50 romantic comedies everyone should see in their lifetime

·23 min read
romantic comedies to watch
The are some romantic comedies you should watch at least once. Columbia Pictures/Netflix/Amazon Studios Lionsgate
  • Insider rounded up a list of must-watch romantic comedies.

  • You should add classics like "When Harry Met Sally" and "13 Going on 30" to your watch list.

  • Newer films like "Crazy Rich Asians" and "The Big Sick" offer nuanced takes on modern relationships.

  • Visit Insider's homepage for more stories.

When done right, movies that mix love and laughter can lead to surefire hits.

Here are 50 romantic comedies that everyone should see in their lifetime:

Modern romantic comedies owe a lot to "When Harry Met Sally" (1989).

when harry met sally
Meg Ryan and Billy Crystal in "When Harry Met Sally." Columbia Pictures

Synopsis: Years after a post-college road trip, Harry (Billy Crystal) and Sally (Meg Ryan) reunite in New York City as they ask themselves an age-old question: can a man and a woman be just friends?

Why it's so good: From proclamations of love on New Year's Eve to the endlessly quotable diner scene, "When Harry Met Sally" has remained a classic due to Nora Ephron's unparalleled writing.

Rachel McAdams and Domhnall Gleeson shine in "About Time" (2013).

About Time
Rachel McAdams and Domhnall Gleeson in "About Time." Working Title Films

Synopsis: After he turns 21, Tim (Gleeson) discovers that he can travel through time and learns to make his life better in small ways as he falls in love with Mary (McAdams).

Why it's so good: Gleeson and McAdams' natural chemistry is easy to root for, and "About Time" embraces its sentimentality with a ferocity that's truly endearing.

A couple looks for a place to call home in "Away We Go" (2009).

away we go
John Krasinski and Maya Rudolph in "Away We Go." Focus Features

Synopsis: After his parents unexpectedly move to Belgium, Burt (John Krasinski) and his girlfriend Verona (Maya Rudolph) search the country for a new place to settle down before their baby is born.

Why it's so good: Anchored by compelling performances from Krasinski and Rudolph, "Away We Go" takes its central couple to unexpected places as they define what family means to them.

"Imagine Me and You" (2005) is a can't-miss comedic drama.

imagine me and you
Piper Perabo in "Imagine Me and You." United International Pictures

Synopsis: While preparing for her wedding day, bride-to-be Rachel (Piper Perabo) develops unexpected feelings for her florist Luce (Lena Headey) and questions her attraction to her fiancé (Matthew Goode).

Why it's so good: "Imagine Me and You" is an original romance film that is made all the better by Perabo and Headey's undeniable magnetism.

"She's Gotta Have It" (1986) pairs Spike Lee's vision with a game cast.

She's Gotta Have It Island Pictures
Spike Lee directed and starred in "She's Gotta Have It." Island Pictures

Synopsis: When she can't decide who to be with, Nola Darling (Tracy Camilla Johns) dates three men at once: geeky Mars (Lee), overprotective Jamie (Tommy Redmond Hicks), and wealthy Greer (John Canada Terrell).

Why it's so good: An early entry in Lee's directorial career, "She's Gotta Have It" shows off his signature filmmaking style with the help of a magnetic lead actress and cleverly crafted dialogue.

Stellar acting and writing is abound in "Broadcast News" (1987).

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Holly Hunter in "Broadcast News." Netflix

Synopsis: Hardworking producer Jane Craig (Holly Hunter) creates tension in the newsroom when she finds herself caught between sharp-minded Aaron Altman (Albert Brooks) and handsome reporter Tom Grunick (William Hurt).

Why it's so good: A discourse on the ethics of journalism as well as an ode to love, "Broadcast News" has stood the test of time due to its top-notch cast, intelligent banter, and sensitive direction from James L. Brooks.

"Silver Linings Playbook" (2012) artfully handles multiple themes at once.

Silver Linings Playbook
Jennifer Lawrence and Bradley Cooper in "Silver Linings Playbook." The Weinstein Company

Synopsis: Trying to reconnect with his ex-wife, Pat Solitano (Bradley Cooper) finds a surprising amount of solace in his neighbor, Tiffany (Jennifer Lawrence,) as they both navigate the nuances of mental health.

Why it's so good: With Robert De Niro, Jacki Weaver, and Chris Tucker in supporting roles, "Silver Linings Playbook" benefits from an all-star cast and a story that handles its themes of love, loss, and mental health with aplomb.

"13 Going on 30" (2004) is the silly, good-hearted comedy we need from time to time.

13 going on 30
Jennifer Garner in "13 Going on 30." Columbia Pictures

Synopsis: On her 13th birthday, Jenna Rink (Christa B. Allen) wishes she was "30, flirty, and thriving" and magically wakes up in the body of her future self (Jennifer Garner).

Why it's so good: The film's likability will bank on how much you enjoy magical realism and big dance sequences, but its fun-loving nature will hopefully have you wishing Matty (Mark Ruffalo) was your soul mate, too.

Julia Louis-Dreyfus falls for James Gandolfini in "Enough Said" (2013).

Enough Said
James Gandolfini and Julia Louis-Dreyfus in "Enough Said." Fox Searchlight Pictures

Synopsis: Single mother Eva (Louis-Dreyfus) starts a sweet romance with Albert (Gandolfini), only to realize that he is the ex-husband of her new friend, Marianne (Catherine Keener).

Why it's so good: Released shortly after Gandolfini died of a heart attack in 2013, "Enough Said" is a gentle, witty romantic comedy in its own right, as well as a testament to "The Sopranos" star's softer side.

A compelling protagonist makes "Boy Meets Girl" (2014) a must-see.

Boy Meets Girl
Michael Welch and Michelle Hendley in "Boy Meets Girl." Wolfe Video

Synopsis: After growing up in a small Southern town with her best friend Robby (Michael Welch), 21-year-old Ricky (Michelle Hendley) sets her sights on becoming a designer in New York.

Why it's so good: Using romantic-comedy tropes to its advantage, "Boy Meets Girl" expertly rises above genre expectations while combating transphobia and homophobia.

"10 Things I Hate About You" (1999) redefined rom-coms in the 1990s.

10 things I hate about you
Julia Stiles and Heath Ledger in "10 Things I Hate About You." Buena Vista Pictures

Synopsis: High schooler Cameron (Joseph Gordon-Levitt) plays matchmaker between Kat (Julia Stiles) and Patrick (Heath Ledger) in a roundabout ploy to date her younger sister (Larisa Oleynik).

Why it's so good: Loosely inspired by William Shakespeare's "The Taming of the Shrew," this film redefined high-school rom-coms in the 1990s and propelled Stiles and Ledger into the spotlight.

"Crazy Rich Asians" (2018) hides intricate commentaries beneath a beautiful surface.

Crazy Rich Asians
Constance Wu and Henry Golding in "Crazy Rich Asians." Warner Bros.

Synopsis: Economics professor Rachel Chu (Constance Wu) accompanies her boyfriend (Henry Golding) to a wedding in Singapore and soon discovers that his family is exorbitantly wealthy.

Why it's so good: "Crazy Rich Asians," based on the novel by Kevin Kwan, boasts mind-blowing sets and high-end fashion, but you'll want to stay for the complex narratives on racism, class differences, and cultural expectations.

"Defending Your Life" (1991) is an inspirational romantic comedy.

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Meryl Streep and Albert Brooks in "Defending Your Life." Warner Bros.

Synopsis: After dying on his 39th birthday and waking up in purgatory, Daniel Miller (Brooks) falls for Julia (Meryl Streep) as they await judgment in the afterlife.

Why it's so good: Whimsical and warm, "Defending Your Life" is one of the more inventive films in the romantic-comedy genre that offers a few life lessons along the way.

"The Big Sick" (2017) is inspired by a real-life romance.

The Big Sick
Kumail Nanjiani and Zoe Kazan in "The Big Sick." Amazon

Synopsis: Social pressure from his Pakistani family makes Kumail (Kumail Nanjiani) question the future with his girlfriend Emily (Zoe Kazan) until a medical emergency grants him a newfound perspective.

Why it's so good: Nanjiani and his wife, Emily V. Gordon, penned the screenplay together, lending sincerity and emotional gravity to a movie inspired by their relationship.

"Top Five" (2014) emphasizes Chris Rock's talents as a writer, director, and star.

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Rosario Dawson and Chris Rock in "Top Five." Paramount Pictures

Synopsis: Comedian-turned-actor Andre Allen (Rock) finds his life choices called into question after he's followed around for a feature article by straight-shooting reporter Chelsea Brown (Rosario Dawson).

Why it's so good: Well-written and impressively acted, "Top Five" finds a sweet spot between vulnerable and funny as a standout film from writer-director Rock.

"To All The Boys I've Loved Before" (2018) is a light-hearted affair.

to all the boys
Noah Centineo and Lana Condor in "To All The Boys I've Loved Before." Netflix

Synopsis: When her love letters to numerous boys are released without her knowledge, Lara Jean Covey (Lana Condor) is confronted by her old crushes one by one.

Why it's so good: Based on Jenny Han's book of the same name, "To All The Boys I've Loved Before" takes tried-and-true elements of past rom-coms and pairs them with a likable young cast.

"Roman Holiday" (1953) is a delightful story elevated by Audrey Hepburn's performance.

Roman Holiday
Audrey Hepburn and Gregory Peck in "Roman Holiday." Paramount Pictures

Synopsis: Sheltered her whole life, Princess Anne (Hepburn) finds freedom in the streets of Rome as she falls for American reporter Joe Bradley (Gregory Peck) in the final leg of a goodwill tour.

Why it's so good: Arguably Hepburn's first prominent film role, "Roman Holiday" cemented the actresses' place as an iconic figure in Hollywood with a dazzling central performance.

"My Best Friend's Wedding" (1997) holds a mirror up to its own genre.

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Cameron Diaz and Julia Roberts in "My Best Friend's Wedding." TriStar Pictures

Synopsis: Days before her best friend Michael (Dermot Mulroney) is set to marry his fiancée (Cameron Diaz), New York food-critic Julianne Potter (Julia Roberts) flies across the country to profess her love before it's too late.

Why it's so good: Aided by a beloved cast and smart writing, "My Best Friend's Wedding" walks a fine line by indulging in romantic-comedy conventions while simultaneously deconstructing them.

"Love, Simon" (2018) is a crowd-pleasing coming-of-age story.

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Nick Robinson in "Love, Simon." 20th Century Fox

Synopsis: As he struggles to keep his sexuality hidden from his best friends, popular high schooler Simon Spier (Nick Robinson) connects with an anonymous classmate online.

Why it's so good: A warm-hearted coming-of-age movie based on Becky Albertalli's book, "Love, Simon" is a fun throwback to 1980s John Hughes films and paves the way for more untold love stories to come.

"The Best Man" (1999) is an entertaining feature with an impressive cast.

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Taye Diggs in "The Best Man." Universal Pictures

Synopsis: Novelist Harper Stewart (Taye Diggs) agrees to be the best man at his friend's (Morris Chestnut) wedding, but the weekend quickly unravels as Harper's latest book unearths old secrets.

Why it's so good: With a strong ensemble cast that includes actors like Terrence Howard, Harold Perrineau, and Nia Long, "The Best Man" provides laughs without ever compromising on its large cast of characters.

"Palm Springs" (2020) is a rom-com you'll want to see time and again.

palm springs
Cristin Milioti and Andy Samberg in "Palm Springs." Neon/Hulu

Synopsis: Disaffected maid of honor Sarah (Cristin Milioti) connects with a groomsman named Nyles (Andy Samberg) at her sister's wedding but is soon thrown for a loop by an unbelievable secret.

Why it's so good: The fun, hook-worthy plot and sharp humor in "Palm Springs" invites multiple viewings, leading rom-com fans to fall in love with Milioti and Samberg all over again.

"Stranger Than Fiction" (2006) is an unconventional romantic comedy.

stranger than fiction
Will Ferrell in "Stranger Than Fiction." Columbia Pictures

Synopsis: IRS Agent Harold Crick (Will Ferrell) wakes up one morning and hears an author (Emma Thompson) narrating his every move, causing him to soon realize he's the unwilling protagonist of her next book.

Why it's so good: An unconventional film in every sense of the word, "Stranger Than Fiction" is a high-concept movie grounded by a sweet romance between Harold and a baker named Ana (Maggie Gyllenhaal).

"Think Like a Man" (2012) is a book adaptation with a twist.

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The cast of "Think Like a Man." Matt Kennedy/Sony Screen Gems

Synopsis: Dominic (Michael Ealy) and his friends are blindsided when they realize the women they're dating are using the book "Act Like a Lady, Think Like a Man" to get what they want.

Why it's so good: An interesting anthology film broken down by its respective couples, "Think Like a Man" is a remarkably clever take on TV personality Steve Harvey's book.

"Punch-Drunk Love" (2002) is a romantic comedy with an oddball protagonist.

punch drunk love adam sandler
Luis Guzmán and Adam Sandler in "Punch-Drunk Love." Columbia Pictures

Synopsis: Shy by disposition but prone to angry outbursts, Barry Egan (Adam Sandler) tries to keep his temper under wraps as he navigates familial expectations, extortion, and newfound love.

Why it's so good: A romantic comedy electrified by underlying tension, "Punch-Drunk Love" is an enthralling vehicle for Sandler and a testament to Paul Thomas Anderson's range as a director.

"Easy A" (2010) is a winning comedy starring Emma Stone and Penn Badgley.

Easy A
Emma Stone in "Easy A." Screen Gems

Synopsis: Olive Penderghast (Emma Stone), a well-meaning high-school student, uses the rumor mill to her advantage when a salacious lie grows out of control.

Why it's so good: After a memorable performance in "Superbad" (2007), Stone charmed audiences by taking center stage in a movie that allowed her humor to really shine. Plus Badgley's turn as Woodchuck Todd is as endearing as ever.

Fate intervenes in the Candian rom-com "What If" (2014).

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Zoe Kazan and Daniel Radcliffe in "What If." CBS Films

Synopsis: Wallace (Daniel Radcliffe) feels like he's finally met the one when he befriends Chantry (Kazan), but her longtime boyfriend (Rafe Spall) would beg to differ.

Why it's so good: It can be hard to root for romantic plots that toe the line of cheating, but Radcliffe serves as a likable lead in this self-aware and emotionally earnest romantic comedy.

Note: "What If" was originally titled "The F Word" in several countries.

"The Half of It" (2020) is a gently told romance about loving yourself.

the half of it netflix
Leah Lewis and Daniel Diemer in "The Half of It." KC Bailey/Netflix

Synopsis: After noticing that straight-A student Ellie Chu (Leah Lewis) has a way with words, Paul Munsky (Daniel Diemer) recruits her help in impressing their mutual crush (Alexxis Lemire).

Why it's so good: Romantic-comedy fans looking for something unique will find that and more in "The Half of It," which promotes the idea that self-love is just as important as caring for someone else.

"The Holiday" (2006) wears its heart on its sleeve.

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Kate Winslet and Jack Black in "The Holiday." Columbia Pictures

Synopsis: Two love-lorn women, Amanda (Diaz) and Iris (Kate Winslet), are granted fresh perspectives when they trade houses over the holiday season and fall for Graham (Jude Law) and Miles (Jack Black).

Why it's so good: Unabashedly corny and predictable, "The Holiday" is a feel-good favorite that's as cozy and comforting as a holiday sweater and more self-aware than most critics give it credit for.

"Plus One" (2019) thrives off of its genuine dialogue and disarming cast.

plus one movie
Maya Erskine and Jack Quaid in "Plus One." Red Hour Films

Synopsis: Faced with a busy wedding season, college friends Alice (Maya Erskine) and Ben (Jack Quaid) decide to take each other as dates, but friendly banter soon grows into something more.

Why it's so good: With the help of a script that is as funny as it is sincere, "Plus One" is an underrated indie film that positions Erskine and Quaid as breakout stars.

"Set It Up" (2018) is a modern rom-com done right.

set it up
Zoey Deutch and Glen Powell in "Set It Up." Netflix

Synopsis: Overworked by their high-powered jobs, Harper (Zoey Deutch) and Charlie (Glen Powell) play matchmaker to get their bosses (Lucy Liu, Diggs) off their backs, but soon the young assistants start to fall for each other too.

Why it's so good: A modern hit that dabbles in genre tropes, "Set It Up" looks and feels familiar, but the charismatic cast and tight script keep it from ever seeming formulaic.

"Music and Lyrics" (2007) boasts a sweet love story and a strong soundtrack.

Hugh Grant Music and Lyrics
Drew Barrymore and Hugh Grant in "Music and Lyrics." Warner Bros. Pictures

Synopsis: After he's given the chance to collaborate with a rising star, washed-up 1980s icon Alex Fletcher (Hugh Grant) finds an unlikely writing partner in Sophie (Drew Barrymore).

Why it's so good: Fueled by Grant and Barrymore's believable chemistry and sweet banter, "Music and Lyrics" is an entertaining musical comedy with a phenomenal soundtrack to boot.

"Crazy, Stupid, Love" (2011) makes good use of its expansive cast.

emma stone crazy stupid love
Ryan Gosling and Emma Stone in "Crazy, Stupid, Love." Warner Bros. Pictures

Synopsis: After his wife (Julianne Moore) asks for a divorce, Cal Weaver (Steve Carell) recruits the help of Jacob Palmer (Ryan Gosling) in rebuilding his confidence to win her back.

Why it's so good: With a winding plot that keeps viewers engaged from start to finish, "Crazy, Stupid, Love" is a deceptively clever romantic comedy that takes full advantage of its hilarious ensemble cast.

A hopeless romantic heads for heartbreak in "500 Days of Summer" (2009).

500 days of summer
Joseph Gordon-Levitt and Zooey Deschanel in "500 Days of Summer." Fox Searchlight

Synopsis: When hopeless romantic Tom (Gordon-Levitt) falls for cynical Summer (Zooey Deschanel), he knows the relationship is doomed from the start, but that doesn't stop him from trying. `

Why it's so good: Surprisingly artful, "500 Days of Summer" delves into the harm of idealizing romantic partners and the joy of finding love after heartbreak.

"The Princess Bride" (1987) features a love story for the ages.

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Robin Wright and Cary Elwes in "The Princess Bride." 20th Century Fox

Synopsis: In the fantasy kingdom of Florin, Princess Buttercup (Robin Wright) and her love Westley (Cary Elwes) must fight their way back to each other as the nefarious Prince Humperdinck (Chris Sarandon) plots against them.

Why it's so good: A romantic comedy rife with notes of drama, intrigue, and swashbuckling action, "The Princess Bride" is a classic story based on William Goldman's novel that encapsulates multiple genres without ever missing a beat.

Two teenagers kick-start a road trip in "Y tu mamá también" (2001).

y tu mama tambien IFC Films
Maribel Verdú, Diego Luna, and Gael García Bernal in "Y tu mamá también." IFC Films

Synopsis: In 1990s Mexico, Julio (Gael García Bernal) and Tenoch (Diego Luna) set off on a spontaneous road trip with Luisa Cortés (Maribel Verdú), an older woman that they both fall madly in love with.

Why it's so good: The Spanish-language film often dips into romantic-drama territory, but "Y tu mamá también" is kept light by its frequent jokes and director Alfonso Cuarón's breathless pacing.

"Celeste and Jesse Forever" (2012) has humor and heart.

Celeste and jesse forever
Rashida Jones and Andy Samberg in "Celeste and Jesse Forever" Sony Pictures Classics

Synopsis: After marrying too young, Celeste (Rashida Jones) and Jesse (Samberg) split up and decide to stay close. But as they start dating new people, their friendship throws a wrench in their love lives.

Why it's so good: Hilarious and heartbreaking in equal measure, "Celeste and Jesse Forever" proves that Samberg and Jones have the dramatic heft to carry an emotionally layered film.

"Jerry Maguire" (1996) is known for its iconic dialogue.

jerry maguire tri star pictures
Renée Zellweger and Tom Cruise in "Jerry Maguire." Tri-Star Pictures

Synopsis: After getting fired, high-profile sports agent Jerry Maguire (Tom Cruise) tries to start his own agency with the help of single mother Dorothy Boyd (Renée Zellweger).

Why it's so good: With a wealth of emotion brimming on the surface and memorable lines like "You had me at hello" and "You complete me," this highly quotable romantic comedy is difficult to forget.

"Obvious Child" (2014) creates a believable romance while empowering its protagonist.

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Jenny Slate in "Obvious Child." Chris Teague via Sundance Institute

Synopsis: An unemployed stand-up comedian named Donna (Jenny Slate) tries to find humor in a bleak situation when a fun fling with a grad student (Jake Lacy) results in an unplanned pregnancy.

Why it's so good: Through the lens of its relatable protagonist, "Obvious Child" destigmatizes the conversation on birth control and abortion while fostering a gentle romance between Lacy and Slate.

"Love and Basketball" (2000) is a smart sports film that allows its characters to grow.

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Sanaa Lathan and Omar Epps in "Love and Basketball." New Line

Synopsis: Childhood friends Monica (Sanaa Lathan) and Quincy (Omar Epps) set their sights on playing professional basketball as their career paths threaten to pull them apart.

Why it's so good: With commentaries on gender, competition, and growth, "Love and Basketball" covers a lot of ground without ever losing sight of its main couple.

"High Fidelity" (2000) hides optimism beneath all of its snark.

high fidelity
John Cusack in "High Fidelity." Touchstone Pictures

Synopsis: Record-shop owner Rob Gordon (John Cusack) knows everything about music but can't seem to figure out love. As he looks back on his biggest breakups, he mulls over what went wrong with Laura (Iben Hjejle), the one that got away.

Why it's so good: Based on the book by Nick Hornby, "High Fidelity" is a satire built on snark and skepticism, but it also leaves room for a joyful ending that could make even the most stubborn cynic smile.

Opposites attract in "The Shop Around the Corner" (1940).

the shop around the corner
James Stewart and Margaret Sullavan in "The Shop Around the Corner." MGM

Synopsis: Alfred Kralik (James Stewart) and Klara Novak (Margaret Sullavan) butt heads at the gift shop where they work in Budapest, unaware that they've been writing to each other as anonymous pen pals.

Why it's so good: Stewart and Sullivan are in top form, and fans of "You've Got Mail" (1998) will enjoy seeing where the feature pulled inspiration from.

"Leap Year" (2010) is a sweet and simple romantic comedy set in Ireland.

Leap Year
Amy Adams in "Leap Year." Universal Pictures

Synopsis: Anna Brady (Amy Adams) hops on a plane to Ireland so she can propose to her boyfriend (Adam Scott) on Leap Day, but she soon gets stuck in Dingle with handsome innkeeper Declan (Goode).

Why it's so good: With its gorgeous Irish backdrops and bewitching leads, "Leap Year" is top-tier turn-your-brain-off entertainment for rom-com fans looking to be whisked away.

A mix-up leads to mistaken identity in "Man Up" (2015).

man up
Simon Pegg and Lake Bell in "Man Up." Saban Films

Synopsis: After a misunderstanding lands Nancy (Lake Bell) in the middle of a blind date with Jack (Simon Pegg), she rolls with the punches and pretends to be another woman.

Why it's so good: Blind date mix-ups have been done before and will no doubt be done again, but "Man Up" feels funny and fresh enough to forgive a few predictable plotlines.

Randall Park and Ali Wong have amazing chemistry in "Always Be My Maybe" (2019).

always be my maybe
Randall Park and Ali Wong in "Always Be My Maybe." Netflix

Synopsis: Celebrity chef Sasha Tran (Wong) returns to her home city of San Francisco to discover that a spark still remains between her and her childhood sweetheart Marcus Kim (Park).

Why it's so good: Wong and Park's infectious charm spills off the screen in a romantic comedy that's as lovable as its two lead stars.

"They Came Together" (2014) pokes fun at romantic comedies as a whole.

they came together
Paul Rudd and Amy Poehler in "They Came Together." Lionsgate

Synopsis: Candy-shop owner Molly (Amy Poehler) and corporate executive Joel (Paul Rudd) couldn't be more different, but a chance encounter soon turns the bickering duo into inseparable soul mates.

Why it's so good: "They Came Together" ironically lampoons the very genre that jump-started Rudd's career, and sharp-eyed fans will enjoy seeing all the fun references and nods to classic rom-coms throughout.

Two friends fight their mutual attraction in "Sleeping With Other People" (2015).

Sleeping With Other People
Alison Brie and Jason Sudeikis in "Sleeping With Other People." IFC Films

Synopsis: Two unlucky-in-love New Yorkers — Lainey (Alison Brie) and Jake (Jason Sudeikis) — fight an instant attraction for each other as they try to keep their newfound relationship platonic.

Why it's so good: Sudeikis and Brie are well-matched in this surprisingly tender, fast-talking comedy from writer-director Leslye Headland.

A famous actress falls for a bookshop owner in "Notting Hill" (1999).

notting hill screenshot
Julia Roberts in "Notting Hill." Polygram Filmed Entertainment

Synopsis: Bookshop owner William Thacker (Grant) can't believe his eyes when American actress Anna Scott (Roberts) visits his store in London, and their meet-cute soon turns into a full-fledged affair.

Why it's so good: Even the wittiest romantic comedy is nothing without strong chemistry, and Roberts and Grant share it in spades.

"Bend It Like Beckham" (2002) is a feel-good sports film that never gets old.

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Keira Knightley and Parminder Nagra in "Bend It Like Beckham." Fox Searchlight Pictures

Synopsis: London teens Jess (Parminder Nagra) and Jules (Keira Knightley) set their sights on professional football careers against their parent's wishes, all while Jess is falling for her coach (Jonathan Rhys Meyers).

Why it's so good: Nagra plays an easy lead to cheer for in this uplifting underdog story about following your dreams and falling in love along the way.

"While You Were Sleeping" (1995) wouldn't be the same without Sandra Bullock.

sandra bullock while you were sleeping
Sandra Bullock in "While You Were Sleeping." Hollywood Pictures

Synopsis: After saving an unconscious Peter (Peter Gallagher) on the subway platform, token taker Lucy (Bullock) is mistaken for his fiancée at the hospital, which complicates things when she starts to fall for his brother, Jack (Bill Pullman).

Why it's so good: With a plot that could only exist in the realm of romantic comedies, "While You Were Sleeping" fully embraces its quirks and elevates Bullock's endless charm.

"It Happened One Night" (1934) continues to influence romantic comedies today.

It Happened One Night movie 1934 Best picture
Claudette Colbert in "It Happened One Night." Columbia

Synopsis: After rebellious heiress Ellie Andrews (Claudette Colbert) marries a man against her father's wishes and is torn away from her husband, she crosses paths with a newspaper reporter (Clark Gable) who offers to reunite the two mismatched lovers.

Why it's so good: "It Happened One Night" is one of the earliest examples of romantic comedies, and its classic story elements — love triangles, runaway brides, and jerks with a heart of gold — continue to endure in the genre today.

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