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The Best Romantic Comedies
The Best Romantic Comedies

Film

The Best Romantic Comedies

The Greatest Romantic Comedies Part 1

We all have predisposed notions about the infamous “romantic comedy.” As with other genres, there’s a large subsection of offerings, giving it a bad name. But, for every tired, cliché-driven comedy, there is another impressive offering that redefines the genre, garners plenty of laughs, and tells an honest story about love and relationships, however warped they may be. In this article, we’ll take a look at the fifty romantic comedy films that should be seen. These may not all be classic films, but they certainly put a stamp on the industry and the genre we affectionately call “rom-coms.”

 #50. Moonrise Kingdom (2012)

Most of Wes Anderson’s films could be described as romantic comedies, but his 2012 effort stands out, as its central story focuses on young love and the need to find acceptance. In Anderson’s world, while quirks abound, true connections between characters are commonplace. With Moonrise Kingdom, Anderson chose two child actors to lead his film, Jared Gilman and Kara Hayward, as they run away together through an Anderson-esque version of New England. While the film adds a bevy of Anderson regulars (Bill Murray, Jason Schwartzman) and new additions (Tilda Swinton, Edward Norton) to the universe, his ever-present focus on these two youths is what makes the film a testament to storytelling. There isn’t a second of the relationship between Sam and Suzy that doesn’t feel genuine, in its own outlandish, pastel way.

#49. That Obscure Object of Desire (1977)

Director Luis Buñuel made a career of creating absurdist cinema. From his famed collaboration with Salvador Dali, Un Chien Andalou on, Buñuel consistently criticized the class system through his adventures in filmmaking insanity. For his final film, Buñuel turnd his camera onto the absurdity of romantic obsession with Cet obscur objet du désir (That Obscure Object of Desire). Centering around an aging Frenchman Mathieu (Fernando Rey) and a beautiful Spanish dancer named Conchita, it is told almost entirely in flashback, as we see how Mathieu has been brought to wit’s end by Conchita and his obsession with her. While it sounds, on the surface, like a typical rom-com, Buñuel refuses to be underestimated, casting two separate women (Carole Bouquet and Angela Molina) as Conchita, who look and act nothing alike. They never appear in a scene together, but play Conchita in various pieces of the story. Buñuel’s probably right – we fall madly in love, but can’t remember the exact person who brought us to our knees.

#48. The Wedding Singer (1998)

Romantic comedies have a habit of putting the same story in different time periods, then juicing up the meta humor to say “Look how different things were. Isn’t it funny?” None may have done it better than The Wedding Singer,  the first film to give Adam Sandler a role that showed the mild range he would later realize in Punch Drunk Love. Sandler plays the title singer, Robbie, a idealistic musician who can’t seem to catch a break. Enter Julia (Drew Barrymore), a new waitress who Robbie quickly falls for as she plans her own wedding. One-dimensional characters abound and topical 80′s humor overshadows most of the film’s aspects, but the first pairing of Sandler and Barrymore reveals a chemistry they would try to duplicate multiple times going forward, for diminishing results. Here, they do it right, despite the overly sappy elements of the film. Besides, Billy Idol is in it.

Silver Linings Playbook (2012)

#47. Silver Linings Playbook (2012)

Detractors  be damned: David O. Russell’s 2012 foray into rom-coms worked on enough levels to escape from the “crazy characters fall in love” trash heap. Headlined by Bradley Cooper and Jennifer Lawrence in her Oscar-winning role, Silver Linings Playbook details Pat Solitano’s (Cooper) return home after a stint in a mental ward, determined to get well simply by eating right and exercising. Through extenuating circumstances, he ends up striking a deal with Tiffany (Lawrence), agreeing to help her in an upcoming dance competition if she helps him try to reconcile with his wife. The film goes where you expect it to go, but Cooper and Lawrence give phenomenal lead performances, along with fine supporting turns from Robert De Niro and Jacki Weaver. It’s not a prestige film by any means, but an example of what a rom-com can be if it’s written and directed well and the actors go for broke.

#46. The Shop Around the Corner (1940)

Long before Meg Ryan had to close her bookstore thanks to money-hungry Tom Hanks and you could have a romance over instant messenger, Ernst Lubitsch produced and directed this adaptation of the Hungarian play Parfumerie by Miklós László. The Shop Around the Corner stars James Stewart as Alfred, the top salesman at a local gift shop, who argues with his boss over the sale of a cigarette box. After their disagreement, Klara (Margaret Sullivan) enters the shop, looking for a job. After she successfully sells one of the boxes, she is hired and a rivalry forms between Alfred and Klara. Simultaneously, Alfred tells his friend that he has been anonymously exchanging letters with a woman he found in the newspaper. As you can guess, Klara is this mysterious woman. It seems old hat now, but in 1940, the secret-admirer romantic comedy had yet to get its day in the sun, until this little gem hit the screens. It was remade by Nora Ephron in 1998 as You’ve Got Mail – a good movie in its own right. But it’ll never touch the original.

High Fidelity (2000)

#45. High Fidelity (2000)

The first of writer Nick Hornby’s novels to come to the screen, High Fidelity stars John Cusack as Rob Gordon, a recently dumped record store owner recounting all his failed relationships in an attempt to figure out what he’s doing wrong. Paired with his contempt for popular music and his “musical moron twins” (Jack Black & Todd Louiso), he spends his time making music-themed lists and ridiculing customers who don’t share their tastes. Eventually, he sets his sights on reconciling with his most recent ex Laura (Iben Hjejle), trying to figure out ways to win her back. Directed by Stephen Frears, High Fidelity finds a wonderful balance between the two sides of Rob – a self-indulgent snob and a needy man-child. As always, Cusack walks a fine line between likable and unlikable, but manages to get the audience on his side as he tries to piece together a life full of loves lost and lack of self-realization. Few films can embed a soundtrack into a rom-com, but refuse to let it overshadow the story the way this one does.

#44. Clueless (1995)

If Jane Austen moved to Los Angeles, the result would be this Amy Heckerling romantic comedy. Clueless, based on the Austen novel Emma, takes us into the life of Cher (Alicia Silverstone) as she navigates Beverly Hills in her designer clothes and good looks. Standing at the top of her popularity empire, Cher plays matchmaker for the new girl Tai (Brittany Murphy), only to find her schemes unsuccessful. All the while, she bickers with her ex-stepbrother Josh (Paul Rudd), setting the stage for the slow burn that becomes their “courtship.” Let’s not split hairs – Clueless is lightweight, sometimes stupid, and a little full of itself. But it’s also supremely entertaining and gave birth to a laundry list of terminology that made itself into the American lexicon in the mid-1990′s. It may only be loosely inspired by Austen’s work, but don’t ignore the fact that love and friendship haven’t changed all that much since the 1800′s.

As Good As It Gets (1997)

#43. As Good As It Gets (1997)

James L. Brooks made a career writing brilliant screenplays for both movies and television, but has only sporadically stepped behind the camera as a director. In 1983, his film Terms of Endearment swept the Oscars with Brooks taking home Best Director and Adapted Screenplay. But it wasn’t until 1997 that he would make another Oscar-winning film, with As Good As It Gets. The strange pairing of Jack Nicholson and Helen Hunt certainly made for interesting conversation, but at the center of it all was Nicholson’s performance as Melvin, an author with a serious case of OCD, who hates almost everyone. Melvin becomes a fully conceived character thanks to his involvement with Hunt’s Carol, his gay neighbor Simon (a career high for Greg Kinnear), and, of all things, Simon’s dog. A strong script, meticulous direction, and plenty of funny lines of dialogue make this romantic comedy a necessary venture.

Shakespeare in Love (1998)

#42. Shakespeare in Love (1998)

So, what does it take to beat a Steven Spielberg-directed, Tom Hanks-starring film about World War II? A British romantic comedy/drama about William Shakespeare (Joseph Fiennes) and his love affair while writing Romeo and Juliet. This Best Picture winner, directed by John Madden, tells a fictionalized story of Shakespeare, as he rises from a poor playwright to a literary legend, thanks, in part, to his falling in love with, ironically, a woman who auditioned for the role of Romeo in another play. Viola (Gwenyth Paltrow) inspires him to completely rewrite the play, eventually becoming his most famous work. Shakespeare in Love will long be remembered as the film that beat Saving Private Ryan, but look again: this is a well-written, well- acted story that deserves a better reception that it has historically received in critic circles.

Amélie (2001)

#41. Amélie (2001)

The full French title is Le Fabuleux Destin d’Amélie Poulain, but English-speaking audiences know it as Amélie. Starring Audrey Tautou in her star-making role, Amélie follows the title character as she navigates a world of wonder, thanks to her incredible imagination. Having been raised by eccentric parents who sheltered her from other children, she goes on a quest of discovery after she finds a metal box of memorabilia left by a previous tenant. She decides to track him down to return the box. What results is a strangely episodic, wondrous film that moves from character to character, with Amélie being our eyes and ears. While the film does not really begin as a love story, exactly, we slowly see Amélie evolve as she meets more and more people and finds more and more beauty in the world outside of her imagination. We all may end up in love with someone else, but we must first love our world as it stands on its own.

Groundhog Day (1993)

#40. Groundhog Day (1993)

Bill Murray was nominated for an Oscar after his dramatic turn in Sofia Coppola’s Lost in Translation. He has shown great promise in Wes Anderson’s films. But his best performance to date came in this Harold Ramis comedy about a man who can’t escape February 2nd in Punxsutawney, Pennsylvania. Starring as Phil, a weatherman in Pittsburgh sent to cover the Groundhog Day festivities in the tiny Western Pennsylvania town, Murray shows a range beyond any of the screwball or deadly serious work he’s done. As Phil gets trapped in a time warp that repeats the same day over and over, we see a man go through all the stages of grief – denial, anger, bargaining, depression, and acceptance. It isn’t until Phil realizes that being a good person isn’t about what it does for you that he sees his tomorrow with Andie MacDowell’s Rita. An existential love story if ever there was one, Ramis and Danny Rubin’s screenplay is still one of the best ever.

#39. Knocked Up (2007)

Judd Apatow was building his empire of stoner comedy and gross out humor when one of his better efforts premiered in 2007. Knocked Up stars Seth Rogen as a slacker named Ben who manages to land a one-night stand with rising E! journalist Allison, played by Katherine Heigl. The resulting pregnancy and forced courtship is hilarious, despite the criticism of the film and the accusations of it being sexist (including plenty from the leading lady). It’s not a mystery – this is a movie about a pregnancy that doesn’t focus on the woman. Not only that, she is without a doubt the least interesting character in the film. Regardless, Apatow’s film boasts a funny script, solid performances, and has stood up as one of the better films of his catalog.

#38. Adam’s Rib (1949)

In 1949, George Cukor directed two screen legends, Katharine Hepburn and Spencer Tracy, in Adam’s Rib, a story of two married lawyers representing either side of a court case involving a woman shooting her husband after catching him cheating on her. Obviously, in this scenario, Adam (Tracy) sides with the man, while Amanda (Hepburn) sides with the woman. What ensues is a screwball battle of the sexes, involving fiendish pranks and various attempts at litigation and gaining the upper hand on the other. Eventually, the case takes its toll on their relationship. Tracy and Hepburn were never married in real life, but had a private affair that lasted 26 years, leading to them being paired up in numerous films. Adam’s Rib was just another example of two of the greatest actors in film history and how much easier it looks when the two leads have a real, honest connection. It’s tough to fake real love.

Harold and Maude (1978)

#37. Harold and Maude (1978)

Director Hal Ashby’s second film, Harold and Maude, was more black comedy than romantic comedy. Despite that, the story of a surprising pair of companions elevates beyond the typical romantic comedy tropes. Starring Bud Cort as Harold, a young man obsessed with death, the film sees him drifting away from his life and into a relationship with a 79-year-old woman names Maude, played by Ruth Gordon (oddly enough, Gordon was a screenwriter for Adam’s Rib). Ruth teaches Harold about the need to embrace life and live it to the fullest, something he has never felt the need to do. Somehow, their relationship blossoms into a romantic one, despite their incredible age difference. It’s a one-of-a-kind romance that works thanks to the performances of Cort and Gordon. Hey, the heart wants what the heart wants.

Chasing Amy (1997)

#36. Chasing Amy (1997)

From age difference to sexual orientation difference, Kevin Smith’s third film remains his most interesting and effective, centering around a comic book artist named Holden (Ben Affleck) and his relationship with another comic book artist named Alyssa (Joey Lauren Adams). After Holden and Alyssa become good friends, he slowly realizes that he’s falling for her. Unfortunately for him, she’s a lesbian. Where the film goes from there is previously unmarked territory, as it explores sexuality and love in a way not really seen in many mainstream films before then. But while the relationship blossoms, we see Holden’s business partner Banky (Jason Lee in his best performance) slowly begin to lose touch with his friend, turning that anger toward Alyssa, adding another layer to the complicated relationship. Extremely crude and straight-forward about sex, Chasing Amy found a niche by exploring how important history is to relationships and how it defines you as a person.

Moonstruck (1987)

#35. Moonstruck (1987)

Before he became wildly unpredictable, Nicolas Cage laid the groundwork to be a pretty successful comedic actor, with work in Valley Girl and Raising Arizona. In 1987, Cage turned in his first performance to get him on the Oscar radar in Moonstruck. The Norman Jewison-directed film centers around Loretta (Cher in her Oscar-winning role) as she falls in love with the brother (Cage) of a man she had agreed to marry (Danny Aiello). In essence, it’s a simple love triangle, but with a cartoonish Italian spin.  The film grabbed six Oscar nominations, four of them for acting. The screenplay grabbed an Oscar victory for John Patrick  Shanley, who wouldn’t get nominated again until 2009, with Doubt. For years to come, the film (and Cher’s movie career) will always be summed up by one line: “Snap out of it!” Sums up Cage’s career lately, too.

#34. Sense and Sensibility (1995)

Long before Ang Lee caught the American public off-guard with Brokeback Mountain, he directed the best theatrical adaptation of a Jane Austen novel, 1995′s Sense and Sensibility. Starring (and written for the screen by) Emma Thompson, the film took Austen’s prose and, while not staying completely faithful, translated it into a beautifully shot, whimsical story of love in the life of two polar opposite sisters. Also starring a pre-Titanic Kate Winslet, Alan Rickman, and Hugh Grant at his most charming, Sense and Sensibility may be best described as an exercise in delight – by the end of the film, if you aren’t smiling, you probably have no soul.

Manhattan (1979)

#33. Manhattan (1979)

Woody Allen is Woody Allen. His films are idiosyncratic and his stories are microcosms of an overwhelming sense of self-loathing. At the same time, he really knows how to create characters. Probably the best job he did as a director came in 1979 with Manhattan, the story of a divorced New York man (Allen) dating a high schooler (Oscar-nominated Mariel Hemingway), but slowly falling for his friend’s mistress (Diane Keaton). Filmed in black and white, Manhattan lays Allen’s typical neurosis over a beautifully shot New York City better than any of his other films have done since. It’s a funny film, but it’s also one of Allen’s most realistic portrayals of life and love in the big city. The acting feels more natural than many of his other efforts and the connection formed between Allen and Keaton on screen is as genuine as ever. But, first and foremost, this film is in love with the Big Apple.

Splash (1984)

#32. Splash (1984)

After Tom Hanks gained semi-fame in TV’s Bosom Buddies, he made his first big splash (pun very much intended) in this 1984 fantasy romantic comedy about a man who reunites with the mermaid who saved his life when he was a child. Directed by Ron Howard, Splash spotlighted Hanks’ comic timing and Everyman likability, while also proving he could carry a film. It didn’t hurt to throw in great supporting performances from John Candy and Eugene Levy, a supermodel (Daryl Hannah) to play the mermaid, and an Oscar-nominated screenplay. As a bonus, it was the first film released by Disney under their offshoot production company Touchstone Pictures, essentially becoming the first film Disney produced that wasn’t specifically geared toward children.

 Four Weddings and a Funeral (1994)

#31. Four Weddings and a Funeral (1994)

A year before Hugh Grant stole hearts as Edward Ferrars in Sense and Sensibility, he won his first (and only) Golden Globe for his performance in Four Weddings and a Funeral, a Mike Newell-directed, Richard Curtis-written episodic romp through wedding after wedding, following Grant’s Charles, as he keeps running into an American woman named Carrie (Andie MacDowell) at each event. As he always does, Grant puts on his “bachelor lifestyle” face and eventually gets broken down, always putting on the charms he needs to, despite how confused and awkward he seems to be. In any case, the sharp British wit stands out as the star of the film, another indication that Curtis knows how to write a romantic comedy well, especially for British audiences. Nominated for Best Picture in one of the best years for movies ever (Pulp Fiction, The Shawshank Redemption, and more), it still manages to stand out on its own.

As we approach the halfway point, we’ll see films that run the gamut from a love story that deliberately states it’s not a love story to a sports-themed rom-com to another Richard Curtis-penned movie. We hope you’ve enjoyed the ride so far; it only gets better from here.

*****

We’ve reached the near mid-point of this Definitive List; 20 down, 30 to go. As we move forward, the story of “boy meets girl” becomes more complicated, as plenty of stumbling blocks stand in the way: lack of experience, insecurity, unsupportive parents, and, as in most cases, ego. So, when we watch all these films, what do we learn? Hundreds of romantic comedies end happily, but none end in the same way. Perhaps there’s a method to the madness, but the more we tread through these highlights, the more it’s clear that to make an impact, you have to change the game or perfect the existing one.

Bull Durham (1988)

#30. Bull Durham (1988)

Baseball movies had worn out their welcome a bit in the mid-80s and audiences weren’t clamoring for a romantic comedy based around the national pastime. Enter writer/director Ron Shelton, who decided to write a film based on his experiences in the minor leagues. The movie was Bull Durham, the story of a baseball groupie named Annie (Susan Sarandon) and her yearly goal to seduce one of the players on her local team, the Durham Bulls. As she romances stud pitcher Nuke LaLoosh (Tim Robbins), she slowly starts to fall for veteran catcher Crash Davis (Kevin Costner), brought in to teach LaLoosh the art of the game. After the dust settled, Bull Durham offered up more laughs than any other baseball movie and provided a solid love story behind it, thanks to the chemistry between Sarandon and her two leads. It will always stand up as a great film for fans of baseball, love stories, and anyone who believes in long, slow, deep, soft, wet kisses that last 3 days.

#29. Eternal Sunshine of the Spotless Mind (2004)

It’s not the funniest romantic comedy, but this film is funny enough to fall into that shaky category. It’s one of the most original, that’s for sure. When Joel (Jim Carrey) finds out his ex-girlfriend Clementine (Kate Winslet) had him erased from her memory, he decides to do the same to her, slowly traveling through his memory of their courtship and learning why, despite the bitter end, its existence should be sustained. Teaming director Michel Gondry with screenwriter Charlie Kaufman will always produce fascinating results, and Eternal Sunshine is one of the most critically loved films of the past 20 years, thanks to the imaginative writing, daring direction, and brilliant lead performances from Winslet and Carrey, at his career best. It doesn’t hurt to have a supporting cast including Tom Wilkinson, Kirsten Dunst, Mark Ruffalo, Elijah Wood, and David Cross, either.

There’s Something About Mary (1998)

#28. There’s Something About Mary (1998)

Let’s get dirty for a moment. For years, the “romantic comedy” sat in the realm of PG and PG-13, never really fraying from that rating. That is, until the Farrelly brothers decided to put a grossout spin on it. It had been raunchy before, but never this raunchy. There’s Something about Mary took budding star Cameron Diaz and made her a household name, as the object of desire for a bounty of men, namely Ben Stiller’s Ted and Matt Dillon’s Healy. Ted finally gets to date Mary years later, after a disastrous high school experience with her involving a stray zipper. He hired Healy to track her down, only to see him also fall for Mary. The movie takes ridiculous twists and turns, as more and more possible suitors for Mary reveal themselves, including NFL star Brett Favre. The Farrellys managed to take the old trope of an old flame reemerging and spun it on its head, adding plenty of fart jokes and f-bombs along the way.  Most importantly, we’ll never look at hair spray the same again.

#27. The Seven Year Itch (1955)

Billy Wilder (who appears plenty more on this list) made a career out of the clever romantic comedy. In 1955, he worked with the world’s favorite pinup girl Marilyn Monroe, for The Seven Year Itch, a silly rom-com about a man’s mid-life crisis. Richard (Tom Ewell) is a publishing executive who meets an actress who rents an apartment upstairs from him. His psychiatrist had informed him of the concept that a large percentage of men tend to have affairs in the seventh year of marriage, so he sees this as “normal.” A good portion of the film involves Richard’s fantasy conversations with his wife and his strange, imagined irresistible nature. Wilder had to be discrete – according to production codes, he couldn’t actually show a man committing adultery. Of course, Richard eventually comes to his senses, but not before this well-received rom-com gave us one of cinema’s most memorable images, with Monroe standing over a subway grate. For that image alone, it belongs on the list.

The 40-Year-Old Virgin (2005)

#26. The 40-Year-Old Virgin (2005)

Eight years after the Farrelly brothers brought off-kilter humor to the romantic comedy and the mainstream, Judd Apatow emerged from years of critically acclaimed, yet commercially ignored work to co-write, produce, and direct The 40-Year-Old-Virgin. Starring Steve Carell, the film shows the life of Andy, a friendly, but socially ignorant middle-aged man who has yet to experience one of life’s greatest pleasures. What makes this film a success is the funny, yet honest portrayal of the dual importance/unimportance of sex in a relationship and how missing out can make you both a warped and well-rounded individual. Andy’s romance with Trish (Catherine Keener) is touching and believable, but what sets the film apart is how Andy’s “friends” are the ones who eventually go through as much growth as the lead couple. Plenty of throwaway jokes abound (as in all Apatow films), but the emotional core is what makes this one his most affecting.

NEXT | PART TWO

Editor’s Note: This article was originally published under our old brand, Sound On Sight.

Written By

Humans by birth. Gamers by choice. Goomba Stomp is a Canadian web publication that has been independently owned and operated since its inception in 2016.

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