25. Groundhog Day (1993)
Image Source: Nerdist
Bill Murray in a romantic comedy? Yes, please. Regardless of what day it is, Groundhog Day is an ideal romantic comedy to watch. The film transcended an easily forgettable holiday and found something incredibly romantic in being caught in-between seasons. Murray plays Phil Connors, a self-loathing TV reporter trapped in a time loop to last more than 40 years. This gives him enough time to successfully court Rita (Andie MacDowell). It is charming, and all-around worth repeating again…and again…and again.
24. Coming to America (1988)
Image Source: Mentalfloss
What do I love about this unlikely pick? On one hand, it was a romantic comedy. On the other hand, it was a film about black culture. This film was way ahead of its time. 30 years later, it still remains one of the very few mainstream Hollywood black romantic comedies. The innocence and humor Eddie Murphy brings to the role of Prince Akeem makes this film great. There’s also great interplay between nosy New York barbers adding their two cents to every conversation, Murphy’s and Arsenio Hall’s array of characters, and everything about James Earl Jones as a king. In the end, Lisa (played by Shari Headley) falls in love and get both the man and the prince.
23. You’ve Got Mail (1998)
Image Source: Austin Chronicle
You’ve Got Mail is the last of Nora Ephron’s genre-defining romantic comedies. Its the second film made with Meg Ryan and Tom Hanks, who circle each other as sparring partners Kathleen Kelly and Joe Fox. Kathleen is the owner of a small children’s bookstore (which he inherited from her deceased mother). It becomes at risk of closure thanks to the opening of Joe’s megastore. They meet in a chat room, and subsequently fall in love not knowing who the person on the other side of the screen truly is. Despite its outdated tech talk, it’s a beautiful movie — and thus a real classic rom-com.
22. How to Lose a Guy in 10 Days (2003)
Image Source: Bustle
Alright, Alright, Alright. Only a true rom-com would have leads named Andie Anderson and Benjamin Barry. It’s a film that centers on a cool girl, whose chemistry with a chauvinistic man’s man is undeniable. Andie (Kate Hudson) works for a women’s magazine that is “growing”; Benjamin (Matthew McConaughey) is wearing shirts, and “Knicks” tickets were of great value. Andie wants to write about subjects with substance — which, for the moment, requires her to ensnare a man and torture him to the point of breaking up. He, meanwhile, is simply trying to win a big campaign at work by proving he can make any woman fall in love with him. They fall in love, and its basically impossible to do anything but cheer them on in the process.
21. Moonstruck (1987)
Image Source: Mentalfloss
Moonstruck follows Loretta Castorini (a radiant Cher) — a widow from Brooklyn who finds herself in a tough spot when she falls for her fiancé’s estranged younger brother (Nicolas Cage). In the process, a romantic comedy is born. The film is, at its core, a big corny movie about people coming to terms with themselves and the people they love. It’s packed with speeches on love — including Cage’s declaration to Cher that prompts that famous “snap out of it!” series of slaps. Despite all the noise and emotion, Moonstruck is very subtle and gentle. It loves its characters and refuses to limit their personalities to a few comic traits. It is true romance at its finest.
20. Sabrina (1954)
Image Source: Pixels
Sabrina Fairchild (Audrey Hepburn) has been crazy over playboy David Larabee (William Holden) her entire life. Sadly, he never gives her a second glance. That is, until Sabrina returns from Paris two years later a more culturally refined lady. She then gains the instant attention of David. However, with the difference in their classes, the family refuses to give their blessings and enlists David’s brother Linus (Humphrey Bogart) to break them up. Linus will do whatever it takes…until he starts forming feelings himself for the beautiful Sabrina.
19. The Holiday (2006)
Image Source: Buzzfeed
In London, Iris Simpkins (Kate Winslet) writes a wedding column in a newspaper. She simultaneously fosters an unrequited and unhealthy love for her colleague Jasper. Near Christmas, she is informed that he is in fact newly engaged (thus turning her life upside down). In Los Angeles, Amanda (Cameron Diaz) has just split her boyfriend after finding out he has cheated on her. Both needing to escape, they impulsively agree to swap houses for the holidays. While in Surrey, Amanda meets the very attractive brother of Iris (umm..hi Jude Law). Iris meets film composer Miles (Jack Black). This film is definitely a must-see for this holiday season!
18. Amelie (2001)
Image Source: WUWM
This is not a movie that many would traditionally put into the romantic comedy genre. This lovely film, directed by Jean-Pierre Jeunet, is about a painfully shy Parisian waitress who finds peace and joy in the little things of life. Audrey Tautou is brilliant — and brings every ounce of heart to this role. Romance is never Amelie’s goal. However, this all changes upon being hit in the face by her future love (Nino) at a train station. Amelie is without a doubt a delicious pastry of a movie.
17. Pretty Woman (1990)
Image Source: TIME
There should never be a rom-com list that doesn’t include this movie. What is there to say about the 1990 tale of the charming, gorgeous prostitute (played by a young Julia Roberts) and the Wall Street corporate shark (Richard Gere) who meet and fall in love? Pretty Woman remains one of the most popular movies — as well as one of the highest grossing romantic comedies of all time. Directed by Garry Marshall, Pretty Woman was quite controversial upon hitting the theaters. In the post-#Metoo context, this revolutionary rom-com is a legitimate work of cinema with serious concerns about men, women, sex, class and power.
16. Something’s Gotta Give (2003)
Image Source: TODAY
In my opinion, Something’s Gotta Give is Nancy Meyer’s best romantic comedy to date. This is lovely film about the romance between Jack Nicholson and Diane Keaton. At the time, many industry insiders and studios were wary of making a film about people in their 60’s finding love. However as it turned out, audiences were ready for a mature romance. This is a romance that involves a hilarious scene where Keaton takes Nicholson’s blood pressure before having sex. “I think its irresponsible not to,” she tells him. The film would gross over $200 million dollars worldwide and earn Keaton an Oscar nomination.
15. Bringing Up Baby (1938)
Image Source: Chicago Reader
Oh how I love Katharine Hepburn. Considered the greatest actress to have ever lived, here we see her playing the eccentric Susan Vance. Written by Dudley Nichols and Hagar Wilde, Bringing up Baby opens on Cary Grant’s absentminded paleontologist David Huxley. David is waiting the arrival of a rare bone he needs to complete a brontosaurus skeleton he’s been working on for four years. He’s about to be married, while simultaneously preparing to meet the lawyer of Mrs. Elizabeth Random — a wealthy woman who’s considering making a million-dollar donation to his museum. As he attempts to impress the lawyer, he continually gets undermined by the beautiful Susan Vance (who coincidentally turns out to be the niece to Mrs. Random). Although David tries to return to a life of normalcy, he keeps finding himself sucked into the vortex of chaos that surrounds Susan. It’s a touching film, and definitely a rom-com must see.
14. Bridesmaids (2011)
Image Source: Moviefone
Though it’s a genre constantly being written off as cinema rubbish, rom-coms continue to thrive and evolve. Bridesmaids is an example of that. I mean, who ever thought getting food poisoning in a wedding dress could so hilarious? Bridesmaids is about the love between friends. What ultimately drives this amazing film is the desire Annie (Kristin Wiig) has to reconnect with her best friend Lillian (Maya Rudolph). With heartfelt moments and non-stop laughs, we get a powerhouse performance from Wiig (even as Melissa McCarthy steals the show in a complementary role).
13. It Happened One Night (1934)
Image Source: Variety
It Happened One Night captures lust and love without a whole lot. It involves an instantly iconic shirtless Clark Gable, and a road trip plot repeated endlessly in the decades since but never quite matched. This is screwball comedy, when women behaved wildly and and dialogue came quickly. The film stars Gable and Claudette Colbert, who plays the heiress on the run being hunted down by Gable. Their chemistry is hilarious and lovable, both perfectly matched in wits (until it turns irrepressibly romantic). The film went on to win all five major Academy Awards.
12. Four Weddings and a Funeral (1994)
Image Source: Deadline
When I think of the greatest rom-coms of all time, it would be impossible not imagine Hugh Grant’s charming, precocious smile. A great British classic, Four Weddings and a Funeral is a delightful and sly comedy about people who seem to live out their lives publicly attending weddings. We never know what they truly do for a living, nor do we care. The film follows Charles (Grant) who becomes smitten with an American woman named Carrie (Andie Macdowell). Charles keeps running into Carrie at weddings (and a funeral). The ensemble cast is charmingly quirky, but the film is best known for launching Grant and his long career as the floppy-haired, awkwardly romantic hero.
11. Roman Holiday (1953)
Image Source: Variety
There’s a wonderful moment in Roman Holiday when Princess Ann (played by Audrey Hepburn) rebels against the goodwill tour she is making of Europe after arriving in Rome. She soon meets Joe (Gregory Peck), a reporter who agrees to show her the city. Their adventures are amusing and natural. Naturally, the two fall in love during this Roman holiday. The chemistry between the two actors is breathtaking. No matter how the story ends, we cant help but root for them.
10. Beauty and the Beast (1991)
Image Source: Variety
It truly is a tale as old as time. Lonely powerful men have been making off with damsels and then hiding them away since Greek mythology and before. However, Disney scored with this animated musical by reanimating that classic story in a way that’s appealing to our eyes, ears, and hearts. Making the stakes between the characters high and real — even when accompanied by a singing Angela Lansbury teapot — we couldn’t help but fall in love with Beast, alongside Belle.
9. Love Actually (2003)
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Love Actually is basically a belly-flop into the sea of romantic comedy. It contains about a dozen couples all in love; some of them fall out of love whilst other double up or change partners. The film is written and directed by Richard Curtis, the same man who brought us Four Wedding and a Funeral, Notting Hill, and Bridget Jones Diary. The movies only flaw is also a virtue: It’s jammed with stories, characters, warmth, until at times Curtis seems to be working from a checklist of obligatory love situations and refuses to leave anything out. At 129 minutes, Love, Actually is entirely too long. But please I beg you, don’t let that stop you from watching.
8. My Best Friend’s Wedding (1997)
Image Source: News AV Club
When Julianne (Julia Roberts) dumped Michael (Dermot Mulroney) as a boyfriend in college, she made him her new best friend. They made a pact: if they were still single at 28, they would marry each other. Now, they’re both 28 and Michael has called Julianne to say he’s in Chicago and wants to meet up. She’s touched, as she’s always really loved the guy. But Michael isn’t calling to propose. He’s calling to explain he’s engaged to be married in three days — to a junior at the University of Chicago (Cameron Diaz). This is not good news for Julianne. My Best Friend’s Wedding tells the hilarious story of how she tries to sabotage the wedding and win the man she should have married all along. With the luminous Julia Roberts as lead, we all know how the movie with end right? Well, not necessarily.
7. While You Were Sleeping (1995)
Image Source: Biography
I must have seen While You Were Sleeping over a hundred times. My all-time favorite Sandra Bullock film, While You Were Sleeping is one of those movies that blind sides you with its charm. The movie shows Bullock playing a toll woman named Lucy. She has an endearing crush on Peter (Peter Gallagher), a commuter who she looks to as the perfect man. One day, Peter is mugged and thrown onto the train tracks. Lucy rushes out of her booth and saves his life. Peter is rushed to the hospital, where he is in a Movie Coma (a medical condition that requires him to remain unconscious as long as is convenient for the plot). Through a silly understanding, the members of Peter’s family become convinced Lucy is his fiancee. Enter Peter’s dreamy brother, Jack (Bill Pullman) and you have yourself a rom-com. Its love story in which sweetness is more important that passion.
6. Bridget Jones’s Diary (2001)
Image Source: Moviefone
Bridget Jones’s Diary is a beloved film about a heroine both lovable and human that understands the charm of preserving originality. For anyone who’s ever found herself sitting at home with dangerous quantities of wine and cake (whilst belting out “All by Myself” alone), this one was bound to be a rom-com home run. Renee Zellweger’s hapless, relatable Bridget Jones and her competing love interests — played with distinctly British charm by Colin Firth and Hugh Grant — became an instant hit in 2001. It’s hard to think of a more satisfyingly absurd climax than the moment Bridget chases Mr. Darcy down a snowy London street in nothing but a pair of zebra undies and sneakers.
5. Notting Hill (1999)
Image Source: Town&Country
The moment we see Hugh Grant and Julia Roberts on screen together, we want to see them embracing. With that said, a romantic comedy like Notting Hill is about delaying the inevitable. After all these characters are from two different worlds. Roberts plays Anna Scott, one of the most famous movie stars in the world. Grant’s character, William, runs a modest little travel bookstore in London. The film is bright and full of wit and intelligence, especially when it comes to the ensemble of characters surrounding William. We know they’re destined for each other, but we are always quicker to see things then the characters themselves. After all, she’s just a girl standing in front of a boy, asking him to love her. With Notting Hill, Richard Curtis hits all the requisite notes just right.
4. The Philadelphia Story (1940)
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The Philadelphia Story is one of those legendary Hollywood films — and not just because it stars Cary Grant, James Stewart, and Katharine Hepburn. Hepburn plays Tracy Lord, the eligible daughter of a well-off Philadelphia family due to marry. When Grant and Stewart’s characters fall for Tracy, chaos ensues. Possessing excellent casting, a great storyline, and a sharp script, The Philadelphia Story remains a classic of the genre, and one of Hepburn’s best role to date.
3. My Big Fat Greek Wedding (2002)
Image Source: VOX
My Big Fat Greek Wedding is narrated by Toula Portokalos (Nia Vardalos). Like all Greek women, she says, was put on this earth for only three purposes: to marry a Greek man, have Greek babies, and to feed everyone until the day she dies. Toula eventually meets her love, Ian (John Corbett). The couple soon gets engaged to be married. Vardalos’ ode to Greek culture in all its beauty and frustration focuses on the quest of her character to get her family to accept her non-Greek partner. Her family is full of kooky characters and their absurdist take on life spills out of every scene. The movie is warm-hearted in the way a movie can be when it knows its people inside and out. No surprise, this remains, the highest grossing romantic comedy of all time.
2. Sleepless in Seattle (1993)
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Nora Ephron’s Sleepless in Seattle begins with Sam (Tom Hanks) mourning the loss of his beloved wife. Sam and his eight-year-old son Jonah move to Seattle, where Jonah calls a radio talk show about his depressed dad and persuades him into talking about his feelings on air. The story of Sleepless in Seattle makes every single woman in America want to hug him. Baltimore journalist Annie (Meg Ryan) falls in love with Sam upon hearing him speak. Her journalist tenacity allows her to track down Mr. Sleepless in Seattle even in a pre-Google, pre-Facebook environment. Hanks is perfect as the bereaved husband and doting father, and Ryan is incredibly charming — even when she verges on stalker territory with her willingness to fly across country in search of her true love. By the end of the film, you cant help but cheer for the duo’s long waited meet atop the Empire State Building.
1. When Harry Met Sally (1989)
Image Source: Tribeca
If this was a top 10 list, this film would still be on it. Same with top 5 for that matter. It’s in the running for the best rom-com of all time because it’s snappy, sultry, and sassy. It’s cinematic perfection — thanks to the great Nora Ephron with direction by Rob Reiner. When Harry Met Sally established Meg Ryan as America’s sweetheart. It became the gold standard Hollywood has tried to emulate ever since. Only Ephron and Reiner could achieve the alchemy by combining the sweetness of Ryan’s Sally Albright with the cranky pessimism of Billy Crystal’s Harry Burns. Re-watching the film today, is a bleak reminder that Ephron’s endless talent, wit, and intelligence is no longer with us. But thankfully, this film will live on forever.