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25 Great Romantic Comedies That Are Worth Your Time

07 October 2015 | Features, Film Lists | by Brian Thompson

best romantic comedies

Romantic comedies too often get a bad rap, especially among male viewers. Sure, there are some films with this label whose cheesy dialogue and lack of realism make them almost unwatchable, but there are plenty of clunkers that can be found in any film genre.

Still, there are others that come along to remind us why we enjoy the movies: the naïve vulnerability, the sincere humanity, and the brief escape from reality. So much of human nature is captured within the frames of these films, yet they are often overlooked in favor of more gripping dramas or unadulterated slapstick amusement. As romantic comedies ride the line between the two genres, they offer a more realistic view of existence – even at their most outrageous.

In an attempt to step on as few toes as possible, this list is ordered chronologically rather than in order of importance.

 

1. Bringing Up Baby (1938)

bringing up baby

An argument could be made that Susan Vance was the first “manic pixie dream girl” in cinema history. After being slammed by critics following a series of box office flops, Katherine Hepburn delivers a performance that is a harmonious blend of boisterous and vulnerable in what is has become one of her most celebrated roles.

Bringing Up Baby gives birth to all of the shameless whimsy of screwball comedies and all of the glamorous romance of the golden age of Hollywood. The pairing of Hepburn and Cary Grant formed a pure, cohesive chemistry that is still trying to be replicated to this day. Even among a filmography as devoid of blemishes as Howard Hawks’s is, this masterpiece stands out. Plus, you’ve got to admire the arrogance and lunacy that had to exist to film on set with a live leopard.

 

2. The Apartment (1960)

The Apartment (1960)

Billy Wilder had already cemented his place in the hearts of cinema lovers with well-loved classics like Sunset Boulevard and Some Like It Hot, but he directed a very different kind of movie in 1960. Whereas most of his work had fallen primarily into either the comedy or drama camps, The Apartment blended the two genres so seamlessly that it felt as if it were truly capturing the reality of the era.

The jokes land perfectly, but there are moments when C.C. Baxter (played beautifully by Jack Lemmon) faces absolute despair. In the midst of the discussion of loneliness, Wilder shines a light on misogyny and gender politics in the workplace. This is a movie that reminds us that while comedies are meant to entertain, there is no reason why they can’t start more serious conversations.

 

3. Harold and Maude (1971)

harold and maude pic

In one of the least conventional efforts on this list – particularly for its time – this black comedy reflects the eccentricities and rebellion of the cinema of the 1970’s. Harold’s morbid obsession with death, displayed by his elaborate fake suicide attempts and his fascination with funerals, can be interpreted as a dissatisfaction with the state of humanity. He is able to find a kindred spirit in Maude, who has a similar intrigue for the macabre.

In circumnavigating the social barriers of age, the two are able to find joy in life through the company of one another. Truly, this is a film that fully examines why people are drawn to one another, rather than forcing two unlikely characters into a brief romance. The existential themes mixed with the acoustic soundtrack by Cat Stevens have solidified Harold and Maude’s cult status as the film, much like Maude, has only improved with age.

 

4. Annie Hall (1977)

Annie-Hall-1

There is a reason why this is Woody Allen’s most praised film. Annie Hall tells a realistic love story full of wit and humor, but it does so in an unconventional way. Expectations of the viewers are shattered as Allen breaks the fourth wall to complain to us about his relationship troubles, as characters have conversations with their former selves, and as the focus jumps between time and space without warning or explanation.

Allen also shows a much more serious side of himself than he had in his previous slapstick films, making statements about gender stereotypes, cultural identity, and the nature of human happiness. Ranking among the director’s most delicately crafted works, Annie Hall doesn’t have a line of dialogue that is out of place and it bites just as deep today as it did when it was released in 1977.

 

5. The Princess Bride (1987)

The Princess Bride

In what is easily one of the most quotable movies of all time, Rob Reiner beautifully adapts William Goldman’s classic novel into a film that is required viewing for many pop culture references. The overwhelming charisma and universal themes of this movie allow just about any viewer to find pieces of themselves within its frames.

Since the story is being told from an outside party, the tone is able to shift as the boy and his grandfather argue over what makes for a compelling tale. This allows the viewer to place themselves in the shoes of either character, depending on where they find themselves in life, and see this magical world through their eyes. The Princess Bride defies conventional genre expectations and creates a world that is as inviting as it is prophetic.

 

6. Say Anything… (1989)

say-anything

All of the greatest films explore concepts that are applicable outside of the genre. Say Anything… deals with the aimlessness of youth – particularly in determining a career pathway – as seen through the eyes of both the slacker and the overachiever.

The film strays from the typical romance tropes by giving us characters that are innately recognizable for being deeply genuine. Cameron Crowe’s directorial debut doesn’t play out like a Hollywood glamor piece; it is a film that works because of its ability to harness reality and allow the audience to uncover meaning for themselves, rather than taking a stance of moral authority.

Lloyd Dobler represents the anxious and overwhelmed voice of the MTV generation as they define who they are outside the confines of their parents’ homes. The tremendous sincerity of this movie catapulted John Cusack into stardom and convinced audiences everywhere to go out and buy a Peter Gabriel cassette.

 

7. When Harry Met Sally… (1989)

when-harry-met-sally-1989

This is the movie that set all of the standards and conventions of the genre that the rest of the movies on this list either embraced or destroyed. When Harry Met Sally… takes a deeper look of the complicated anguish that accompanies relationships. In a movie that can be uproariously funny and also establishes a tender warmth, Rob Reiner again shows his extraordinary ability for shifting tones without betraying the essence of either one.

The cutaways to the older couples recounting their first encounters with each other marvelously display the universality of love across cultures. Billy Crystal and Meg Ryan are able to construct a repartee that is both hilariously witty and strikingly believable. When Harry Met Sally… perfectly captures the work and passion involved in creating and maintaining a successful romantic relationship.

 

8. Groundhog Day (1993)

groundhog-day

It would be entertaining seeing just about anyone fated to relive the same day over and over, but Bill Murray uses his brilliant comedic timing and piercing wit to create a performance that is both memorable and poetically poignant. Countless viewers will be able to relate to the feeling of hopelessness that comes with monotony, even if they don’t get the satisfaction of uninhibited action without consequence.

While this movie is accessible and aims to please a varied audience, it poses some extremely heavy philosophical questions. We see Phil’s approach to the situation stretch the entire range of the spectrum, whether he is using his predicament to take advantage of women or he is falling into destructive despair. Groundhog Day demonstrates the difficulty to live in the moment, especially when you don’t feel that you are able to make an impact on your surroundings.

 

 

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  • Muntaser Ibrahim

    Enough Said?

  • Flopi

    Forgetting Sarah Marshall, I love you, man and crazy, stupid love are really bad movies. Like, terrible. What about a lot like love? That one is better. Love actually is the best

    • Steppenwolf

      “I love you, man” is super great?!

    • GL

      Crazy, Stupid Love is the best!!! Agree on the other two though

  • Hatesville

    Did I miss Before Sunrise?

    • Fabrizzio Andres Zevallos Ruiz

      Comedys

  • Klaus Dannick

    Zack and Miri Make a Porno!!!

  • luke

    Curtis’ Notting Hill is possibly one of the most beautiful romantic comedy films I’ve ever seen…. it should be included … instead of Love actually in my opinion… one of Curtis’ worst films… (i think)

  • frank mango

    what is lost in translation considered ?

  • GL

    Fairly tragic list… and I am a major closet rom com fan

  • Ted Wolf

    I’m glad we threw a bone to a screwball comedy (get it? bringing up baby? my intercoster clavicle?) but really, Nothing Sacred, It Happened One Night, My Favorite Wife and fast forward to all the Day/Hudson pairings.

  • Stephus

    Princess and the warrior!!!!

  • Brett Fillmore

    When I saw Love Actually I refused to read any further.

  • Andres Abad

    If 500 days of Summer its on this List… why isnt Eternal Sunshine of the Spotless mind ? Come on.. i know its not the kind of romanticism everyone try to find on a movie but.. to me, this one was one of the best romantic comedies that i can remember. Even though is chaotic and somehow pretty depressing but come on.. that`s what love is

  • Pingback: 25 Great Romantic Comedies That Are Worth Your Time « Taste of Cinema | GoGoAnimes.com()

  • Dave Nosanaj

    “Los Amantes del Círculo Polar” is missing

  • Rich G

    First of all well done for including Away we go it is the only rom com I have ever seen that is good. Its hysterically, funny, inteligent and genuinely romantic, which are all factors missing from most rom coms. Most rom com’s are typically not romantic or funny. It’s a genre I have always found odd as the humour is simplistic and cheap and the romance synthetic and false. This list seeks to refute that as some of these films are not really rom com’s!
    Rom coms are banal films that appeal to clichéd social stereotypes of of a females fantasy man. With all the low brow condescending nonsense that goes with it. They typically demean woman (the viewer and the lead actress). Some of these fit the bill. But many such as Hi fidelity, Harold and Maude and Groundhog day are not Rom Com’s. A Rom Com is defined by the romance and comedy being central to driving the narrative. The film is built around that. Hi fidelity is a comedy drama about a man’s life experiences. Yes it includes relationships etc but that is not the central theme. Again Harold and Maude simply wtf I have no idea what your logic is. Groundhog day is a clever comedy about how mundane and repetitive life can become and how cynical we can become. With some clever philosophical questions. The romance is secondary to the this, hence not a Rom Com. You really need to learn what the definition of Rom Com as a genre is!

  • Rich G

    First of all well done for including Away we go it is the only Rom Com I have ever seen that is good. Its hysterically, funny, inteligent and genuinely romantic, which are all factors missing from most Rom Coms. Most Rom Com’s are typically not romantic or funny. It’s a genre I have always found odd as the humour is simplistic and cheap and the romance synthetic and false. This list seeks to refute that as some of these films are not really Rom Com’s!
    Rom coms are banal films that appeal to clichéd social stereotypes of a females fantasy man. With all the low brow condescending nonsense that goes with it. They typically demean woman. Some of these fit the bill eg when Harry Met Sally or Sleepless in Seattle AKA You’ve Got Mail . But many such as Hi fidelity, Harold and Maude and Groundhog day are not from coms. A Rom Com is defined by the romance and comedy being central to driving the narrative and the film is built around that. Hi fidelity is a comedy drama about a man’s life experiences. Yes it includes relationships etc but that is not the central theme. Again Harold and Maude simply wtf I have no idea what your logic is. Groundhog day is a clever comedy about how mundane and repetitive life can become and how cynical we can become. With some clever philosophical questions. The romance is secondary to this, hence not a Rom Com. You really need to learn what the definition of a Rom Com as a genre is!

  • Luigi Vampa

    First of all, where’s the hell is ”Eternal Sunshine’? Also, would you consider ‘Adaptation’ and ‘Her’ rom coms?

    • Lio Mustoni

      I don’t think any of those can be considered comedies, at all. They’re romantic dramas at best. But they are great movies, that’s for sure.

  • Cygnifier

    I like your approach to the title and ordering! A few other films to consider from the Golden Age of Hollywood: It Happened One Night (1934) — 1st movie to sweep the major Academy Awards; His Girl Friday; My Man Godfrey; and Philadelphia Story. There are a number of wonderful Bollywood romantic comedies as well.

  • JCRM

    Nocked up? forgetting sarah marshall? what! and.. pretty in pink? 10 things about you? There´s something about mary? Bridget Jones? Amelie?? 50 first dates?? While you where sleeping? Serendipity? and Grease???? OR NOTTING HILL!!!?!?!?!?!

  • Richard McLin

    No sixteen candles
    Definitely, Maybe
    Wedding Singer
    My Big Fat Greek Wedding
    Pretty Woman
    Runaway Bride

  • Ollie

    Flaw!

  • Lio Mustoni

    Good Dick
    Singles
    The Artist
    In Search of a Midnight Kiss
    Punch Drunk Love
    Once
    Grosse Pointe Blank

    Some that come to mind that didn’t quite make the list, and deserved to.

    • filipecoutinho

      SINGLES!!!!!

  • Klaus Dannick

    Zack and Miri Make a Porno!!!

  • Charlie Watson

    I appreciate the inclusions of Crazy, Stupid, Love and What If on this list. CSL is one of my favourite films ever and What If is one of those “modern rom coms” where it’s a bit cliché but it stands out by doing something different at the same time. Man Up is another excellent example.

  • LilyG95

    I feel like I’m the only person who prefers You’ve Got Mail to Sleepless in Seattle. There’s just something about Tom Hanks playing a lovable prick that I enjoy immensely.

  • Jack Napier

    A film never mentioned but I thought was good for a rom com was Sleeping With Other People