The 50 Greatest Rom-Coms – The Ringer

Mayra StankoApril 21, 2022

15 36 minutes read

Once you discover a theme week you wish to spend the remainder of your life with, you need the remainder of your life to begin as quickly as potential. Fortunately, The Ringer hereby dubs this week Rom-Com Week, a celebration of one of the pleasant, fascinating genres in movie. Head to the highest of the Empire State Constructing, order what she’s having, and be a part of us as we dig into all the pieces the rom-com has needed to supply through the years—starting with, in fact, this rating of the 50 greatest romantic comedies in film historical past.

50. 500 Days of Summer time

Very like its foremost plot machine, the reception of 500 Days of Summer time feels depending on time. Ask somebody how they felt concerning the film in 2009 they usually may name it probably the most authentic rom-com in many years. As of late although, that response may elicit mockery: the fashionable edits and classic clothes go solely thus far in obscuring some extremely questionable character improvement. “For those who took out the gimmick and watched these scenes so as, you’d see it’s a couple of codependent stalker and the empty vessel he latches onto,” a basic Trustworthy Trailer hilariously concludes. However to 500 Days’ credit score, the movie was upfront from the start that it was “not a love story.” The truth is, honesty could also be one of the best trait about this nuanced dramedy: The characters might not deserve sympathy, however for lots of viewers, the story is relatable—whether or not they’re the Tom or Summer time of a relationship. Look no additional than the “Expectations vs. Actuality” scene, a bitter climax that almost all of us would admit to experiencing in some kind. —Aric Jenkins

49. To All of the Boys I’ve Beloved Earlier than

There could also be no higher endorsement for a rom-com than when your entire web falls in love together with your lead in a single day. On this case, that may be Peter Kavinsky (Noah Centineo), an enthralling lacrosse participant who establishes a pretend relationship with shy outcast Laura Jean (Lana Condor) to make his ex jealous earlier than promptly falling for her. Extra refreshing than Centineo’s on-screen charisma, nevertheless, is the best way TATBILB celebrates Laura Jean’s cautious individuality, main her to her very first real-life romantic connection at precisely the tempo she chooses. —Alyssa Bereznak

48. Candy Dwelling Alabama

Candy Dwelling Alabama belongs to the wonderful period between You’ve Obtained Mail and Knocked Up, when rom-com premises have been stretching the boundaries of credulity to remain inside the boundaries of the style earlier than a film got here alongside and made realism de rigueur. Is it utterly ridiculous that this film hinges on a person’s years-long refusal to signal divorce papers? Or that the not-quite-ex-husband (Josh Lucas) is a “lightning glass” mogul? Or that Reese Witherspoon’s Melanie allegedly blew up a cat as a teen and positively outed considered one of her mates as an grownup? Or that Patrick Dempsey’s character is being groomed by his mother (Candice Bergen), the mayor of New York Metropolis, to be the president of america? Sure—clearly all of that’s ridiculous. But it surely’s additionally pleasant, in a approach that solely ridiculous rom-coms might be. —Andrew Gruttadaro

47. Silver Linings Playbook

Jennifer Lawrence and Bradley Cooper have been already stars by the point David O. Russell’s 2012 sleeper hit got here out, however Silver Linings Playbook is what established them as capital-S Severe Actors. Their performances as a younger widow with a foul popularity and a rubbish bag–sporting Eagles fan decided to win his ex-wife again after a stint in a psychological well being facility have been touching, humorous, and critically lauded. After the film landed Oscar nominations in all 4 performing classes, with Lawrence successful for Greatest Actress, Lawrence and Cooper turned Academy Award mainstays. Perhaps they might’ve gotten there anyway, however trying again on the diner scene and the dance competitors, it’s exhausting to disclaim that Silver Linings Playbook catapulted them to new ranges of success. —Julianna Ress

46. Harold and Maude

On the heart of any good romantic comedy is an unlikely couple that is smart as you peel again the layers. And maybe no couple in film historical past appeared as unlikely on the floor because the titular pairing of Harold and Maude. The 1971 movie follows the exploits of Harold Chasen—a morbid 19-year-old vulnerable to faking his personal loss of life and subverting his mom’s needs—who falls for Maude Chardin, a sunny 79-year-old focus camp survivor who loves a superb joyride. Alongside the best way, Harold additionally learns to like life due to her. Seen immediately, you may see its standing as the muse for films like Rushmore and Licorice Pizza. However 50 years in the past, audiences and critics weren’t fairly prepared for such a unusual story: Harold and Maude bombed on the field workplace, and the opinions seemed worse than the receipts. (Selection wrote on the time that the film had the “enjoyable and gaiety of a burning orphanage.”) As time wore on, nevertheless, the movie reached cult standing, recouping its finances years later and retrospectively incomes its deserved reward (significantly for Colin Higgins’s screenplay). It might have appeared unlikely at first, however ultimately, all of it made sense. —Justin Sayles

45. Palm Springs

Film-watchers have been missing for good rom-coms in 2020, which is why it’s comforting that Palm Springs, at its core, makes use of a basic template: girl-meets-boy-who-has-some-growing-up-to-do. In fact, a part of the boy’s downside right here is that he’s caught in “a kind of infinite time-loop conditions you may need heard about,” which makes rising up a little bit additional difficult. Palm Springs was a contemporary take, and Samberg’s style for the absurd is enjoyable to observe within the context of a well-worn style. However finally what makes the film is what makes most good rom-coms: nice dialogue, good chemistry, and having all of it work out ultimately. —Nora Princiotti

44. 10 Issues I Hate About You

It’s so extremely exhausting to make a film about highschool that’s truly cool, however 10 Issues I Hate About You makes it appear simple. The screenplay hails from legendary rom-com writing duo Kirsten Smith and Karen McCullah (with an help from William Shakespeare and his little ditty The Taming of the Shrew) and an iconic Julia Stiles efficiency as Kat Stratford launched a era of teenage viewers to Joan Jett, open hostility towards a patriarchal society, and a comically sized copy of The Bell Jar.

And Heath Ledger as Patrick Verona created the blueprint for a teen rom-com heartthrob. In any case, women don’t like boys—women like rebels with hearts of gold who steal a microphone to sing Frankie Valli throughout soccer apply. In 1999, these characters have been genuinely radical, their jokes legitimately humorous, and 20 years later, it nonetheless holds up. There’s nothing to hate about 10 Issues—not even shut, not even a little bit bit, not even in any respect. —Jodi Walker

43. How you can Lose a Man in 10 Days

If anybody continues to be laboring below the phantasm that plausibility and unpredictability are conditions for watchability within the realm of rom-coms, they need to refresh their reminiscence of How you can Lose a Man in 10 Days. This can be a film through which Matthew McConaughey performs a Staten Island native with a Texas accent, and the Knicks play the Kings within the NBA Finals (one sport of which appears to happen on the identical time and venue as a Celine Dion live performance). Neither of which is much less far-fetched than the central setup, which revolves round two duplicitous seducers who hook up for work-related causes however can’t fairly ditch one another, even after the reality comes out. Can a film be mentioned to have plot holes if its plot as an entire is that this foolish? That’s a rhetorical query. McConaughey and Kate Hudson have chemistry, the film is bubbly and breezy, and no “we met below false pretenses however then legitimately fell in love” story looks like a stretch after this. Once you’re in the precise temper, implausibility and predictability are perks, not issues. —Ben Lindbergh

42. She’s Gotta Have It

Let’s start by stating the plain: The rape scene in She’s Gotta Have It was a large mistake, and one that almost disqualifies the movie because the feminist basic that director Spike Lee envisioned it as. (Lately, Lee has mentioned he regrets the scene, and when he tailored the movie right into a Netflix collection in 2017, he opted to not embody the plot thread.) However regardless of that blight, Lee’s directorial debut stays a landmark of ’80s unbiased cinema and one of the trustworthy portrayals of young-adult romance on this listing. She’s Gotta Have It is the story of Nola, a younger, sexually liberated Brooklynite juggling three lovers. Finally, the three discover out about one another and examine notes—it’s predictably a nightmare, if just for the extremely awkward foursome Thanksgiving dinner that reveals every of Nola’s suitors to be an even bigger bozo than beforehand thought. By the top of the movie, Nola is able to give monogamy a shot. She’s Gotta Have It ends with Nola going to mattress by herself, although. She found an important love of all: self-love. —Sayles

41. She’s the Man

Identify a greater Amanda Bynes efficiency than the one we get in She’s the Man … I’ll wait. I don’t care what Rotten Tomatoes says, it’s a extremely underrated teen rom-com. Bynes delivers in a task the place she’s caught between identities, not girly sufficient to be a debutante but additionally not manly sufficient to be revered by her male friends. Her chemistry with a young-ish Channing Tatum is off the charts, and her exaggerated tackle how women assume guys act is comedic genius (particularly the tampon scene). I’m fairly certain each younger woman flocked to this film again within the day and now, it’s no doubt well worth the rewatch. —Kiera Givens

40. 13 Occurring 30

Each child fantasizes concerning the superior life they’re gonna have after they develop up. 13-year-old Jenna Rink truly will get to see her dream come true, however at a price: She additionally turned out to be a shitty grownup. It’s a enjoyable twist on the Huge template, and Jennifer Garner’s doe-eyed efficiency sells the earnestness of trapped-in-an-adult-body Jenna. And whereas she faces some harsh realities of maturity (like discovering a unadorned man in her bathe), she additionally will get to return to childhood with the information that her dorky however candy greatest buddy grows as much as be Mark Ruffalo. Their charming chemistry is what makes this film a basic rom-com on high of a considerate coming-of-age story. Plus, Judy Greer! The gown! Wait, was that Brie Larson? The “Thriller” dance! 13 Occurring 30 has one thing for all ages. —Ress

39. Knocked Up

A seminal film on reflection, Knocked Up achieved many issues: It established Judd Apatow as a recent king of comedy including onto the success of The 40-Yr-Outdated Virgin; it turned Seth Rogen into a number one man and Katherine Heigl (briefly) into a number one girl; it made us notice simply how unimaginable Paul Rudd truly is. The film even prompted a notorious discourse on sexism that arguably kick-started the dimming of Heigl’s star, a destiny that’s felt more and more problematic with every passing 12 months. Like most comedies from the aughts and earlier than, Knocked Up has its share of points. But it surely’s additionally an endearing lesson on what it means to take duty and what it takes to make a relationship work. Plus, Rudd and Rogen riffing about Robert DeNiro’s sneakers will merely by no means get previous. —Jenkins

38. The Greatest Man

Think about discovering out from a novel that your fiancée cheated on you together with your greatest man. Are you continue to getting married? The Greatest Man could also be the messiest rom-com of all time—the film is chaotic because it follows a close-knit group of Black mates who reunite for a marriage and battle with insecurities, success, and entanglements. Malcolm D. Lee, cousin of Spike, does a unbelievable job directing a bit that explores marriage and infidelity by the eyes of males, whereas Taye Diggs, Terrence Howard, Morris Chestnut, Sanaa Lathan, and Nia Lengthy ship phenomenal performances to make the movie a timeless basic. —Givens

37. The Marriage ceremony Planner

It’s shocking that Jennifer Lopez and Matthew McConaughey have but to group up once more given their on-screen chemistry and the longevity of this movie that hit theaters 21 years in the past. One purpose why The Marriage ceremony Planner holds up many years later may be as a consequence of the truth that it’s dripping in rom-com tropes: There’s the superbly timed meet-cute, the star-crossed lovers side, after which, in fact, Judy Greer taking part in considered one of her career-defining greatest buddy roles. The opposite purpose why this film works so effectively is, in fact, the performances of Lopez and McConaughey. They’re each on the peak of their powers—she a stunning, career-minded girl with a false relatability that reads as charming, he a hunky physician with the right quantity of mischief that beguiles us from the second we hear that slight Southern drawl. All collectively, it’s rom-com magic. —Amelia Wedemeyer

36. The Reducing Edge

Turtlenecks, tequila, and TOE PIIICK: the winners’ podium of our hearts! 1992’s The Reducing Edge paired the coaching montages and monitor fits of a sports activities flick with the disdainful-to-disarmed chemistry of a romantic comedy, tracing the best way snooty Kate Moseley and lunch-pail Doug Dorsey be taught to collaborate on the ice and coexist off of it. (It additionally educated a era of youths about learn how to create a salt lick on their wrists.) Written by Tony Gilroy, who would go on to pen Michael Clayton, Armageddon, and virtually each Bourne film, the script was dropped at life by D.B. Sweeney’s hockey-inflected chirps and Moira Kelly’s haughty sputter. (No different human on Earth can mimic the best way she pronounces “please don’t let me hold you from the trough;” someway, a lot of the film was shot whereas she had a damaged foot.) Sweeney advised Leisure Weekly that within the many years because the film’s launch, “I hear ‘toe choose’ 5 occasions a day.” And truthfully? For a romantic catchphrase on par with “Right here’s you, child” and “You had me at hi there,” that really appears low. —Katie Baker

35. Loopy, Silly, Love

In relation to the scene-stealing chemistry between Ryan Gosling and Emma Stone, La La Land desires what Loopy, Silly, Love has. Loopy, Silly, Love was launched proper in the course of Gosling’s golden period, and he spends the film reminding us what he can do when given a stable comedic, romantic automobile. The Stone-Gosling ‘ship isn’t even the spotlight of the film—you may argue Gosling’s chemistry with Steve Carell’s newly single dad shines even brighter, and in case you haven’t seen a meme from one of many buying scenes, you most likely weren’t on the web from 2011 by 2015. Positive, components of the movie haven’t aged significantly effectively, however largely, the film holds up. If La La Land had tossed in the elevate from Soiled Dancing, perhaps it will have received Greatest Image in any case. —Kate Halliwell

34. Bull Durham

Author-director/former baseball prospect Ron Shelton advised The Ringer in 2018 that Bull Durham is “about two people who find themselves at some extent of their lives the place working into one another is forcing them to face the query they haven’t wished to face. Is it time to cease what I’m doing and take some possibilities?” Crash Davis (Kevin Costner) is a profession minor leaguer who has no shot on the bigs. Annie Savoy (Susan Sarandon) is an English professor who has a romance with a ballplayer each season earlier than shifting on. Naturally, they find yourself collectively.

However first, fireworks. There’s a love triangle between Annie, Crash, and phenom Nuke LaLoosh (Tim Robbins); there’s Crash’s well-known monologue when he says he believes in—amongst different issues—“lengthy, sluggish, deep, delicate moist kisses that final three days;” and there’s a scene when Crash paints Annie’s toenails crimson. There could also be funnier sports activities films on the market–Shelton’s White Males Can’t Bounce, for instance—however none as romantic and attractive as Bull Durham. —Alan Siegel

33. Amélie

I keep in mind the best way I felt after I watched Amélie for the primary time. To not completely lean into the truth that this can be a French movie, however I’m certain that everybody studying will agree that it has a sure je ne sais quoi—from the manic pixie woman title character (her iconic bob with bangs!) to the touring gnome secondary plot (a unusual prank from our eccentric heroine!). The story itself is flirty, whimsical, and in contrast to many romantic comedies these days, it was beloved by critics, incomes 5 Academy Award nominations, together with Greatest International Language Movie and Greatest Authentic Screenplay. —Wedemeyer

32. Loopy Wealthy Asians

For some purpose, I waited longer than most to observe Loopy Wealthy Asians. I refused to purchase into the hype. Now although, I get upset if I don’t handle to observe the film at the very least as soon as a month. Humorous how the tides change! Based mostly on the bestselling novel by Kevin Kwan, Loopy Wealthy Asians delivers on each side of the title. The predominantly Asian and Asian American forged capably showcases the cultural variations between the 2 teams, and it’s simple to only get misplaced within the romance between Nick and Rachel. At this level it’s completely wild to me that we don’t have a sequel but! —Givens

31. The Huge Sick

There are, in each style, tentpole moments; occasions when a film or an individual or an concept lands with such measured gravity and brilliance that you realize, from there going ahead, all the pieces goes to be totally different. With rom-coms, there have been 5 simple tentpole moments. There was Diane Keaton powering Annie Corridor to 4 Oscar wins in 1977. There was Nora Ephron principally wholesale inventing the fashionable rom-com with When Harry Met Sally in 1989. There was Boomerang exhibiting what it will seem like if everybody however white folks weren’t boxed out. There was Julia Roberts placing up untouchable numbers within the ’90s with Fairly Girl, My Greatest Good friend’s Marriage ceremony, Notting Hill, and Runaway Bride. After which there was The Huge Sick revitalizing and modernizing the rom-com once more in 2017. Pushed to brilliance by Kumail Nanjiani, Zoe Kazan, Holly Hunter, and Ray Romano (to not point out Emily V. Gordon, who cowrote the film), it’s a wise, tender, nuanced film that utterly upends the issues audiences had come to count on from rom-coms whereas concurrently serving us precisely what we wanted from the style. —Shea Serrano

30. 27 Clothes

Katherine Heigl, queen of the mediocre rom-com. James Marsden, king of the fellows who by no means get the woman. Smash them collectively and also you get 27 Clothes, an underrated spotlight of each their rollercoaster rom-com careers. For as soon as, Marsden isn’t the forlorn, neglected ex. (For that, confer with The Pocket book, Enchanted, or actually any of his different roles.) Our man locks it down this time, and it’s what he deserves because the charming, cheeky journalist writing a narrative about Heigl’s character, who is kind of actually all the time the bridesmaid, by no means the bride. The film is admittedly uneven, however highlights embody rom-com classics like a bar sing-along scene and an elite outfits montage of the titular 27 clothes. —Halliwell

29. Working Woman

Classifying Working Woman as solely a romantic comedy sort of undersells the film’s significance. From the opening aerial photographs of the Statue of Liberty and administrative assistant Tess McGill’s (Melanie Griffith) commute into Manhattan on the Staten Island Ferry, it’s clear that director Mike Nichols goes to be tackling large themes—the American Dream, sexism within the office, the cruelty of the company ladder, classism. But, as well as to all that, there’s a goosebump-inducing love story between Tess and Harrison Ford’s Jack Coach. The 2 group up and fall in love. Their remaining scene collectively could also be one of the iconic in rom-com historical past; they eat breakfast as Tess will get prepared to go off to the primary day of her new job. Earlier than she leaves, Jack sends her off with a brand-new monogrammed lunchbox, full with a peanut butter and jelly sandwich. It’s one of the best reward a companion can provide. —Siegel

28. There’s One thing About Mary

Initially: I feel if Inexperienced E book by no means comes out, then this film is sitting comfortably within the high 20 on this listing. Peter Farrelly ought to’ve been glad with hair gel that isn’t truly hair gel being his legacy.

There’s One thing About Mary was a revelation—a deliriously R-rated rom-com that made $370 million worldwide on a $23 million finances, launched Ben Stiller and Cameron Diaz into the stratosphere, and have become the one movie to ever envision what it’d seem like if a person acquired his frank and beans caught in a zipper. This film broke actual floor by including debauchery and insanity to a historically buttoned-up style, a stroke of genius topped solely by casting peak ’90s Brett Favre as Mary’s longtime ex-boyfriend. —Gruttadaro

27. Can’t Purchase Me Love

Can’t Purchase Me Love belongs to a gaggle of of-their-time rom-com classics with films like Secret Admirer and Simply One of many Guys—these ’80s movies with the form of premises and scripts which may elicit that well-known response of “They may by no means make this immediately.” However of these films, Can’t Purchase Me Love stands on the high. Starring an extremely younger Patrick Dempsey and a quintessential ’80s teen film love curiosity in Amanda Peterson, it’s a pioneering play on the “Give Geeks a Likelihood” trope: Ronald is a dork who loves costly telescopes however goals of being cool; Cindy is the favored woman who throws bangers and spills wine on her mother’s suede. Their relationship begins as a enterprise transaction and culminates with the belief that it’s a lot greater than that, with so much of juvenile drama in between. Put it this fashion: The film’s so good that Nick Cannon and Christina Milian had no selection however to remake it for the 2000s crowd. —Gruttadaro

26. Boomerang

You could have Eddie Murphy, one of many funniest and most charming folks to have ever walked throughout a Hollywood stage, taking part in an unstoppably suave bachelor intent on sexing his approach towards discovering what he deems to be an ideal girl. You could have Robin Givens reverse him, taking part in mentioned “good girl,” who, moderately than falling for any of Murphy’s tips and ways, twists him up right into a knot time and again. You could have David Alan Grier and Martin Lawrence taking part in Eddie’s mates, neither of whom has any actual concept how precisely to course of what precisely it’s that makes girls fall for Eddie however each of whom strategy the conundrum in hilarious methods. You could have Halle Berry because the sudden “common girl” (lol) Eddie ultimately finally ends up with. You could have John Witherspoon giving perhaps the best ever walk-off house run scene in rom-com historical past. And you’ve got Grace Jones, Eartha Kitt, Tisha Campbell, a younger Chris Rock, and Geoffrey Holder chucking joke grenades into each scene they’re in. And nonetheless, regardless of being arguably the funniest assortment of individuals ever assembled in a rom-com, Boomerang is ready to squeeze the emotion out of you each time it decides to try this. —Serrano

25. Say Something

Say Something doesn’t stay by growth field alone. Sure, its signature picture is among the many most recognizable film moments ever, encapsulating the idea of rom-coms in a single body. However Cameron Crowe’s directorial debut is way more than that indelible scene. Lloyd Dobler is the patron saint of people that take time to resolve on a path in life, and his unlikely however credible bond with Diane Courtroom captures the dream of with the ability to “exit with somebody you wouldn’t even must exit with.” The movie unfailingly respects its characters and its viewers; as Roger Ebert wrote, “That such intelligence might be contained in a film that’s concurrently so humorous and so entertaining is a few sort of a miracle.” I’m not usually a proponent of reboots or decades-distant sequels, however I’m wondering what Lloyd and Diane are so far. It’s most likely higher to go away their love previously than to be taught that Diane didn’t experience the Reid fellowship to fame and fortune and Lloyd ended up shopping for or promoting one thing processed in any case. But it surely’s a testomony to the OTP of ’80s teen films that neither I nor Crowe can stop them.—Lindbergh

24. Love Really

Love Really is many issues to many individuals: rom-com, Christmas film, ensemble forged manufacturing, Liam Neeson-biting-off-an-awful-lot-to-help-his-kid style movie. To some, it’s a problematic mess through which unresolved plot particulars and unhealthy conduct (infidelity, flirting with subordinates, touring to Milwaukee) paints a shallow image of affection whereas celebrating the nebulous connection between romance and the vacations. And but, to me, it’s good, or at the very least endlessly charming in its tacky portrayal of affection in lots of kinds. —Princiotti

23. Moonstruck

There’s no metropolis extra romantic than New York (sorry, Paris), and there’s no New York film extra romantic than Moonstruck (sorry, Manhattan). Nicolas Cage—simply 23 on the time—would go on to make a profession out of his irrepressible eccentricity, however in Moonstruck, each single actor is vibrating on his gloriously bizarre frequency, giving indelible, odd life to John Patrick Shanley’s Oscar-winning screenplay. As Brooklyn widow Loretta Castorini, Cher matches Cage beat for beat in his portrayal of maimed baker Ronny Cammareri, the estranged youthful brother of her sad-sack fiancé Johnny. In Shanley’s indelible phrases, she’s a bride and not using a head; he’s a wolf and not using a foot. As soon as he flips a desk out of rage and lust, it’s throughout for them.

This can be a story the place the 2 lovers’ first date takes place on the Metropolitan Opera, the place they watch the ravenous artists of La Bohéme succumb to tuberculosis. In a world the place the chilly, exhausting floor awaits us all, what selection do we have now however to like who we will and maintain household shut? As Ronny says, we’re right here to destroy ourselves and break our hearts and love the incorrect folks and die. Would possibly as effectively get on with it. —Alison Herman

22. My Huge Fats Greek Marriage ceremony

Earlier than it will develop into the highest-grossing romantic comedy of all time, My Huge Fats Greek Marriage ceremony started as a one-woman play by Nia Vardalos that was broadly primarily based on her personal private life and her large, rowdy household. The story of the way it acquired from A to B concerned Rita Wilson and Tom Hanks—and likewise Vardalos’s insistence that studios retain the acute specifics of her imaginative and prescient. The result’s a 2002 movie that’s goofy but exact, a rom-com brimming with vim and a LOT of fam. (Vardalos wrote on Reddit that her personal dad used Windex on a wart, that “the lady is the neck” is one thing her mom mentioned, and that Toula isn’t simply the lead character within the film—it’s her cousin’s identify.) A feast of bundt cake and lamb, frosted-cupcake wedding ceremony clothes and lunch bag moussaka, My Huge Fats Greek Marriage ceremony is a film with a satisfying conclusion: that it’s all Greek to everybody, and that actually, we’re all simply fruit. —Baker

21. The 40-Yr-Outdated Virgin

Not all the pieces Judd Apatow touches nowadays turns to gold—see The Bubble or that tweet about how Will Smith’s slap might’ve killed Chris Rock—however it’s important to hand it to the person for, amongst many different accomplishments, someway perceiving whereas producing Anchorman that the individual taking part in Brick Tamland was able to being a romantic lead. Apatow and Steve Carell cowrote this film primarily based on considered one of Carell’s recurring improv sketches; crucially, their script and Carell’s tender portrayal (coupled with the dedication to do his personal stunt within the chest-wax scene) made Andy a sympathetic protagonist whose plight was relatable, moderately than the pitiful butt of each joke. Whether or not or not you assume The 40-Yr-Outdated Virgin is without doubt one of the greatest rom-coms ever, you could admit it was one of the influential. The film made a star out of everybody related to it who wasn’t one already, and it established a profitable lane for a lot of bro-y-but-still-sensitive rom-coms to return. —Lindbergh

20. Excessive Constancy

The highest 5 issues which can be nice about Excessive Constancy:

5. Nick Hornby, creator of the guide that impressed the movie, basically laid the groundwork for 70 p.c of digital media. Say what you need, however lists are entertaining and helpful.

4. It goes with out saying, however the soundtrack of this film is, because the protagonist Rob would say, “an all-timer.” The Velvet Underground. The Kinks. Elvis Costello. Stevie Surprise. A set of artists genuinely worthy of musical snobbery.

3. That is the movie that launched mainstream audiences to Jack Black, and with out Jack Black, we might have by no means seen College of Rock.

2. Talking of the forged, we will’t slight John Cusack right here. Say Something is one other rom-com basic, however Excessive Constancy is arguably Cusack’s best work in any style. An ideal steadiness of humorous pretension and relatable vulnerability; it’s exhausting to think about one other actor embodying this function so effectively.

1. Excessive Constancy wasn’t afraid to get darkish; it ranked breakups and songs about loss of life, and it took care to acknowledge its central relationship was made up of two deeply flawed folks. This film won’t be the primary that involves thoughts while you consider “romantic comedy,” however Excessive Constancy is without doubt one of the most genuine depictions of a relationship you’ll see on movie. —Jenkins

19. The Princess Bride

I don’t all the time agree with Aaron Rodgers, however I can nonetheless recall when he named The Princess Bride as his favourite movie, selecting it over films you’d assume a soccer participant would listing like The Darkish Knight. However what was nice about Rodgers’s seemingly subversive selection was that it actually wasn’t all that stunning. The Princess Bride defies our expectations of each fantasy and romance with its use of comedy and inventive storytelling, masterfully tied collectively by screenwriter William Goldman. As soon as extra, we root for all of the memorable characters, from our foremost love pursuits Princess Buttercup and Westley to the beloved sidekicks Inigo Montoya and Fezzik and the unnamed grandfather and grandson who assist facilitate the story. It’s a basic rom-com—even soccer gamers understand it. —Wedemeyer

18. Bridget Jones’s Diary

Loads of entries on this listing are variations of age-old tales within the public area, from Shakespeare’s comedies to Austen’s social farce. However Bridget Jones’s Diary is a sort of twin translation—not simply of Delight & Prejudice, although Colin Firth does present a visible hyperlink in his second flip as (a model of) Mr. Darcy. It’s additionally primarily based on Helen Fielding’s hit novel of the identical identify, the high-water mark of the so-called “chick lit” wave. Renée Zellweger might do a surprisingly good British accent for an American star, however it’s Fielding who deserves credit score for filtering Elizabeth Bennet’s headstrong heroine by a extra trendy set of neuroses like ingesting, weight achieve, and trendy careerism. Consequently, Bridget Jones’s Diary is a contradictory mixture of timeless themes and particulars that mark it as a relic of, or maybe a enjoyable throwback to, the early aughts. Anybody can relate to Bridget’s battle to decide on between Mr. Proper and Mr. Flawed, particularly when her Mr. Flawed is performed by Hugh “Gosh” Grant; her use of Spanx within the getting-ready montage, however, is a little more particular to its second. Bridget Jones is everlasting, but additionally a time capsule—a reasonably neat encapsulation of the romantic comedy itself. —Herman

17. Two Weeks Discover

Hugh Grant portrays the egocentric and helpless actual property billionaire George Wade; Sandra Bullock is Lucy Kelson, an environmental lawyer who agrees to work for George’s agency solely after she realizes she will save considered one of her beloved neighborhood facilities. Lucy grows pissed off together with her boss’s child conduct, however after she decides to resign, George and Lucy spend her remaining two weeks at work falling for one another. What makes this film memorable is Bullock’s steadfast dedication to bodily comedy. Not solely does she hug a wrecking ball (you’re welcome for the inspiration, Miley), her head is savagely hit by a tennis ball, and she slides in the course of a moist freeway on her strategy to relieve herself after consuming too many chili canines. Being that this was one of many first productions to happen in New York Metropolis after 9/11, this movie additionally serves as one more love letter to the Huge Apple. Sure, I do know When Harry Met Sally options Katz’s Deli and the Met, however Two Weeks Discover has Norah Jones, Mike Piazza, and Donald Trump as supporting characters. This film additionally had us all working to LimeWire to tear Counting Crows and Vanessa Carlton’s model of “Huge Yellow Taxi.” If that isn’t an endorsement, I don’t know what’s. —Bridget Geerlings

16. The Vacation

One time I used to be venting a couple of man to my buddy, and after listening politely for a couple of minutes, she minimize in to say “Watch The Vacation,” like she was a physician writing a prescription. Reader, I quickly understood why. The 2006 movie facilities round two girls who’re romantic opposites: Iris (Kate Winslet), who’s spent years in Surrey, England, pining for an unavailable ex, and Amanda (Cameron Diaz) who drives away her companion by burying herself in her L.A.-based movie-marketing enterprise. The 2 of them meet on a house-swap web site and conform to commerce lives for the vacations—a transfer that permits for gratuitous actual property montages and, most crucially, alternatives to search out love the place they’d least count on it. These adventures add as much as a hopeful tackle heartbreak: that past every dead-end relationship is a world of chance for what comes subsequent. It’s a message so soothingly executed by Nancy Meyers that it actually does kinda really feel like medication. —Bereznak

15. Hitch

A movie with prime Will Smith, Kevin James, and Eva Mendes; a enjoyable and interesting story; and a baller soundtrack? Not solely is Hitch one of the underrated rom-coms of all time, I’m a agency believer that it’s Will Smith’s greatest efficiency as an actor, PERIOD. He’s good in Ali, certain; Oscar-worthy in King Richard; he doesn’t get sufficient love for his voice work in Shark Story. However let’s actually speak about it! This scene proper right here IS cinema. “They don’t want no pizza, they acquired meals there” as James does his “white boy on the disco” bit is without doubt one of the funniest moments in rom-com historical past. It’s time to lastly give Hitch it’s simply due.

Subsequent topic. —Jomi Adeniran

14. 4 Weddings and a Funeral

4 Weddings and a Funeral isn’t a terrific comedy as a result of it’s peppered with comedians ripping off one gag after one other. (You understand who places me in a temper to chortle? Kristin Scott Thomas.) It’s a terrific comedy as a result of it explores the enjoyment of friendship; while you’re with your mates, the laughs simply come naturally—however a terrific group of mates will get you solely thus far, as Hugh Grant’s Charlie discovers when he falls for an elusive American who retains popping up in his life. Although the movie bounces from one farce to a different over the course of its 4 weddings, the most memorable scene is the funeral, through which John Hannah’s Matthew recites W.H. Auden’s “Funeral Blues” on the memorial service for his just lately deceased companion. It’s dramatic reduction, so to talk, a solemn reminder that love and friendship are about tears in addition to laughter. —Michael Baumann

13. Groundhog Day

If Invoice Murray’s authentic hopes for Groundhog Day received out, the movie might not have made this listing: “It was an interpretation of the parable about how all of us repeat our lives as a result of we’re afraid of change,” he mentioned of his preliminary ideas on the unique script. “I assumed it might simply be the funniest factor ever.” However director Harold Ramis had a special imaginative and prescient: “the concept real love can prevent from a lifetime of monotony,” Murray mentioned. So whereas on the floor, the granddaddy of time-loop films doesn’t seem like a pure rom-com—the romance factor doesn’t develop into an element till the movie’s second half—it expresses a sentiment core to human nature. Murray performs the coarse Phil Connors, who finds himself repeating the identical day time and again. After studying to stay inside the surreality of the scenario, he begins to deal with self-improvement: skating, ice sculpting, studying French, simply turning into an honest human general. Finally, it helps him get the woman and in flip, escape the hell he’d been dwelling by (for presumably so long as 34 years). Loads of rom-coms have targeted on the insufficient man having to develop to search out the love he wants. Few have made it an existential query to the diploma Groundhog Day did. —Sayles

12. Whereas You Had been Sleeping

Lucy (Sandra Bullock) is a transit employee who counts tokens (not the non-fungible ones) for Chicago subway riders. All she desires in life is to be seen and to get at the very least one stamp on her rattling passport. She additionally has an unrequited crush on Sandy Cohen—I imply, Peter Callaghan, who’s performed by Peter Gallagher. Peter is an prosperous commuter who virtually will get run over by the precise subway earlier than Lucy spots him and saves his life. Whereas escorting him to the hospital, she is mistaken for his fiancée and fails to right this misinformation as Peter’s household rushes to his bedside as he suffers from a coma. Lucy, who would in any other case be house alone for the vacations, is swept away by the kindness bestowed on her by Peter’s household. After agreeing to spend Christmas with them, she meets Peter’s brother Jack (denim advocate Invoice Pullman). As Peter and his iconic eyebrows relaxation away on a hospital mattress, Lucy shockingly begins to fall for Jack. Come for Pullman and Bullock, which is electrical sufficient to energy all the movie’s Christmas bushes, and keep for Michael Rispoli workshopping a personality for The Sopranos. Extra importantly, I really feel compelled so as to add that that is Daniel Radcliffe’s favourite Sandra Bullock movie. —Geerlings

11. One thing’s Gotta Give

The one factor higher than a Nancy Meyers kitchen is a Nancy Meyers kitchen within the Hamptons inhabited by Diane Keaton and Jack Nicholson making pancakes, simply getting ready to realizing they’re falling in love. There’s one thing about including love pursuits of their golden years to the “enemies to lovers” trope that simply makes it hit totally different. Erica and Harry are sharp, conscious, and faster to comprehend their attraction to 1 one other as a result of they’ve each already lived wealthy, full lives. I imply, we’re already chopping off turtlenecks earlier than the film is midway finished! Plus, One thing’s Gotta Give is filled with whopper traces: “Phrases have been invented to explain girls such as you,” and, “You are a girl to like.” And but at the same time as Harry says this stuff—and actually goes to the hospital on three separate events in direct response to Erica—he struggles to comprehend that Erica has already modified the trajectory of the remainder of his life. However after a beard and a little bit repentance to the younger girls of Manhattan, he will get there. And simply as each rom-com ought to, all of it ends in Paris, sealed with a kiss. —Walker

10. Forgetting Sarah Marshall

Forgetting Sarah Marshall ought to’ve aged poorly, contemplating the plot is a form of Backyard State-by-way-of-sophomoric Apatovian silliness. But it surely didn’t, as a result of it’s one of many funniest films ever made. There are comedies—good comedies, humorous comedies—whose greatest joke isn’t as side-splittingly hilarious as Paul Rudd’s deadpan supply of, “Oh yeah, you’re that man who works with Kaiser Permanente.”

It’s the sort of film that’s humorous on repeat viewing particularly as a result of there are jokes you missed the primary time by since you have been laughing so exhausting. There’s no wasted effort from its loaded forged, from Jonah Hill to Mila Kunis to Russell Model, at that magical second in time when just one facet of the Atlantic was sick of Russell Model. And amid all of the R-rated comedy is a surprisingly endearing hero: a cuddly, self-loathing, piano-playing large performed by Jason Segel. To alter or take away one joke, one bizarre facet character, can be to decrease this masterpiece. —Baumann

9. The Marriage ceremony Singer

Adam Sandler has made quite a lot of rom-coms. A few of them are unhealthy. Some are advantageous. Some are simply apparent excuses for, like, a free journey to Hawaii. However The Marriage ceremony Singer is none of those—The Marriage ceremony Singer is good. It’s affected person zero for Sandler and Drew Barrymore’s chemistry, which is so simple that they’ve run it again a number of occasions within the years since. It’s top-of-the-line collections of ’80s music ever assembled, with contributions from David Bowie, the Smiths, the Psychedelic Furs, Spandau Ballet, the Treatment, Thompson Twins, and so many extra. And most significantly, it’s, line for line, one of many funniest rom-coms ever made—from Sandler’s unhappy wedding ceremony singer efficiency to Steve Buscemi’s greatest man speech to Jon Lovitz’s “and I’m reaping all the advantages” line studying to this interplay, which I take into consideration at the very least as soon as every week. It’s a film you may watch 1,000 occasions and nonetheless wanna watch in full when it’s taking part in on TBS—I do know as a result of I’m at the moment describing my standard Saturday evening. —Gruttadaro

8. My Greatest Good friend’s Marriage ceremony

It’s a easy recipe. First you are taking the best rom-com star to have ever lived (Julia Roberts). Then you definately add in one of many all-time-great plot setups (a girl’s greatest buddy is getting married, which nudges her towards the conclusion that her greatest buddy ought to be getting married to her as a substitute). Then you definately add two spotlight-bright performances from folks the digital camera can’t get sufficient of (Cameron Diaz and Rupert Everett). Then you definately add a good-looking and clueless man whose solely job is to be good-looking and clueless (Dermot Mulroney). Then you definately add a scene that every one however calls for you scream “JUST TELL HIM THAT YOU LOVE HIM RIGHT NOW BEFORE IT’S TOO LATE!” (the half when Julia Roberts and Dermot Mulroney are on the boat collectively). After which, lastly, a little bit sprinkle of magic (the half when Rupert Everett is making up a narrative about how his faux relationship with Julia Roberts began and finally ends up with breaking out into track at a lunch). And that’s the way you get top-of-the-line, most enjoyable, smartest, most pleasant rom-coms to have ever been put to movie. —Serrano

7. Sleepless in Seattle

Sleepless in Seattle’s genius is distilled in considered one of its easiest scenes: A bathrobe-clad Annie Reed (Meg Ryan) settles into her pink kitchen, utilizing a knife to take away the pores and skin from an apple in a single steady band as she listens to speak radio. The digital camera closes in on her face because the voice of widower Sam Baldwin (Tom Hanks) describes the magic of assembly his late spouse, and he or she begins to weep. In Annie’s face is a deep longing, the restlessness of somebody who desires greater than Mr. Completely Tremendous however feels completely ridiculous for it. In the meantime, 2,764 miles throughout the nation, Sam comforts his son by providing a single element to recollect his mother by: “She might peel an apple in a single lengthy curly strip,” he tells him. “The entire apple.”

Little coincidental glimmers like these tether Annie and Sam for many of Nora Ephron’s good 1993 rom-com, as the 2 of them stay out their very own fairly OK relationships whereas eager for that fabled and elusive spark. It’s solely within the eleventh hour, after many airplane rides and a number of other leaps of religion, that they discover it in one another atop the Empire State Constructing. Witty banter, a stacked forged, and dreamy surroundings apart, that is a kind of uncommon, hopeful tales that makes heroes out of romantics, suggesting no impediment is simply too nice for even the slimmest probability at the actual factor. —Bereznak

6. Notting Hill

Julia Roberts could also be our best meta film star. Even earlier than the Ocean’s Twelve stunt, she was a lady, standing in entrance of a boy, asking him to like her—besides that woman occurred to be an actress named Anna Scott, with a degree of fame not not like Roberts’s almost a decade previous her breakout in Fairly Girl. Roberts is a superb actor, however she’s an excellent higher film star. Notting Hill could also be her best star efficiency, as a result of she doesn’t must attempt to faux she’s an bizarre citizen.

She’s additionally given an ideal scene companion in Hugh Grant, who’s pulling off the alternative trick. Notting Hill leaves Roberts free to embrace her pure charisma; as stammering bookstore proprietor William, Grant perfects the underdog persona that someway makes you neglect you’re watching one of the good-looking and charming people alive. Notting Hill is an ideal snapshot of two performers on the high of their respective video games, assisted by screenwriter Richard Curtis on a legendary run of quotable scripts. Earlier than Rose Matafeo’s pleasant Starstruck got here alongside, Notting Hill set the bar. —Herman

5. Jerry Maguire

By the late ’90s, incessant quoting of Jerry Maguire’s most memorable traces—e.g., “Present me the cash!,” “You full me,” and “You had me at hi there”—turned writer-director Cameron Crowe’s movie right into a corny joke. However make no mistake: It’s top-of-the-line rom-coms of the last decade. Over the course of two hours, the titular rogue sports activities agent shakes his maniacal workaholism and turns into susceptible. Tom Cruise, who was nominated for an Academy Award for his efficiency, manages to make the transformation plausible. However he couldn’t have finished it with out Renée Zellweger, who performs his solely worker/single mother Dorothy Boyd with infinite sweetness. Zellweger deserved an Oscar nomination, too. She acquired robbed. —Siegel

4. Clueless

Two permits don’t equal a license, however impressed casting, among the greatest one-liners in cinematic historical past, and a boatload of yellow plaid equals a genre-defining ‘90s teen film. Amy Heckerling’s adaptation of Jane Austen’s Emma through Beverly Hills is extra com than rom, however its climax takes place when the ditzy however deep Cher Horowitz realizes that she is “completely butt loopy in love with Josh,” her ex-step-brother, performed by a younger Paul Rudd. Earlier than this second, Cher and Josh argue always over her outward frivolity, but she always will get the higher of him verbally. “If I ever noticed you do one factor that wasn’t 90 p.c egocentric, I’d die of shock,” he tells her at one level, to which Cher responds, “Oh, that’d be purpose sufficient for me.” That is the enjoyment of Clueless—it mocks what it loves and it loves what it mocks. Additionally, there’s by no means been a greater on-screen diss than “You’re a virgin who can’t drive.” —Princiotti

3. You’ve Obtained Mail

The third movie that includes beloved actors Meg Ryan and Tom Hanks collectively, and the second that additionally concerned the late director Nora Ephron, You’ve Obtained Mail is without delay a well-worn rom-com story line and a mission that would actually solely have been launched in 1998. Within the film, Ryan performs Kathleen Kelly, the proprietor of a youngsters’s bookstore known as The Store Across the Nook—considered one of a number of references to a 1940 Jimmy Stewart movie with the same plot through which IRL enemies develop into enamored pen buddies with out realizing. However in You’ve Obtained Mail, that plot is given an improve for the occasions involving an over-30 chat room on dial-up AOL; a cutthroat guide superstore paying homage to late-’90s rising behemoths like Borders or Barnes & Noble; and characters who don’t but carry cellphones and as a substitute write overwrought emails about bouquets of freshly sharpened pencils that recipients are legitimately exhilarated to obtain.

In a Self-importance Truthful oral historical past, supporting actor Heather Burns admitted that the movie’s premise had sort of nagged at her a little bit: “I used to be younger and actually idealistic, and I acquired a little bit mad that she finally ends up with the man who’s placing her out of enterprise,” Burns mentioned. (Additionally, Joe Fox? Form of a dick!) However Ephron noticed it in another way. “Heather, the older you get,” she advised her, “you’re gonna notice that issues change and there’s not very a lot that you are able to do about it. And the town adjustments, and that’s simply the best way it’s.” As of late You’ve Obtained Mail isn’t simply dated, it’s virtually out of date: these large unhealthy mega-booksellers of the world have been all however eradicated by the larger, badder Amazon; the New York Observer that Greg Kinnear’s character wrote for was destroyed by Jared Kushner. And but that spark between Hanks and Ryan? As dependable and invigorating as these wonderful adjustments of season in New York Metropolis, irrespective of what number of occasions they arrive again round. —Baker

2. Fairly Girl

With out Julia Roberts, Fairly Girl isn’t second on this listing. With out Julia Roberts, Fairly Girl most likely isn’t even on this listing. The premise of Fairly Girl is sticky, and there’s much more messiness to the vanity, to the plot, to the Jason Alexander of all of it to cope with than your common meet-cute. The romance, and particularly the comedy of this film, lives and dies on the charisma of its heroine. And in 1990, nobody was extra charismatic than a fresh-out-of-the-gate Roberts singing Prince within the bathtub. Positive, some of us had found her in Mystic Pizza, however for many, Roberts was a revelation in Fairly Girl. That’s to not discredit Richard Gere, who excels right here at being as steely as he’s good-looking, but when we have been rating iconic rom-com moments, Julia Roberts cackling at having a necklace field snapped on her fingers needs to be quantity two, second solely to… effectively, no spoilers for the remainder of this rating. Fairly Girl modified the rom-com sport for effectively over a decade, and its legacy continues to reverberate all through artwork and tradition. Fairly Girl-ing has develop into a verb, a complete trope in its personal proper, and the inspiration for an annual date on The Bachelor. It’s virtually an eponym for your entire style. You on the lookout for a rom-com, sugar? You bought one. —Walker

1. When Harry Met Sally

When Harry Met Sally is the best rom-com ever made. It’s the product of the galacticos of the lovable, talky, grownup comedy: Nora Ephron, Rob Reiner, Meg Ryan, Billy Crystal, and Carrie Fisher, all on the peak of their powers. It’s set within the good place and on the good time: a bourgeois nook of New York Metropolis within the Eighties, when males wore sweaters and girls wore hats. You couldn’t ask for higher constructing blocks.

However that’s not what makes it nice. A majority of romantic comedies set their deal with the start of a relationship: the thrilling half. The thesis of When Harry Met Sally is that love shouldn’t be concerning the spark, however about how you’re feeling years down the road. And someway, over the course of simply 95 minutes, we get to see a relationship develop over the course of 12 years. Even contemplating that there are principally solely 4 characters within the film, it’s an astonishing little bit of writing and performing to ascertain two leads who simply get one another so utterly. It’s the rom-com each filmmaker ought to aspire to make, and the romance each couple ought to aspire to have. —Baumann