romantic comedy movies ranked

29+ of the Greatest Romantic Comedies of All Time


| LAST UPDATE 11/12/2023

By Arianna Morgan

From adorable meet-cutes and overrated proms, romantic comedies will never go out of style. So, let's take a closer look at some of the best of all time, from Notting Hill to Love, Simon, and more.

30. My Best Friend’s Wedding (1997)

Strap in because Julia Roberts is one of the queens of rom-coms, so be prepared to see her name appear way more than just once on this list! But we'll start with an all-time classic, My Best Friend's Wedding.

My Best Friend’s Wedding (1997) TriStar Pictures via IMDb

Following the traditional love triangle scenario, Julianne Potter (Julia Roberts) and Michael O'Neal (Dermot Mulroney) made a deal that if they were single at 28, they would marry each other. But things get complicated when O'Neal says he's marrying Kimberly (Cameron Diaz), and Roberts realizes she's in love with her best friend!

29. The Big Sick (2017)

The Big Sick might not follow the classic romantic comedy guideline but offers viewers an inspiring story that, according to Vanity Fair, makes it one of the best romantic comedies of all time. Produced by Judd Apatow, audiences fall in love with Kumali Nanjiani and his wife Emily and their story.

The Big Sick (2017) FilmNation Entertainment via IMDb

Nanjiani, who plays himself in the film, meets Emily at one of his stand-up shows and quickly begins dating, but is worried about what his traditional Pakistani Muslim parents will think of their relationship. However, things quickly turn when Emily is left in a coma, and Kumali figures out how to bond with his girlfriend's American parents.

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28. How Stella Got Her Groove Back (1998)

Stella sure did get her groove back! In the iconic 90s film starring Angela Bassett and Taye Digs, audiences loved every moment of the two megastars' electric relationship, but in true rom-com form, there was definitely a catch preventing them from being together. In this case, it was two things: age and distance.

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Stella (Angela Bassett), a 40-year-old woman, traveled to Jamaica with her friend, Delilah, played by Whoopi Goldberg, when she ended up meeting a 20-something-year-old local island man, Taye Diggs, who swept her right off her feet. But when it was time to go home, they had some major decisions to make...

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27. Never Been Kissed (1999)

Starring one of our favorite rom-com queens, Drew Barrymore, Never Been Kissed is an all-time classic, and Vanity Fair agrees! Barrymore plays Josie Geller, a junior copywriter at the Chicago Sun-Times who goes undercover at her former high school to do some digging on teenage culture.

Never Been Kissed (1999) 20th Century Studios via IMDb

After making it with the popular kids, Barrymore experiences a lot of "firsts" as a 20-something-year-old writer back in high school-including falling in love with her English teacher, Sam Coulson (Michael Vartan), which gets tricky for obvious reasons. Fans love Josie so much that Barrymore often reprises her role on her talk show!

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26. How to Lose a Guy in 10 Days (2003)

Two decades ago, Kate Hudson and Matthew McConaughey starred in one the most re-watched movies of all time, How to Lose a Guy in 10 Days, and ever since then, we've been wondering more and more about those "How To" columns, and more importantly how do we get involved?!

How to Lose a Guy in 10 Days (2003) Paramount Pictures via IMDb

Advice columnist Andie Anderson (Kate Hudson) looks for a centerpiece for her article on how to get a man to leave you in 10 days when she finds Ben Berry (Matthew McConaughey), an exec who is overly confident in his suave game. But in true rom-com form, things get complicated when their plans don't go according to plan!

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25. 27 Dresses (2008)

We all know that one girl who served as a bridesmaid one too many times, so this is for you, girl. According to the writer, Aline Brosh McKenna, the 2008 romantic comedy is actually based on a friend of McKenna's who has been a bridesmaid too many times and now officiates weddings!

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So what makes 27 Dresses one of the best of all time, according to Good Housekeeping? This feel-good rom-com sees Jane (Katherine Heigl) serve as a bridesmaid yet again for her sister, Tess, but this time marrying a man she secretly loves. But audiences are rooting for her fairytale ending once she meets Kevin (James Marsden).

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24. The Wedding Singer (1998)

The best part of any rom-com is that they are entirely relatable. Everyone has been through heartbreak, and everyone is looking for love; it might be that simple! The Wedding Singer gives audiences both heartbreak and hopeful romance, making it one of our favorite '90s movies of all time.

The Wedding Singer (1998) New Line Cinema via IMDb

After being left at the alter, Robbie (Adam Sandler) is stuck and brokenhearted, with one of the most romantic jobs out there: a wedding singer. But things take a turn when he meets Julia (Drew Barrymore), who hired him as her wedding singer. Robbie quickly finds himself falling in love with her and is determined to win her over.

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23. 13 Going on 30 (2004)

At 13, we all wanted to be 30, and now that we're 30 we all wish we were 13. Ironic, huh? Well, thanks to one of the greatest rom-coms of all time, we can always time travel back to 13 while we indulge in our 30s. Jennifer Garner steals the limelight in this one as Jenna Rink, a 13 year old girl who gets her wish of being an adult.

13 Going on 30 (2004) Columbia Pictures via IMDb

After her fantasy of being a working adult comes to life, Jenna soon figures out that adulthood isn't quite as she imagined it. Lucky for her she reconnects with her old pal Matty (Mark Ruffalo) who helps her navigate her 30s, as she quickly realizes her feels for Matty go much farther than just friends.

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22. Pretty Woman (1990)

We told you Julia Roberts would be featured on this list multiple times! In this 1990, one of the best rom-coms of all time was born, and Good Housekeeping agrees! It might sound cliche, but Pretty Woman is a true example that love can't buy happiness, no matter how hard you try.

Pretty Woman (1990) Silver Screen Partners via IMDb

When a successful businessman Edward (Richard Gere), finds Vivian (Julia Roberts) on a trip to L.A., the two figure out they have a lot more in common than they could have thought after spending a weekend together. The couple fall madly in love but are faced with the challenges of connecting their two different worlds together.

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21. The Apartment (1960)

Although this film is from the '60s, it feels as relevant as ever. The Apartment might not be your traditional romantic comedy, but it explores the dark side of falling in love and the hardships of being in love with the wrong person at the wrong time, as well as introduces the concept behind the "nice guy" character. Classic.

The Apartment (1960) The Mirisch Company via IMDb

C.C Baxter (Jack Lemmon) finds himself in a moral entanglement when he lends his apartment to his bosses for their affairs in exchange for being promoted. When Baxter finds out that his boss's mistress is Fran Kubelik (Shirley MacLaine), with whom he is in love, he must decide if going after her is worth sacrificing his career.

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20. Four Weddings and a Funeral (1994)

Believe it or not, this brilliant 90s film actually launched Hugh Grant's career as the leading man in romantic comedies for years to come! According to Grant, he was about to give up on acting before coming across this script, and well, we're thankful that didn't happen!

The Apartment (1960) Film4 Productions via IMDb

From the title alone, we're intrigued. With Four Weddings and a Funeral, we saw love celebrated and the sadness of death all tied up into 120 minutes. Charles (Hugh Grant) and Carrie (Andie MacDowell) continue to cross paths in too many places, making Charles believe they could be each other's soulmates.

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19. Sixteen Candles (1984)

Let's call this one a classic. Sixteen Candles skyrocketed Molly Ringwald's career as an actor and John Hughes's career as a director. Molly Ringwald's character Samantha was the perfect example of teenage angst, making it extremely relatable to the millions of people who quickly loved her character.

Sixteen Candles (1984) Universal Pictures via IMDb

Samantha's 16th birthday was around the corner but was forgotten due to her sister's wedding. Meanwhile, she had a big crush on older boy Jake (Michael Schoeffling) but thought her chastity status wouldn't roll over well with the hot seniors. But it turns out nerdy Ted (Anthony Michael Hall) actually cared about her the most!

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18. Kissing Jessica Stein (2001)

Although this one doesn't have the happy ending like most rom-coms do, Kissing Jessica Stein explores the untapped realm of on-screen LGBTQ+ relationships that is often missed in modern media, and for that, it holds a pivotal role in the film. Not to mention, it holds all the classic clichés we love in a rom-com.

Kissing Jessica Stein (2001) Searchlight Pictures via IMDb

Jessica (Jennifer Westfeldt), a NYC journalist with an overbearing Jewish mother, was tired of looking for The One. She then came across an appealing ad in the "women seeking women" section and ended up meeting Helen Cooper (Heather Juergensen), and they clicked. But then they were faced with all life's dating hurdles.

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17. Moonstruck (1987)

Some may say that Moonstruck is Cher's best acting role to date, and well, we couldn't agree more. Moonstruck tells the story of a young Italian-American widow, Loretta Castorini (Cher), living at home with her parents in Brooklyn, who agrees to marry Johnny Cammareri (Danny Aiello) in the opening scene of the film.

Moonstruck (1987) Metro-Goldwyn-Mayer via IMDb

However, she quickly realizes that she's way more into her fiancé’s younger brother, Ronny (Nicolas Cage) than she is into her future husband. She tries to resist, but Ronny is pulling out all the stops when it comes to impressing Loretta, and soon, the Italian heroine finds herself falling madly in love with the wrong person.

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16. Say Anything…(1989)

There are a few movie scenes that will forever stick with us, one of which is when Llyod stands under Diane's window holding a boombox playing In Your EyesSay Anything... solidified the romance behind the boombox in rom-coms for years to come, so thank you.

Say Anything (1989) 20th Century Studios via IMDb

Starring the beloved John Cusack as Lloyd, a young hopeless romantic who is determined to catch the attention of the gorgeous and brilliant Diane (Ione Skye), Say Anything is a true first love story. When Diane surprisingly expresses interest in Llyod, her father is first to disapprove.

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15. The Princess Bride (1987)

Years after its release, The Princess Bride developed a cult following, as it developed into one of the most beloved and quoted movies of all time. Based on the William Goldman novel, the loving tale tells the story about Buttercup, a young girl living in the kingdom of Florin, and her story of finding her one true love!

The Princess Bride (1987) Buttercup Films Ltd. via IMDb

Buttercup (Robin Wright) meets Westley (Cary Elwes), a farmhand whose famous words, "as you wish," become the stand-out of the film and the two fall in love. After being separated, the two must fight the evils of the kingdom to make sure they end up together.

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14. Roman Holiday (1953)

Audrey Hepburn, what else is there to say? She did win an Oscar for her role as Princess Ann, after all. The classic film from the 50s uses the traditional romantic comedy formula we know and love today: girl meets boy, they fall in love, and things get shaky.

Roman Holiday (1953) Paramount Pictures via IMDb

Princess Ann goes off on a wild adventure in Rome when she falls asleep on a park bench and wakes up to a handsome American reporter, Joe Bradley (Gregory Peck), who saves the day. The couple's connection is instantly electric, but of course, real-life challenges start to settle in, threatening their relationship, and then what?

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13. 10 Things I Hate About You (1999)

Right after 10 Things I Hate About You was released, it was recognized for all its rom-com brilliance. Starring Julia Stiles as Kat Stratford, the smart, beautiful, independent teen who is not interested in dating until house rules say that her younger sister Bianca (Larisa Oleynik) can't date until Kat does.

AJ Pics / Alamy Stock Photo

Shortly after, Kat meets Patrick Verona (Heath Ledger) and starts to warm up to being vulnerable around someone else. Besides the typical house party and prom night storylines, 10 Things I Hate About You taught us some pretty valuable lessons for years to come. Heath Ledger was incredible and let people see and believe in you.

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12. To All the Boys I’ve Loved Before (2018)

According to Rotten Tomatoes, this film scored 96% with critics writing, "To All the Boys I've Loved Before, plays by the teen rom-com rules, but relatable characters and a thoroughly charming cast more than make up for the lack of surprises." And we couldn't agree more!

Lifestyle pictures / Alamy Stock Photo

The reclusive high school junior Lara Jean Covey (Lana Condor) writes passionate love letters to five boys she secretly has crushes on. Her worst nightmare later comes true, and the boys get ahold of the letters, leaving her in a state of panic. To All the Boys I've Loved Before later became one of three films.

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11. Sleepless in Seattle (1993)

What's a romantic comedy without Nora Ephron? Ephron is responsible for writing and directing one of the world's most beloved romantic comedies of all time, Sleepless in Seattle. Thirty years later, Meg Ryan and Tom Hanks meeting on top of the Empire State Building will be forever engrained in our memory.

RGR Collection / Alamy Stock Photo

Following the death of his wife, Sam Baldwin (Tom Hanks), and his son, Jonah (Ross Mallinger), move to Seattle. Jonah (Ross Mallinger) somehow gets his father to make a vulnerable appearance on a radio show, hoping to find a new woman for his dad. Annie (Meg Ryan) hears the conversation and begins to search for this perfect man.

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10. Notting Hill (1999)

When Julia Roberts and Hugh Grant take center stage, there is very little that can go wrong; in fact, so much goes right that almost 25 years later, Notting Hill is that rom-com that is guaranteed to feel good. The storyline is simple; it's written like a modern fairy tale, but it's Grant and Roberts' connection that is undeniably lovable.

Notting Hill (1999) Caravan Pictures via IMDb

We have a British bookstore owner, William, who falls head over heels for an American actress, Anna, and their perfect meet-cute love story that keeps audiences coming back year after year for more. And in the wise words of Roberts, "I'm just a girl, standing in front of a boy, asking him to love her," we leave you here.

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9. Love & Basketball (2000)

Monica and Quincy were so perfect for each other it was almost hard to believe that the actors weren't actually together in real life. Growing up, Monica and Quincy shared the dream of becoming professional basketball players, and after years of friendship, the two begin to fall for each other, but their careers step in the way.

Cinematic / Alamy Stock Photo

According to director Gina Prince-Bythewood, Love & Basketball "set the tone" for her career later on. Vanity Fair reported, "I think it is so important for your first film to do that, to reflect who you are, say who you are, introduce yourself," adding, "Which is why I'm so glad it was Love & Basketball and not something I had almost done."

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8. Groundhog Day (1993)

Groundhog Day explores the continuous life theme of death and rebirth, all while being a rom-com classic. Bill Murray stars as Phill, a weatherman who covers the senseless ritual in which a groundhog looks for its shadow to determine if there will be six more weeks of winter or if there will be an early spring.

Groundhog Day (1993) Columbia Pictures IMDb

Phil ends up in a continuous 24-hour time loop, consistently reliving the same 24 hours over and over again, meaning he gets rejected by his producer, Rita (Andie MacDowell), again and again. The movie covers Phil's sense of curiosity and the importance of time while intertwining an addicting love story.

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7. His Girl Friday (1940)

According to Rotten Tomatoes, His Girl Friday is "possibly the definitive screwball romantic comedy," making it one of the best romcoms of all time. Released in 1940, the film explores the nuanced relationships from that time period, including the quick and witty banter!

His Girl Friday (1940) Columbia Pictures IMDb

Newspaper editor Walter Burns (Cary Grant) finds out that his ex-wife, a strong news reporter named Hildy (Rosalind Russel), is getting re-married, and he's determined to do what he can to sway her decision. When Burn offers his wife an irresistible breaking story, things get complicated.

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6. The Philadelphia Story (1940)

After earning 100% on Rotten Tomatoes, The Philadelphia Story was called "an unqualified classic" for its "wonderfully witty script," "spotless direction," and "excellent lead performances" by critics. Based on the 1939 Broadway play of the same name, this romantic comedy landed its spot as one of the best of all times.

The Philadelphia Story (1940) Metro-Goldwyn-Mayer IMDb

It features Katharine Hepburn as Tracy Lord, a socialite who has recently split with her husband, C.K. Dexter Haven (Cary Grant), due to his drinking problems (amongst other things). Tracy is lined up to get re-married but has second thoughts when she bumps into her ex-husband and meets reporter Macaulay Connor (James Stewart).

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5. Clueless (1995)

Almost thirty years later, Clueless remains a cult classic. Cher, played by Alicia Silverstone, is a wealthy popular high school student, and we must praise her unbelievable wit and charm. Her one-liners, from "You try driving in platforms" to "Oh, I'm having a Twin Peaks experience" will forever go down in history.

Maximum Film / Alamy Stock Photo

Cher's passion for success drives her to give Tai (Brittany Murphy) a makeover, but when she becomes more popular than her, she turns to her step-brother (Paul Rudd) for guidance and ends up falling head over heels for him. Clueless hit a major cultural milestone back in the 90s that still holds major influence and love today.

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4. Love, Simon (2018)

"I deserve a great love story," Simon Spier, played by Nick Robinson, says in the film Love, Simon. The teenage rom-com stars Robinson, a high-school student with a loving family, great friends, and a thriving social calendar, who spends much of his time worrying about what would happen if he came out as gay.

Love, Simon (2018) 20th Century Studios via IMDb

Audiences follow along as Simon starts forming a romantic relationship with an anonymous classmate online who recently came out. Love, Simon allows audiences to see a different kind of main character, one that isn't often portrayed in movies, while embracing his lovable identity and being.

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3. Bridget Jones Diary (2001)

We can all relate to Bridget Jones; that's what makes this one so great. Renée Zellweger's portrayal of the hopeful heroine Bridget Jones is forever embedded in our memory; specifically her sitting at home indulging in wine and cake, singing All by Myself in her living room.

Pictorial Press Ltd / Alamy Stock Photo

When Bridget Jones decides it's time for a life change, she also decides it's time to invest in a diary. Audiences fall in love with Bridget's spectacular storytelling and sudden feast for life, including her hilarious experiences with Mark Darcy (Colin Firth) and Daniel Cleaver (Hugh Grant).

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2. You’ve Got Mail (1998)

Let's talk about rom-com queens real quick. There's just no way the genre could even exist without the wonderful actress Meg Ryan or brilliant multi-hyphenate Nora Ephron. Together, they've made some of the world's most successful romantic comedies, including a forever favorite, You've Got Mail.

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Kathleen (Ryan) and Joe (Tom Hanks) develop an anonymous online romantic relationship despite their hate for one another IRL. They don't know the truth about who is behind the screen, but after finding out, they are tasked with navigating their conflicting feelings for one another.

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1. When Harry Met Sally (1989)

And now for the greatest rom-com of all time, When Harry Met Sally. Written by Nora Ephron and directed by Rob Reiner, the duo takes all the right ingredients of a perfectly constructed rom-com and puts it together to produce the most beloved romantic comedy of all time.

Maximum Film / Alamy Stock Photo

Audiences fall in love with the relatable dynamic between Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan). As college graduates, Harry and Sally argue over the commonly asked question, "Can men and women just be friends?" To no one's surprise, they can't, and to everyone's approval, they become more than just friends.

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