americans struggling to get by in the Great Depression era.
'The Philadelphia Story' (1940)
Cary Grant, Katharine Hepburn, James Stewart, Ruth Hulsey... what a cast! As Tracy Lord (Hepburn) is preparing to get hitched after a failed first marriage, she ends up in a love square. The confused bride-to-be is unsure if she's in love with her fiancé, the reporter covering the socialite's nuptials, or her ex-husband.
The Philadelphia Story was nominated for Best Picture at the Academy Awards. Three out of four of the main actors were also nominated, with Stewart winning in the Best Actor category. Ready for a fun fact? Storylines involving extramarital affairs were not allowed at the time. This film is known as one of the best in the "comedy of remarriage" subgenre. It allows for some flirtation and romance among the divorced characters before the couple inevitably reunites in the end.
'Singin' in the Rain' (1952)
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Speaking of the transition from silent films to talking pictures, Singin' in the Rain highlights the evolution of Hollywood in the late 1920s. With Gene Kelly and Debbie Reynolds as the stars of the musical romantic comedy, they sing and dance their way through the movie.
Don Lockwood (Kelly) is known for his silent films with the beautiful (and tone-deaf) Lina Lamont (Jean Hagen). His displeasure with his costar and her vocals aren't much of an issue until the duo is forced to make their own talkie. Luckily, Kathy Selden (Reynolds) steps in as Lockwood's leading lady.
'The Apartment' (1960)
For Bud Baxter (Jack Lemmon), it is all work and no play in The Apartment. To move up the corporate ladder, the young insurance salesman offers up his place for his managers' extramarital activities. All is going well (besides judgment from his neighbors) until Baxter meets Fran (Shirley MacLaine).
While the couple's puppy love is simple and sweet, the connections they both have to the insurance executives make things more complicated. As Baxter questions whether his career is worth losing Fran, he discovers what truly makes him happy.
'Annie Hall' (1977)
Described as a nervous romance, Annie Hall (Diane Keaton) and Alvy Singer (Woody Allen) don't get their happily ever after...at least with each other. A unique take on the traditional romantic comedy, the audience looks back with Alvy on the rise and fall of a relationship that was special, complicated, and in the end, temporary.
Often times in the land of fictional fairytales, polar opposites attract. In the case of Annie and Alvy, the mellow and neurotic personalities are too mismatched. The ex-partners in Annie Hall take what they've learned as they move out and move on.
'When Harry Met Sally...' (1989)
If the genre had to be explained to aliens with one example When Harry Met Sally... would probably be used. The titular graduates both move from Chicago and land in New York. They continue to run into each other throughout the years. Both aren't sure their friendship can survive if they try to be more than that.
As Harry (Billy Crystal) and Sally (Meg Ryan) continue to date other people, they realize they may just be meant for each other. A New Year's Eve kiss seals the deal. The couple will be able to tell their future children all about what brought them together...although they may skip past the part about Sally's infamous public (but fake) "display of affection" at a bustling deli.
'Pretty Woman' (1990)
Richard Gere and Julia Roberts seem to be a match made in rom-com heaven. In Pretty Woman, Edward (Gere) and Vivian (Roberts) have a relationship that is strictly business. It's not long, however, before the outgoing and humorous Vivian melts Edward's cold and serious heart.
The song, the shopping spree, Vivian's laugh after Edward finally loosens up and pretends to snap her fingers in the jewelry case... it's all magical. As the genre continues to evolve, directors everywhere hope they can create a film that resonates with viewers decades later.
'Love Actually' (2003)
Ever get bored watching the journey of one couple finding love? Luckily, Love Actually keeps track of multiple romances. Taking place as the characters prepare for Christmas, some of the relationships are merrier than others.
As the best man secretly pines for the bride and work relationships become more personal, viewers keep up with dozens of intertwined lives. This emotional film is a great reminder that everyone has their own unique struggles, triumphs, and stories.
'Silver Linings Playbook' (2012)
The themes are less bright and shiny than in the typical rom-com, but Silver Linings Playbook absolutely has romance and comedy mixed in with the drama. With eight Academy Award nominations (Jennifer Lawrence won in the Best Actress category), the film resonates with those who view it.
After Pat Jr. (Bradley Cooper) is diagnosed with bipolar and forced to live with his parents, the former teacher is determined to look for the silver linings in situations. He meets Tiffany (Lawrence), a widow needing the support of a genuine and caring friend. Together they help each other get through the tough times and end up being responsible for each other's good moments, too.
'Look Both Ways' (2022)
Everyone knows and loves romantic comedies featuring characters switching places or using time travel to become their older selves. Look Both Ways takes a similar approach and has Natalie (Lili Reinhart) looking at two possible futures.
One reality involves a positive pregnancy test and raising a daughter while trying to achieve her professional goals. Another more career-focused future has Natalie meeting and falling in love with a colleague. In the end, it's comforting to acknowledge that there is often more than one path to reach the destination.