Top 10 Romantic Comedies of All Time

We all love a good romantic comedy. Witty, lighthearted humor, the promise and struggle of finding true love, and a happy ending tend to make up the plots of romcoms. For decades, people have laughed and cried alongside some of the most iconic characters in film history. We’ve got a list of 10 romantic comedies that are a must-see, from old black and white classics to recent films that made an impact.

10. Crazy Rich Asians

This 2018 film directed by Jon M. Chu is based on the novel by Kevin Kwan. It stars Constance Wu, Henry Golding, Gemma Chan, Lisa Lu, Awkwafina, Ken Jeong, and Michelle Yeoh. The story follows a Chinese-American professor who travels with her boyfriend to Singapore to attend his best friend’s wedding. Come to find out, her boyfriend’s family is one of the riches in Singapore. It’s full of drama, humor, tears, family dysfunction, and a whole lotta love. Crazy Rich Asians was also the first film by a major Hollywood studio to feature a cast who was majority of Asian descent since The Joy Luck Club in 1993. This film’s feel-good story, cute acting, and inclusiveness give it a spot on our list.

9. Crazy, Stupid, Love

Starring Steve Carell, Ryan Gosling, Julianne Moore, Emma Stone, Marisa Tomei, and Kevin Bacon, this 2011 film follows Cal Weaver and his wife Emily after finding out she cheated on him with a coworker. Cal moves out, leaving his two kids at home with his now ex-wife, and regularly goes to bars to ease the pain. He runs into Jacob Palmer, a womanizer who pities him and offers to help teach him how to pick up women. Crazy, Stupid, Love is a movie that both the ladies and the men can enjoy. There are subplots, backstories, and twists that all come together for a wonderful ending. Just trust us, no spoilers here.

8. Forgetting Sarah Marshall

This 2008 film was written by Jason Segel and starred himself, Kristen Bell, Mila Kunis, and Paul Rudd. Struggling musician Peter goes on a Hawaiian vacation to try and recover from his break-up with Sarah Marshall, his TV star ex-lover. All is well until Sarah and her new boyfriend show up at the same hotel. This one is full of laughs and awkward situations. Not to mention, Jason Segel and Kristen Bell are both hilarious and perfect for their characters. This is a must-see that will maintain “classic” status.

7. Pretty in Pink

Molly Ringwald plays an outcast girl who is torn between her childhood crush and the rich, popular guy at school. This 1986 film also stars Jon Cryer and Harry Dean Stanton. Molly Ringwald was (and still is) an icon as her character battles the struggles of dating out of her social sphere. This is a classic but satisfying 80s teen chick flick, but that doesn’t mean we haven’t watched it at least 8 times.

6. Sweet Home Alabama

Reese Witherspoon and Patrick Dempsey star in this 2002 film directed by Andy Tennant. Witherspoon plays a New York City socialite who has to return home to Alabama after getting engaged to finalize a divorce with her still-husband, Dempsey, after being separated for seven years. This film is packed full of iconic quotes that are still 100% relevant. Sweet Home Alabama takes you on an emotional rollercoaster of belly laughs and sobs. Witherspoon and Dempsey are funny, loveable, and unbelievably sassy. They take us on a journey of facing your past and learning who you are. Despite its witty lines, this film is a feel-good, charming, romantic rom-com.

5. Groundhog Day

This 1993 film starring Bill Murray, Andie MacDowell, and Chris Elliott tells the story of weatherman Phil Conners, news producer Rita Hanson, and cameraman Larry, who travel to Punxsutawney, Pennsylvania to cover, you guessed it, Groundhog Day celebrations. Phil had reassured viewers that an impending blizzard would miss the area but ended up stranded in Punxsutawney after the region gets blanketed in snow. When he wakes the next morning, he realizes the previous day’s events happening exactly as they had before. He’s stuck in a cycle repeated the same 24 hours over and over again with no way to escape it. He tries to explain this to Rita, his love interest in the film, by predicting exactly what would happen. Despite being a cynic, he uses these events to better himself and help the lives of others. This funny, heartwarming story has a picture-perfect romcom happy ended.

4. Four Weddings and a Funeral

Starring Hugh Grant, Andie MacDowell, James Fleet, Simon Callow, and more, this 1994 British film was directed by Mike Newell. Five friends, who are all single and wondering if they will ever find true love, one by one end up married. One friend, Charles, thinks he’s found the one in Carrie, the American. The film is full of feel-good moments, twists and turns, and very British humor. This classic is a true must-watch.

3. The Big Sick

This film premiered at the Sundance Film Festival in January of 2017 and became one of the highest-grossing independent films of the year after grossing $56 million worldwide (on a budget of only $5 million). The Big Sick was written by Kumail Nanjiani and Emily V. Gordon and is based on their real-life romance as an interethnic couple navigating cultural differences after Emily becomes sick. Kumail is an Uber driver and struggling stand up comedian in Chicago. His immigrant parents tried to set him up with Pakistani women, hoping for an arranged marriage, but he is not impressed. After a show, he meets Emily, a Caucasian student, and the two start dating secretly. After seeing the woman his parents are trying to set him up with, Emily breaks up with him. A few weeks later, Kumail finds out that Emily is in the hospital with a lung infection and is in a medically induced coma. The story goes on to follow the pair through ups and downs, and the journey of finding out what they truly believe.

2. The Princess Bride

Cary Elwes, Mandy Patinkin, and Robin Wright star in this 1987 film about a bedridden young boy and his grandfather, who reads him the “The Princess Bride,” a book that has been passed down through generations. The tale comes alive at the grandfather reads the story, a tale of romance and adventure as Buttercup, who is engaged to Prince Humperdinck, is kidnapped to start a war. Westly, her childhood love turned pirate, must save her. This film is full of adventure, fantasy, comedy, and of course, romance. Full of quotable lines (like “Hello. My name is Indigo Montoya. You killed my father. Prepare to die.”), this film is absolutely a classic that invites friends and families to sit down and enjoy it together.

1. When Harry Met Sally

This 1989 comedy written by Nora Ephron follows the lives of two friends, Harry and Sally, who have known each other for years and are afraid sex would ruin their friendship. They met when she gave him a ride to New York after they both graduated from the University of Chicago. They both search for love, but it never quite works out, but keep bumping into each other. A friendship blooms, and the question of whether or not men and women can be friends without sex getting in the way arises. Billy Crystal and Meg Ryan play the duo navigating their emotions. Carrie Fisher and Bruno Kirby make great supporting actors. Crystal and Ryan have fantastic on-screen chemistry and bring the lead characters to life. Viewers have called this one of the “wittiest and most funny romantic comedies.” Even though it came out in 1989, it is just as enjoyable today as it was back then. This romantic comedy stands the test of time and will be one that future generations will continue to watch and laugh along with.

There’s nothing better than a romantic comedy when you’re needing a pick me up, a laugh, or a night with friends. And these 10 certainly aren’t the only great choices out there. But they are all full of plot twists, relatable characters, sad moments, happy moments, and real-life problems that draw us in as an audience.



Add comment