Best Romantic Comedies - Featured Image

Tired of scrolling through Netflix? Feeling lonely? Searching for ‘the one’? No matter what prompted you to Google “best romantic comedies,” by the time you leave, two things are certain: you’ll be inspired to make your own list of favorites and you’ll open up that ice cream tub and turn on the TV. So, without further ado, here are the best romantic comedies of all time.

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Best Romantic Comedies

A quick note on criteria

When we set out to rank the best Romantic Comedies of all time, we had to set some ground rules. As with any list of Romantic Comedies, subjectivity plays a huge part. To even the playing field, we came up with four categories to make our selections.

"Waterworks" ranks how emotionally stirring these Romantic Comedy movies get; "Comedy" obviously assesses the laugh factor; "Originality" measures how the film brings a unique perspective to a well-worn formula; and "Impact" relates to how iconic and influential the film has been amongst the great Romantic Comedies.

Classic Rom Coms

25. Bringing Up Baby (1938)

Bringing Up Baby  •  Torn Dress

Sometimes, you gotta pay homage to the classics, and when talking rom coms, that means Cary Grant (His Girl Friday, Charade, The Philadelphia Story) and Katherine Hepburn (The Philadelphia Story, Woman of the Year, The African Queen) in Howard Hawks' Bringing Up Baby.

Grant and Hepburn bounce off each other with tremendous chemistry in this screwball comedy about a paleontologist and a young heiress. The premise and resulting drama is all a bit absurd (hence the 'screwball' in screwball comedy) but provides good fun and ample romance.

50%
Waterworks
80%
comedy
100%
originality
100%
impact
82%
OVERALL SCORE
  • Classic
  • Multi-Dimensional
  • Female-Driven
  • Cartoony
  • Old Fashioned
  • Predictable

Classic Rom Coms - bringing up baby

Conclusion

A classic screwball with high-concept thrills, a couple leopards, Cary Grant, and a Hepburn. What more can one ask for?  

Classic Rom Coms

24. His Girl Friday (1940)

His Girl Friday  •  Love Triangle

Cary Grant strikes again in another Howard Hawks masterpiece. This time, he's paired with Rosalind Russell in this newsroom comedy, romance, journalism flick.

A clear precedent to films like Broadcast News, His Girl Friday takes full advantage of the workplace setting as well as the “you’re marrying the wrong man” debate. It gets a little crazy towards the end, as a lot of these older Rom Coms tended to do.

A primarily female-driven story, there’s some strange housewife talk that doesn’t exactly mirror current feminists views. Still, nothing goes too far, especially considering the 1940 release date. 

50%
WATERWORKS
80%
comedy
100%
originality
100%
impact
82%
OVERALL SCORE
  • Classic
  • Multi-Dimensional
  • Female Driven
  • Cartoony
  • Old Fashioned
  • Predictable

Classic Rom Coms - His Girl Friday

Conclusion

At 92 minutes, His Girl Friday is full of laughs, romance, Cary Grant, and a surprisingly tight story for such a 1940s film.  

Something About Mary Clip  •  Frank and Beans

The romantic comedy that starts our list earned $369 million at the box office, making it the list’s top earner. One after another men try to woo darling Mary (played by Cameron Diaz) resulting in embarrassment, devastation, and some extravagant planning.

Ben Stiller, still a relative unknown at the time, holds his weight, en route to being one of the main comedy stars of the next 10 years. It’s a pure comedy, so the dramatic beats and heavy moments are lacking, but Stiller is easy to root for, it’s a fun watch, and earns its spot.

40%
WATERWORKS
95%
comedy
75%
originality
85%
impact
83%
OVERALL SCORE
  • Memorable Moments
  • Farve
  • Backstabbing
  • Kinda Slapstick
  • Not PC
  • Over the Top

Best Rom Coms - There’s Something About Mary

Conclusion

While not as deep or emotional as some of the films to come, There’s Something About Mary is funny first and romantic second. It knows what it is.

Sad Romantic Comedies

22. Lost In Translation (2003)

Lost In Translation  •  Suntory Time!

Now, it’s unclear if the relationship in this rom com is truly romantic… but there is a kiss at the end and some definite undertones. It doesn’t help that Scarlett Johansson was 18 at the film's release while Bill Murray (always in good romantic comedies) just turned 53, but that’s neither here nor there.

The two bond over depression and pointlessness for a week in Tokyo. As opposed to the rosy, glorious display of travel, Lost In Translation flips the cliche, showing how distancing it can be. The comedy (which was largely improvised) comes from pretentious LA travelers, obsession with movie stars, and poor Japanese translation.

Combine all that with some great Bill Murray, and you get a Best Original Screenplay Oscar.

85%
WATERWORKS
70%
comedy
95%
originality
90%
impact
84%
OVERALL SCORE
  • Life Crisis
  • Surprising Chemistry
  • Suntory Commercial
  • Slow
  • Age Difference
  • Not For Everyone

Sad Romantic Comedy Movies - Lost in Translation

Conclusion

It’s not the cute, fun romantic comedy to watch with your significant other, it achieves something deeper. It’s more of a drama than traditional rom com.

Funny Romantic Comedies

21. Anchorman: The Legend of Ron Burgundy (2004)

Anchorman  •  Sex Panther 

Maybe one of the most well-known comedies ever, technically Anchorman is also a workplace romance. And while I count a lot more gut-punching laughs then heartbreaking romantic moments, Ron does jump into a bear-pit to save Veronica at the end.

Anchorman  •  Bear Fight

In the original script, the story still focused on newsmen but involved a plane crash, cannibalism, and ninja monkeys. I guess instead of that they compromised on an animated sex sequence, massive fight scene, and pet shark in the sequel. Safe to say, these movies are insane, but the first one really is quite a good rom com.

The start of the Mckay-Ferrel era, Anchorman paved the way for Talladega Nights, Step Brothers, and The Other Guys.

0%
WATERWORKS
95%
comedy
95%
originality
100%
impact
85%
OVERALL SCORE
  • Infinitely Quotable
  • Brian Fantana
  • Career Springboard
  • Over the Top
  • Brick
  • Champ

Best Rom Coms - Anchorman

Conclusion

This movie treats everything, including its romance, like a joke. If you want laughs, it’s for you, if you want love and emotion, maybe not.

Best Rom Com Movies

20. Punch-Drunk Love (2002)

Punch-Drunk Love  •  Phone Rage

Paul Thomas Anderson’s venture into romantic comedy is a bit of a strange one. It involves phone sex, seven sisters, a blue suit, and a lot of chocolate pudding.

Even though we don’t get a ton of time with the love interests and their relationship is a bit confusing, there’s no shortage of charming moments or good filmmaking. Combine that with great Philip Seymour Hoffman and Adam Sandler performances…. And you earn a spot on the list.

60%
WATERWORKS
85%
comedy
90%
originality
80%
impact
85%
OVERALL SCORE
  • Pudding
  • Situational Comedy
  • Phone Hotline
  • Relationship Development
  • Overly Simplified
  • N/A

Best Rom Com Movies - Punch-Drunk Love

Conclusion

Strangely romantic, but also dark, awkward, and funny, a lot is happening inside Barry Egan’s head. It’s unpredictable, sharp, quick, and a unique take on the genre.

Sad Romantic Comedies

19. Sideways (2004)

Sideways  •  Miles Chokes

Alexander Payne follows the melancholy of About Schmidt with more despondence in SidewaysSecuring his control over the depressed man genre.

Luckily, in Sideways, Payne pairs our struggling protagonist with an engaged actor friend trying to get his rocks off. Tie in some Nappy Valley waitresses, an ex-wife, and a 1961 Cheval Blanc, and you get the 05 Best Adapted Screenplay Oscar winner.

Sideways  •  Merlot Clip

Lauded as the best wine movie of all time, the movie both catapulted sales of Pinot Noir while taking some serious slashes at the Merlot grape. If it’s any consolation to Merlot producers out there, Giamatti admits he has no wine knowledge… However, I’d guess screenwriters Alexander Payne, Jim Taylor, and source author Rex Pickett do.

95%
WATERWORKS
80%
comedy
80%
originality
85%
impact
85%
OVERALL SCORE
  • Break-Up Flick
  • Contrasting Characters
  • Napa
  • Misery Porn
  • Snobby
  • Not That Fun

Wine Romantic Comedy Movies - Sideways

Conclusion

More of a break-up than a couple’s movie, Sideways is brutal with its characters. It’s emotional, a little romantic, and funny in bursts but not all the way through.

80s Romantic Comedies

18. Broadcast News (1987)

Broadcast News  •  Love Confessional

The workplace romantic comedy is somewhat of a sub-genre, and perhaps none are better than this film. The newsroom is always a vehicle for office drama, and putting a love triangle in the middle makes it that much better.

Written and directed by rom-com legend James L. Brooks (As Good as it Gets, Terms of Endearment, Spanglish) it was a breakout for Holly Hunter and saw the downfall of newspapers coming long with impressive foresight.

70%
WATERWORKS
85%
comedy
80%
originality
90%
impact
85%
OVERALL SCORE
  • Workplace Romance
  • Love Triangle
  • See-Sawing
  • No Payoff
  • Self-Righteous
  • Airport Cliche

80s Romantic Comedy Movies - Broadcast News

Conclusion

While slightly dated at times, Broadcast News holds its own with any office romance story. It's not the funniest end-to-end but makes up for it with up-and-down romantic swings.

Best Rom Com Movies

17. Wedding Crashers (2005)

Wedding Crashers  •  Lock it Up

Owen Wilson and Vince Vaughn, two masters of the buddy comedy, team up for this fun, at times social inappropriate comedy. The wedding is such a genre staple for the rom-com, Wedding Crashers tackles this head-on and doesn’t miss a beat.

Sure, it contains some typical plot points, but the flip allows this to still feel charming and original. It made Bradley Cooper's career, solidified Rachael Mcadams as a rom com legend, and grossed over $289 million at the box office (good for #2 on this list). It’s a classic romantic comedy in every sense.

90%
WATERWORKS
90%
comedy
90%
originality
90%
impact
85%
OVERALL SCORE
  • Wilson-Vaughn Chemistry
  • Emotional Moments
  • The Rules
  • Mostly Physical Comedy      
  • Artistic Brother Character
  • Wedding Altar Scene

Funniest Romantic Comedies - Wedding Crashers

Conclusion

With a strong balance of laughs and romance, a catchy premise, and great chemistry all around, Wedding Crashers is all you can ask for in a good romantic comedy.

Funniest Romantic Comedies

16. I Love You, Man (2009)

I Love You, Man  •  Golf Clip

After thriving in supporting roles in movies like Anchorman, The 40-Year-Old Virgin, Knocked Upand Forgetting Sarah MarshallPaul Rudd gets to be the lead in I Love You, ManBut it’s no standard romantic comedy.

I Love You, Man flips the genre entirely, focusing on a man’s pursuit of a best man for his wedding. It’s a glimpse into adult bro-dating, Rush fandom, and gym culture.

Sure, it contains some typical plot points, but the flip allows this to still feel charming and original.

60%
WATERWORKS
95%
comedy
90%
originality
75%
impact
85%
OVERALL SCORE
  • Flips Genre
  • Hangout Scenes
  • Quotable
  • Male Centered
  • Alter Cliche
  • Lacks Emotion

Best Rom Coms - I Love You, Man

Conclusion

Definitely a “funny romantic comedy,” I Love You, Man is a bro-mantic comedy. This movie is about male-bonding and hangout scenes.

Great Romantic Comedies

15. The Lady Eve (1941)

The Lady Eve  •  Meet Cute

While the plot is a little hard to get behind, if you roll with the punches, it’s a pretty layered film. The romance is central, and the comedy comes not only through dialogue and action but in editing and plot. 

Basically, a snake expert is also the heir to a fortune. He falls in love with a swindler but leaves once he finds out who she is. She then pretends to be someone else and re-enters his life. They marry, but then she lies to him about all these other men she's been with. In the end, the rich snake expert goes back to the original girl (who is actually the same girl he just married even though he doesn’t know it).

It’s a lot, especially when written out, but makes for an entertaining rom com.

60%
WATERWORKS
80%
comedy
100%
originality
100%
impact
85%
OVERALL SCORE
  • Swindling
  • Accidental Love
  • Supporting Cast
  • Unbelievable
  • Snake Specialist?
  • N/A

Great Romantic Comedies - The Lady Eve

Conclusion

You have to give this the “Clark Kent” benefit of the doubt, but it’s clever and genuinely funny. The best pre-80s watch on the list.

Romantic Comedy Movies

14. Juno (2007)

Juno  •  I’m a Planet

For all of those that wonder what it's like to be pregnant at 17, Juno scratches the itch. It was the small little indie movie that broke out to over $230 million worldwide on a $7.5 million budget.

With a snappy Oscar-winning script (the 3rd Oscar already on this list) and a realistic take on the struggles of teen pregnancy, Juno navigates things like abortion, step-parents, high-school romance, creepy older men, and manages to be funny at the same time.

It’s not a full-blown Rom-Com, as romance is slightly lacking, but it deals a lot with different relationships, all at various stages.

90%
WATERWORKS
90%
comedy
75%
originality
95%
impact
86%
OVERALL SCORE
  • Teenage Perspective
  • Full of Personality
  • Supporting Cast
  • Flashy Music References     
  • Bateman’s Behavior
  • Treatment of Bleeker

Best Rom Coms - Juno

Conclusion

Juno’s strength is in the personality of the protagonist. The subject matter is heavy at times, but always witty, clever, and occasionally touching.

Good Rom Coms

13. Funny People (2009)

Funny People  •  Trailer

Judd Apatow’s underappreciated follow up to The 40-Year-Old Virgin and Knocked Up, Funny People takes a somber look at the life of the stand up comic. Contrasting young ambition with elder regret, Judd Apatow’s films always a “hangout” vibe, but this film maximizes it. Half the scenes are friends ripping on each other and talking about stand-up.

Some may call it overly sentimental, especially about comedy, but it is an authentic glance into that world and has as much depth of any film on this list.

Fun Fact: This is already the 8th straight movie on the list released between 2003 - 2009.

95%
WATERWORKS
90%
comedy
90%
originality
70%
impact
86%
OVERALL SCORE
  •  Yo Teach
  • Great Cast
  • Emotional
  • Self Loathing
  • Airport Cliche
  • Too Long

Good Rom Coms - Funny People

Conclusion

Full of comedians, Funny People isn’t quite as funny as you’d expect. It’s a film about regret, death, and lost romance told through the lens of funny people. But it’s good.

Funniest Romantic Comedies

12. Bridesmaids (2011)

Bridesmaids  •  I Really Want You to Leave

The highest-grossing female R-rated comedy ever ($288 million worldwide), Bridesmaids holds its own with any comedy of the last decade. And while it sways more towards raunch then romance, Chris O’Dowd provides enough Irish charm to warrant its place on the list.

The entire cast brings their A-game with awesome Kristen Wig, Melissa Mccarthy, Rose Byrne, and John Hamm performances. McCarthy, however, steals the show, launching her into comedy stardom.

Oh, also, this was produced by Judd Apatow.

75%
WATERWORKS
95%
comedy
85%
originality
95%
impact
87%
OVERALL SCORE
  • Melissa McCarthy
  • Set Pieces
  • Rivalry Dynamic
  • Predictable
  • “Missing Friend” Sequece
  • N/A

Funniest Romantic Comedies - Bridesmaids

Conclusion

The first female-driven film on the list, Bridesmaids might also be the funniest. That said, it’s more a test of bridal friendship than love, and isn’t a classic romantic comedy.

R-rated Romantic Comedies

11. The 40-Year-Old Virgin (2005)

How to Talk to Women

The plot is in the title on this one, and in retrospect, it looks like an obvious winner. Directed by Judd Apatow and starring newcomers Steve Carell, Paul Rudd, Seth Rogan, Jonah Hill, and to some extent… Kevin Hart, it was Katheern Keener who gave the movie credibility. Crazy.

Ranking extremely high on the memorability scale, it’s the patented Apatow comedy that serves as both hilarious, and surprisingly dramatic.

The 40-Year-Old and grossed $177 million on a $26 million budget. Not bad for a directorial debut.  

80%
WATERWORKS
95%
comedy
90%
originality
95%
impact
87%
OVERALL SCORE
  • Steve Carell Breakout
  • Supporting Characters
  • Fish-Outta-Water
  • Gimmicky
  • Clunky Climax
  • N/A

Romantic Comedy Movies - The 40-Year-Old Virgin

Conclusion

A true romantic comedy, The 40-Year-Old Virgin has the best blend of comedy, drama, and romance so far. It’s a guy's movie but still has a heart.

Top Romantic Comedies

10. The Lobster (2015)

The Lobster  •  Trailer

Alright, now is this movie a Romantic Comedy? Well, it’s about a man searching for love, and it’s certainly funny, so yes.

The most unique movie on the list, Yorgos LanthimosThe Lobster is brash, hilarious, and a bit disturbing from start to finish. Almost every moment of this movie has a tinge of humor, but rarely is it laugh-out-loud funny, it’s subtle, subdued, and quite definitely dark comedy.

If this were a list of “best movies” not “best romantic comedy movies” The Lobster would be higher.

70%
WATERWORKS
90%
comedy
100%
originality
80%
impact
87%
OVERALL SCORE
  • Cinematography/Direction
  • Cold/Dry Humor
  • World Building
  • Potentially Disturbing
  • Romantic Development
  • Lots of Voice Over

Top Romantic Comedies - The Lobster

Conclusion

The Lobster isn't a fun family watch. It’s a strange film. It’s dry, cynical, off-beat, but damn good.

Top Romantic Comedies

9. Knocked Up (2007)

Knocked Up  •  The Day After

Judd Apatow keeps his momentum going with his 4th installment on the best romantic comedies of all time list.

Balancing stoner life, posh Hollywood reporting, and marriage problems, Knocked Up is also full of actors just about to break out (Seth Rogan, Jonah Hill, Jason Segel, Martin Starr, Jay Baruchel, Ken Jeong).

As with all Apatow films, some of the best moments in Knocked Up are the smaller ones, spent working on fleshofthestars.com, or talking to a doorman.

Knocked Up  •  Doorman

It’s one of the funnier films on this list but still packs the ample drama and romance beats. I would be fine with anyone moving this higher. 

85%
WATERWORKS
95%
comedy
80%
originality
90%
impact
88%
OVERALL SCORE
  • Hangout Moments
  • Supporting Characters
  • Seth Rogan Breakout
  • Male Humor
  • N/A
  • N/A

Best Rom Coms - Knocked Up

Conclusion

Judd Apatow knows how to make good romantic comedies, and Knocked Up might be his best. It’s laugh-out-loud funny without sacrificing any piece of the odd-couple romance.

Best Rom Coms

8. Crazy, Stupid, Love (2011)

Crazy, Stupid, Love  •  Just a Divorce

Let's be honest, I was never gonna make this list without putting Ryan Gosling on it. A force in the romance genre, Gosling shows some nice comedic chops in this pairing with Steve Carell.

Our two stars, along with a star studded-supporting cast (Kevin Bacon, Marissa Tomei, Emma Stone, Julianne Moore), weave us through intersecting storylines, love triangles, make-overs, divorces, you name it.

Crazy, Stupid, Love  •  Makeover

Very stylish, sometimes sappy, and perhaps too cool for school at times, Crazy, Stupid, Love dips its toe in a lot of dangerous water but never quite gets burned.

70%
WATERWORKS
90%
comedy
90%
originality
75%
impact
88%
OVERALL SCORE
  • Hot Gosling
  • Mentor-Mentee Dynamic
  • Love Triangles
  • Self-Righteous
  • Overly Stylized
  • Too Coincidental

Best Rom Coms - Crazy, Stupid, Love

Conclusion

The most romance-focused of any film so far, Crazy, Stupid, Love commits to the romantic comedy genre. Boys and girls both should love this one.

BEST ROMantic COMedies list

7. Forgetting Sarah Marshall (2008)

Forgetting Sarah Marshall  •  Peter Meets Aldous

Forgetting Sarah Marshall marks the first glance at Jason Segel in a starring role, and quite the glance it was (wink wink). Segel, also the screenwriter, plays a man who goes to Hawaii to forget his ex, only to run into his ex. Basically, there’s awkwardness at every turn.

Forgetting Sarah Marshall  •  Yoga

Probably the best Hawaii movie ever (maybe the best vacation movie ever), Forgetting Sarah Marshall takes full advantage of the resort setting with comedic bits left and right. Even the saddest moments of this film manage to be funny or lead to a great payoff.

Once again, produced by Judd Apatow. Once again, released between 2003-2009.

80%
WATERWORKS
95%
comedy
75%
originality
80%
impact
89%
OVERALL SCORE
  • Russell Brand
  • Relatability
  • Supporting Characters
  • One-sided
  • Gratuitous Nudity
  • Tropey

Top Romantic Comedies - Forgetting Sarah Marshall

Conclusion

You can’t go wrong here. You get Hawaii, heartbreak, and a heavy portion of laughs. Safe to say, we’re within the top 10 now.

Sad Romantic Comedies

6. Silver Linings Playbook (2012)

Silver Lining Playbook  •  Trailer

Another Oscar winner (Best Actress - Jennifer Lawrence), Silver Linings Playbook undoubtedly leans more into "drom" than "com."

A story about two people battling with mental instability, the comedy comes from supporting characters like Robert De Niro and Chris Tucker, who aren’t in the movie much. Is it enough to make this a rom-com? To me, the final dance sequence tips the scales.

Silver Lining Playbook  •  Dance Scene

This film is well made, well-acted, and has some tremendous moments. It was nominated for 8 academy awards and if this list was about best “movies” instead of “best romantic comedies,” it might climb even higher than #6.

95%
WATERWORKS
75%
comedy
90%
originality
85%
impact
86%
OVERALL SCORE
  • Cinematography/Direction
  • Performances
  • Authentic Philly
  • Not that Funny
  • Predictable
  • Oscar Bait

Good Rom Coms - Silver Linings Playbook

Conclusion

Not a traditional rom-com, but definitely traditional David O. Russel. The city of Philadelphia seeps through every scene in this dramatic, explosive take on the genre. 

Classic Romantic Comedies

5. Rushmore (1998)

Rushmore  •  Trailer

Okay, top 5 now. We’ve officially transitioned from good romantic comedies to great romantic comedies, and it’s hard to find one more charming than this Wes Anderson flick. It’s got:

  • Quirky characters
  • Costumes
  • Depressed people
  • Bill Murray

The romance, however, is a bit unique. Documenting a high-school boy trying to win over a teacher isn’t exactly “love at first sight.” Rushmore is about coming of age, privilege, depression, mourning, and uses this awkward love interest as a vehicle for that.

Bill Murray's deadpan delivery plays terrifically off Jason Swartzman’s boy-scout enthusiasm as comedy bursts from every line and visual in the film.

90%
WATERWORKS
90%
comedy
100%
originality
90%
impact
93%
OVERALL SCORE
  • Established Wes Anderson
  • Love Triangle
  • Theater Scenes
  • Cringey at Times
  • Develops Too Fast
  • N/A

Classic Romantic Comedies - Rushmore

Conclusion

One of Wes Anderson’s best, Rushmore is incredibly charming and touching at the same time. It’s larger than life and enjoyable for anyone to watch.

Best Romantic Comedy Movies

4. When Harry Met Sally... (1989)

Men and Women Can’t Be Friends

An absolute classic, you can’t make a list about the best romantic comedies of all time without it. You certainly can’t make one without talking about Norah Ephron, Billy Crystal, and Meg Ryan, three Rom-Com titans (not to mention director Rob Reiner).

When Harry Met Sally... boasts incredibly witty, quick writing by Norah Ephron who shows a masterful understanding of the male mind. With only 4 major characters (2 male, 2 female), the film is extremely balanced, and we get to know our leads in and out. Most notably, the film grabbed the “Can men and women be friends?” topic before it got cliched and put a stranglehold on it.

90%
WATERWORKS
90%
comedy
100%
originality
100%
impact
95%
OVERALL SCORE
  • Genre Definer
  • Amazing Performances
  • “Friends” Dilemma
  • Sags in 2nd Half
  • Cliched Climax
  • Predictable

Top Romantic Comedies - When Harry Met Sally...

Conclusion

Maybe this should be #1. It’s undoubtedly the best two-sided story on the list, you really get to know these characters and their relationship.

Romantic Comedy Movies

3. 500 Days of Summer (2009)

500 Days of Summer  •  Trailer

Keeping the 2003-2009 trend, 500 Days of Summer was a career catapult, springing star Joseph Gordon Levitt, director Marc Webb, and writers Scott Neustadter and Michael Weber to strong new heights.

It’s a pretty simple story about a boy who falls in love with a girl. The difference comes from a unique non-linear timeline, impressive use of repetition, an awesome split-screen sequence, acknowledgment of genre, and tear-jerking scenes, it’s hard to imagine a better rom com than this one.

100%
WATERWORKS
95%
comedy
95%
originality
90%
impact
95%
OVERALL SCORE
  • Non-Linear Storytelling
  • Relatability
  • Expectation/Reality
  • Male Oriented
  • Supporting Characters
  • N/A

Romantic Comedy Movies - 500 Days of Summer

Conclusion

A modern romantic comedy classic, 500 Days of Summer exceeds everything you can ask for in the genre. It's an exceptionally unique script and will make you cry every time.

Best Romantic Comedies of All Time

2. Groundhog Day (1993)

Groundhog Day  •  French Poetry

What more can you ask for in a movie? We get sour Bill Murray (his 3rd appearance on the list) in a quirky, absurd small town. You could’ve stopped there, the comedic moments in this film are amazing, and the 2nd half love story holds up with the romantic beats of any rom-com.

Unfortunately, the Groundhog Day device (relieving the same day over and over) has itself been used over and over again in recent years. None have come close to topping the original.

80%
WATERWORKS
100%
comedy
100%
originality
100%
impact
95%
OVERALL SCORE
  • Trend Setter
  • Peak Murray
  • Small Town Fun
  • Gimmicky
  • Unbelievable Relationship
  • N/A

Best Romantic Comedies of all Time - Groundhog Day

Conclusion

It starts as a straight comedy and surprises with a great romance. An absolute classic, if you like Bill Murray and haven’t seen this do yourself a favor and remedy that ASAP.

Best Romantic Comedies of All Time

1. Annie Hall (1977)

Annie Hall  •  Honest Subtitles

The oldest and best film on the list, Annie Hall is a Romantic Comedy that won four Oscars! Four! Including Best Picture, Best Actress, Best Director, and Best Original Screenplay. It’s no secret the screenplay voters like good rom coms, but Best Picture!

Woody Allen was so ahead of his time with his talking head footage, meta aspects, critiques of Hollywood, the sour main character, the non-storybook ending. The influence of this film is unprecedented.

Annie Hall  •  In Line

Still, even if you just look at the movie itself, it’s so unique.  It feels one-of-a-kind, like a history of Woody Allen's life. It’s not made for a studio or an audience, it’s made for him.

70%
WATERWORKS
95%
comedy
100%
originality
100%
impact
91%
OVERALL SCORE
  • Tremendously Self-Aware
  • Amazing Writing
  • Iconic Moments
  • One-Sided
  • Anti-Climatic
  • N/A

Best Romantic Comedies of all Time - Annie Hall

Conclusion

It’s seminal rom com and it will never be topped. Be prepared for a lot of neurosis and self-deprecation, but know that this is a masterpiece.

UP NEXT

Best Romantic Movies Ever

Now that you know the best romantic comedies of all time, what’s next? Maybe you want more romance and less comedy? Up next is our ranked list of the most romantic movies ever made. From Casablanca to La La Land and everything in between, it’s time to continue our cinematic romance tour.

Up Next: Romantic movies ranked →
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