SPOILERS

Romantic Comedies have become a bit of a downer as of late. In fact, it seems like a dying film genre. Critics rip them to shreds unless the filmmakers find ways to cross their story over into other genres deemed acceptable (and even then it “typically” only gets mediocre reviews). If the couple doesn’t end up together, then it has a higher chance of being critically accepted (500 Days of Summer). Or if the romantic male lead as a character is more realistic and looks like your average Joe, it also has a higher chance of being accepted (Knocked Up). Are the jokes cruder? The women more politically correct? Does the romantic comedy appeal to a male demographic?

These seem to be the checklist for many of the recent romantic comedies.

Now I’m not here to argue whether or not these films are good. That’s not my point. Rather, I’m here to argue in the favor of traditional romantic comedies that don’t have to cross over into so many other genres to actually get made. Don’t get me wrong, I’m all for genre crossing (you’ll definitely see a bunch on this list), but that doesn’t mean we shouldn’t also be able to create conventional romantic comedies as well.

Right now, let’s just say romantic comedies are no longer the popular kid in class!

And why is that? Fans of the genre are told that romantic films and fairy tales are bad for us. They make us long for unrealistic and completely unattainable relationships. I’m sure you’ve heard the arguments. So do people simply assume that we are too silly minded to understand the difference between fantasy and reality? Romantic Comedies are a subgenre of happily ever after fairytales, after all…

What then of action films clearly geared to a male demographic? What of the female characters in action films? I don’t know about you, but these women don’t seem particularly realistic. They have perfect bodies, perfect hair, they kickass like a ninja while also still needing the man to rescue them. Um….what?

Personally, I don’t watch a romantic comedy for realism. I’m pretty sure most people say the same thing about these action flicks I mentioned or the latest superhero blockbuster. Rather, I watch them because I think they’re entertaining. I like escapist romances. It’s a genre of film that deserves more respect than it actually gets. Take a look at all those really crappy romantic comedies out there, for instance. Proof it’s not so easy to pull one off.

So, I thought it would be fun to celebrate great romantic comedies.

While perhaps unrealistic and at times quite formulaic, the Hollywood recipe for the romantic comedy always tastes good when cooked to a simmering perfection. Some may be a delicious dessert, while others make for quite the fancy feast. Whatever the case may be, it’s high time we stop feeling ashamed for enjoying a good old-fashioned romantic comedy.

For my list, while some of the romantic comedies cross over into other genres (musical, situational comedy, action, fantasy and even dramedy), the films mainly focus on the romance between the main couple and the obstacles between them. Not only that, the film has to be funny. So there are some great romances out there, but that doesn’t necessarily mean they’re a romantic comedy. There is such a thing as a romantic drama!

What you won’t find are a few of the popular ones from the last few years, because I think many of them are a new subgenre of romantic comedies that perhaps cross a little TOO far over into the crude comedy path, driven more to a teenage male demographic.

In all, I tried to pick a variety of romantic comedies, from classic to modern-day, that represent some of the best cinema has to offer.

So without further ado, here are some of the best romantic comedies of all time. I’ll list the first 50 this week and the final 50 in the near future!

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THE 100 BEST ROMANTIC COMEDIES OF ALL TIME (in no particular order)

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#1 You’ve Got Mail

Year: 1998

Director: Nora Ephron

Starring: Meg Ryan and Tom Hanks

My Take: Influenced by Pride and Prejudice (more of a romantic drama, so no adaptations made the list) and Shop Around the Corner, this tale of competing book lovers is the ultimate romantic comedy showing everyone how to do the genre right. It’s witty, entertaining and yes, romantic. Not to mention the perfect casting of Tom Hanks and Meg Ryan. If you want to be reminded of why romantic comedies are awesome, watch this memorable classic!

#2 It Happened One Night

Year: 1934

Director: Frank Capra

Starring: Clark Gable and Claudette Colbert

My Take: This is romantic comedy at its best (even winning some Oscars) as a spoiled young heiress runs away from home (or at least her father) to get to her “husband” in New York City. Along the way, she enlists the help of a reporter who wants the exclusive on her story. Of course, you can guess what happens next…

#3 Sleepless in Seattle

Year: 1993

Director: Nora Ephron

Starring: Tom Hanks and Meg Ryan

My Take: There’s something magical about the duo of Tom Hanks and Meg Ryan. Together they’re able to create movie magic. Sleepless in Seattle manages to pull off a clever, witty, romantic comedy without the two actually meeting until the end. Still, it remains one of the best classic romantic comedies of all time. It really is both incredibly romantic while also being incredibly funny. Plus, it’s nice to see two leads with such an amazing chemistry.

#4 While You Were Sleeping

Year: 1995

Director: Jon Turteltaub

Starring: Sandra Bullock and Bill Pullman

My Take: This movie really helped audiences fall in love with Sandra Bullock. If there’s one thing she’s great at, it’s the romantic comedy genre. She’s able to pull off the All American good girl charm with a combination of likability and vulnerability. And what makes me love this romantic comedy in particular is that ultimately it’s about loneliness. Lucy is such a real character and we root for her to find the happiness she deserves. Moreover, while Bill Pullman isn’t your typical leading man, he’s exactly right for the role. There’s nothing not to love about this film that has comedy, romance and even a little heartbreak.

#5 When Harry Met Sally

Year: 1989

Director: Rob Reiner

Starring: Meg Ryan and Billy Crystal

My Take: This may be one of the most popular romantic comedies…ever. While it’s not my personal favorite (I still really liked it), Nora Ephron proved time and time again that she was the queen of writing romantic comedies. This film asks the age old question: Can men and women ‘just’ be friends? Meg Ryan and Billy Crystal had a fun chemistry which worked well with the memorable script.

#6 Breakfast At Tiffany’s

Year: 1961

Director: Blake Edwards

Starring: Audrey Hepburn and George Peppard

My Take: Despite a few strange racist moments in the film, this movie is pure romantic comedy gold. It’s funny, classy and unforgettable. Plus, it’s Audrey Hepburn at her most memorable. Not to mention the music classic “Moon River” and the amazing kiss in the rain. What’s not to love?

#7 Notting Hill

Year: 1999

Director: Richard Curtis

Starring: Julia Roberts and Hugh Grant

My Take: This story of a movie star who falls in love with a bookshop owner, follows all the romantic comedy cliches, but somehow never feels tired or obvious. It’s filled with so much charm (in part thanks to the witty script) and sincerity that it’s hard not to love this film. It truly is one of the greatest romantic comedies of all time.

#8 Love Actually

Year: 2003

Director: Richard Curtis

Starring: Colin Firth, Keira Knightley, Bill Nighy, Emma Thompson, Hugh Grant, Liam Neeson, Andrew Lincoln, etc.

My Take: While I didn’t love “every” romance included in this film, for the most part, the interweaving story lines and love stories are simply entertaining. And who doesn’t love Colin Firth?

#9 Bridget Jones’s Diary

Year: 2001

Director: Sharon Maguire

Starring: Renee Zellweger, Colin Firth and Hugh Grant

My Take: There’s so many reasons to love this romantic comedy, I can’t even count. But here’s a few: One, Colin Firth makes a glorious return to his most beloved role as Mr. Darcy. Two, every time Hugh Grant enters the screen the film becomes hysterically funny. Three, Bridget Jones is pure awkwardness and hilarity as she finds herself in the most humiliating scrapes. And finally, it’s very romantic. Honestly, the film just gets funnier and funnier each time I watch.

#10 Pretty Woman

Year: 1990

Director: Garry Marshall

Starring: Richard Gere and Julia Roberts

My Take: A romantic comedy power duo, Gere and Roberts shined onscreen together in this Cinderella-esque fairy tale of a prostitute who finds love with a wealthy businessman.

#11 Runaway Bride

Year: 1999

Director: Garry Marshall

Starring: Julia Roberts and Richard Gere

My Take: What I love about Runaway Bride is that it is a pure, traditional romantic comedy and a great one at that. It doesn’t hurt that there’s a great chemistry between the leads of course either. The concept was fun, it had a great soundtrack, the supporting characters were funny, not to mention there was a real underlying substance here. Maggie as a character has some real flaws and problems. And it’s actually kind of sad how the people in her town treat her. And that’s something a lot of romantic comedies that fall short forget – you can’t just follow the formula of a romantic comedy and expect it to be good. The characters need to have some actual depth. And this one does it well in a very funny and entertaining way. Comedy is usually at its best when it’s capturing some real truth about humanity.

#12 Never Been Kissed

Year: 1999

Director: Raja Gosnell

Starring: Drew Barrymore and Michael Vartan

My Take: I don’t know about anyone else but I never had an English teacher that cute! This romantic comedy about an awkward undercover reporter who has never been kissed (and falls in love with the English teacher of the high school she’s undercover at) is charming and VERY romantic. Josie’s epic first kiss is one of the most amazing cinema kisses…ever.

#13 Miss Congeniality

Year: 2000

Director: Donald Petrie

Starring: Sandra Bullock and Benjamin Bratt

My Take: This is actually one of my personal favorites. It’s one of those movies you can watch over and over and still laugh every time. Plus, there was something dreamy about Benjamin Bratt as Gracie’s partner that made it easy to root for them. Not to mention their banter was just so much fun to watch. I like to pretend the sequel doesn’t exist.

#14 Amelie

Year: 2001

Director: Jean-Pierre Jeunet

Starring: Audrey Tautou and Mathieu Kassovitz

My Take: This movie is quirky, delightful, original and of course, romantic. This tale of a shy woman who spends her time helping others and finds love along the way is a charming story. There’s nothing else quite like Amelie and I can’t recommend it enough. It’s refreshing to watch a movie about a female character who is extremely introverted.

#15 Pillow Talk

Year: 1959

Director: Michael Gordon

Starring: Doris Day and Rock Hudson

My Take: This rom-com is hilarious from start to finish – and it doesn’t hurt that Day and Hudson are simply magical onscreen together. They really know how to play off each other well while playing up both the comedy and the romance. It’s the go to love/hate relationship that we can’t help but love.

#16 Bend it Like Beckham

Year: 2002

Director: Gurinder Chadha

Starring: Parminder Nagra and Jonathan Rhys Meyers

My Take: Bend it Like Beckham explores the idea of reaching for your dreams even if it doesn’t suit the interests of your parents. So while Jess pursues soccer secretly against the wishes of her family, she also falls in love with her very handsome coach who believes in her. I saw this movie in the theater twice and both times two different audiences gasped at the same time. The scene in question? When Joe (Jonathan Rhys Meyers) shows up at her doorstop to talk to her and turns around. It’s the first time we see him out of his coach uniform (or at least that’s what I remember) and he looks very different and very romantic. By that point, the audience knew where the story was going. Their love story is one for the books for sure.

#17 Return to Me

Year: 2000

Director:  Bonnie Hunt

Starring: David Duchovny and Minnie Driver

My Take: Return to Me is proof that one, Bonnie Hunt should direct more films. And two, that David Duchovny is the perfect leading man. Though I admit to only saying that (mostly) based on the mere fact that I want to marry Mulder. Kidding aside, this story is both tragic and funny. The first part of the film will have you in tears when Bob’s first wife tragically dies in an accident, only to laugh often in the next part when he falls unknowingly with the woman who received his wife’s heart in a transplant. This film is perfectly sweet without going into cheesy territory. It’s truly a wonderful film.

#18 Two Weeks Notice

Year: 2002

Director: Marc Lawrence

Starring: Sandra Bullock and Hugh Grant

My Take: This is one of those traditional romantic comedies that isn’t afraid to fully embrace what it is, which in this case really works in its favor. Bullock and Grant together are one of my favorite romantic comedy duos. Both of them are comedic geniuses, so when they come together it’s comedy at it’s best. Then throw in the romance and it’s romantic comedy at it’s best. Again, there’s something about Hugh Grant that puts me in stitches. And Sandra Bullock is always funny and always likable.

#19 The American President

Year: 1995

Director: Rob Reiner

Starring: Michael Douglas and Annette Bening

My Take: It’s a classic boy falls in love with girl story, you know except that the boy happens to be the President of the United States. With these two, sparks fly right from the start. The movie is romantic and funny with great storytelling to support what makes for a fantastic film.

#20 Harold and Maude

Year: 1971

Director: Hal Ashby

Starring: Ruth Gordon and Bud Cort

My Take: This may well be the strangest romantic comedy of them all. It’s dark and unusual about a young man obsessed with death who befriends and falls for a 79-year-old woman at a funeral. It’s a fabulous film everyone should check out.

#21 Annie Hall

Year: 1977

Director: Woody Allen

Starring: Woody Allen and Diane Keaton

My Take: This Oscar winning romantic comedy is one of Woody Allen’s finest films with Diane Keaton at her neurotic best. A classic for sure with witty fast talking dialogue and memorable characters.

#22 City Lights

Year: 1931

Director: Charlie Chaplin

Starring: Charlie Chaplin and Virginia Cherrill

My Take: I loved this beautiful silent film about the Tramp who falls in love with a blind girl. It’s charming, funny and beautifully made.

#23 The Princess Bride

Year: 1987

Director: Rob Reiner

Starring: Cary Elwes and Robin Wright

My Take: Also a fantasy and a fairy tale, this romantic comedy is sure to always be a fan favorite. Besides the many memorable quotes, the romance is one for the story books…literally.

#24 Kate and Leopold

Year: 2001

Director: James Mangold

Starring: Meg Ryan and Hugh Jackman

My Take: Kate and Leopold is pure romantic fun! Hugh Jackman plays the epitome of the perfect man we love to fantasize about. Not only is he handsome, charming, intelligent, chivalrous and kind, but he’s also from a different time period. So it’s fun to watch our “Mr. Darcy” fantasy unfold in the modern world. In all, Leopold makes the ideal leading man in one of the most entertaining traditional romantic comedies.

#25 The Holiday

Year: 2006

Director: Nancy Meyers

Starring: Kate Winslet, Jack Black, Cameron Diaz and Jude Law

My Take: Perhaps because I relate quite a bit to the two female characters, or maybe because I absolutely adore Jude Law, this is one of my favorites. There’s something charming about this tale about two different women who go on vacation from their lives only to find love.

#26 Romancing the Stone

Year: 1984

Director: Robert Zemeckis

Starring: Michael Douglas and Kathleen Turner

My Take: This romantic comedy blends itself into a real life romance novel type adventure when a shy romance novelist goes to Colombia to rescue her kidnapped sister and finds herself stuck on an adventure with an adventurous bad boy. It’s a lot of fun with many laugh out loud moments.

#27 Much Ado About Nothing

Year: 1993

Director: Kenneth Branagh

Starring: Emma Thompson, Kenneth Branagh, Kate Beckinsale and Robert Sean Leonard

My Take: The first time I watched this particular Shakespeare adaptation from Branagh, I laughed so hard I had tears rolling down my face. It’s hard to top the romantic and comedic chemistry between Emma Thompson and Kenneth Branagh as the notorious Beatrice and Benedick. They perfected Shakespeare’s (who really was ahead of his time) romantic comedy for the silver screen.

#28 His Girl Friday

Year: 1940

Director: Howard Hawks

Starring: Cary Grant and Rosalind Russell

My Take: This fast talking romantic comedy classic is certainly one of the greatest of all time with Cary Grant and Rosalind Russell at the top of their game. Hawks certainly knows how to do romantic comedy well in this story of two reporters in the midst of a divorce.

#29 Penelope

Year: 2006

Director: Mark Palansky

Starring: Christina Ricci and James McAvoy

My Take: This wonderful film (though it’s even better with the longer, full European release) doesn’t get as much love as it deserves. The story about a young woman with a pig nose who can only break her family’s curse when a blue blood loves her for who she is, perfectly blends the Beauty and the Beast fairy tale with a romantic comedy. It’s funny and delightful with James McAvoy as the perfect leading man.

#30 Singin’ in the Rain

Year: 1952

Directors: Stanley Donen and Gene Kelly

Starring: Gene Kelly and Debbie Reynolds

My Take: Both romantic comedy and classic musical, this is one of the best films of all time with an unforgettable soundtrack, iconic dance moves and a memorable romance with a lot of humor thrown into the mix.

#31 Populaire

Year: 2012

Director: Régis Roinsard

Starring: Déborah François and Romain Duris

My Take: This lesser known French period gem tells the story of Rose, a young secretary who’s horrible at her job but is also a master typist. Her handsome boss trains her to become the best and enters her into competitions. Of course, a romance develops between the two. I can’g gush about how cute this film is!

#32 The Philadelphia Story

Year: 1940

Director: George Cukor

Starring: Cary Grant, Katharine Hepburn and Jimmy Stewart

My Take: A romantic triangle done well…When Tracy’s ex-husband as well as a reporter show up before her wedding all kinds of craziness ensues! This is a must watch film including fantastic performances from some of the greatest actors of all time.

#33 Something’s Gotta Give

Year: 2003

Director: Nancy Meyers

Starring: Diane Keaton and Jack Nicholson

My Take: Nicholson and Keaton shine on screen together in a film that’s funny from start to finish. The story of an aging playboy who finally falls in love with a woman his own age is both endearing as well as hilarious.

#34 The Awful Truth

Year: 1937

Director: Leo McCarey

Starring: Irene Dunne and Cary Grant

My Take: Part screwball, this romantic comedy about a couple on the verge of divorce had me in stitches for the entire duration. The two try to sabotage each other’s attempt at new romances before their divorce becomes final and it is a lot of fun to watch.

#35 Groundhog Day

Year: 1993

Director: Harold Ramis

Starring: Andie MacDowell and Bill Murray

My Take: A wonderful film about a weatherman who keeps experiencing the same day on repeat. Thankfully, in the process he’s able to fall in love.

#36 I Know where I’m Going!

Year: 1945

Directors: Michael Powell and Emeric Pressburger

Starring: Wendy Hiller and Roger Livesey

My Take: A lesser known romantic comedy that takes place in the Scottish Highlands and is steeped in Scottish folklore. It’s a beautiful film everyone should check out.

#37 10 Things I Hate About You

Year: 1999

Director: Gil Junger

Starring: Heath Ledger, Julia Styles, Joseph Gordon-Levitt and Larisa Oleynik

My Take: This modern retelling of The Taming of the Shrew is one of the best teen romantic comedies ever. Plus, it has a young Heath Ledger singing and dancing so as to woo the “shrew” Kat, which is always great on a re-watch!

#38 Shakespeare Retold: The Taming of the Shrew

Year: 2005

Director: David Richards

Starring: Rufus Sewell and Shirley Henderson

My Take: Also a modern retelling of Taming of the Shrew, this adaptation is HILARIOUS. The chemistry between the two sizzles while the laughs never stop. It’s one funny scene after another, while also being completely romantic. If you haven’t seen it, check the film out right away.

#39 Roman Holiday

Year: 1953

Director: William Wyler

Starring: Gregory Peck and Audrey Hepburn

My Take: The story of a princess who runs away from home to experience the real world is an unforgettable one. Soon, she falls for an American newspaper man, but can they really have their happy ending? I loved this little fairy tale of a film for all it’s charm and humor.

#40 My Big Fat Greek Wedding

Year: 2002

Director: Joel Zwick

Starring: Nia Vardalos and John Corbett

My Take: This breakout hit has become one of the most popular romantic comedies ever and was even nominated for Best Original Screenplay at the Academy Awards. The script (also from star Vardalos) is clever, witty, funny and memorable.

#41 As Good As It Gets

Year: 1997

Director: James L. Brooks

Starring: Jack Nicholson and Helen Hunt

My Take: Helen Hunt and Jack Nicholson give great performances in this romantic dramedy and won the best Actor awards to prove it. It’s both funny and an oddly romantic story about a waitress and the bigoted OCD guy she serves.

#42 Adam’s Rib

Year: 1949

Director: George Cukor

Starring: Spencer Tracy and Katharine Hepburn

My Take: One of cinema’s greatest onscreen duos, Hepburn and Tracy sparkle in this story of dueling lawyers who just so happen to also be married.

#43 The Cutting Edge

Year: 1992

Director: Tony Gilroy

Starring: D.B. Sweeney and Moira Kelly

My Take: I’ve always loved this traditional romantic comedy that plays into the familiar story of two people who’s hate for each other slowly turns to love. The story brings together a figure skater and a hockey player to become pair skaters and of course at first they clash. The ending leads to a fantastic performance that always made me more interested in pair skating at the Olympics and what kind of daring feats they’d attempt.

#44 Silver Linings Playbook

https://www.youtube.com/watch?v=Lj5_FhLaaQQ

Year: 2012

Director: David O. Russell

Starring: Bradley Cooper and Jennifer Lawrence

My Take: With an Oscar winning performance from Jennifer Lawrence, an Oscar nominated performance from Bradley Cooper, a fantastic script with wonderful direction, this is not a romantic comedy to ignore. However, don’t be fooled by all the awards it received, it’s still a traditional romantic comedy in every way with wonderfully odd main characters who struggle with personal demons and even mental illness.

#45 The Importance of Being Earnest

Year: 2002

Director: Oliver Parker

Starring: Rupert Everett, Colin Firth, Reese Witherspoon and Frances O’Connor

My Take: This romantic comedy based on Oscar Wilde’s play is a hilarious comedy of two friends using the same pseudonym (Ernest) to romance women. It’s great fun with a brilliant cast.

#46 Say Anything

Year: 1989

Director: Cameron Crowe

Starring: John Cusask and Ione Skye

My Take: This popular romantic comedy about Lloyd Dobler, who’s attempt to date valedictorian Diane Court the summer before she goes off to college, is a real classic with lots of iconic scenes and memorable moments.

#47 Moonstruck

Year: 1987

Director: Norman Jewison

Starring: Cher and Nicolas Cage

My Take: Loretta falls for the brother of her fiance and what follows is a passionate love story including one of Cher’s greatest performances. Cher and Cage have some surprisingly good chemistry.

#48 Something New

Year: 2006

Director: Sanaa Hamri

Starring: Sanaa Lathan and Simon Baker

My Take: This is a smart romantic comedy about an uptight CPA and a free spirited landscaper who fall in love, despite her reservations because he’s white. I enjoyed every minute of this film, in part because of the two’s chemistry and also, Simon Baker is a bit dreamy isn’t he?

#49 Four Weddings and A Funeral

Year: 1994

Director: Mike Newell

Starring: Hugh Grant and Andie MacDowell

My Take: It’s hard not to love this romantic comedy about a British bachelor who falls in love with an American, especially when they share an amazing kiss in the rain.

#50 Sabrina 

Year: 1995

Director: Sydney Pollack

Starring: Harrison Ford, Julia Ormond and Greg Kinnear

My Take: This charming remake follows Sabrina who undergoes a major personal transformation and ends up winning the hearts of two brothers. This movie is very funny and also incredibly romantic. It’s worth watching again and again.

#51 Sabrina 

Year: 1954

Director: Billy Wilder

Starring: Humphrey Bogart, Audrey Hepburn and William Holden

My Take: The classic love triangle between Linus, Sabrina and David is very entertaining to watch and is still one of my favorites. I can never decide which one I love more. This one or the remake.

#52 13 Going on 30

Year: 2004

Director: Gary Winick

Starring: Jennifer Garner and Mark Ruffalo

My Take: Thirteen-year-old Jenna plays a game on her birthday and wakes up as a 30 year-old woman. What then unfolds is a love story about best friends in an adorable and really romantic film. The story takes some unexpected twists but has the perfect ending! The best part? The “Thriller” dance.

#53 Holiday 

Year: 1938

Director: George Cukor

Starring: Cary Grant and Katharine Hepburn

My Take: A Grant and Hepburn classic, the films tells the story of Johnny who falls in love with a very rich woman. But is she the right one for him?

#54 Clueless

Year: 1995

Director: Amy Heckerling

Starring: Alicia Silverstone and Paul Rudd

My Take: A modern retelling of Jane Austen’s Emma, this charming film is filled with humor, pop culture and lots of romance. It’s a ’90s classic for sure.

#55 The Lady Eve

Year: 1941

Director: Preston Sturges

Starring: Henry Fonda and Barbara Stanwyck

My Take: Card sharps target the heir (and snake expert) Charles on a ship, that is until Jean – one of the card sharps – falls in love with him. Unfortunately, when he learns the “truth” he angrily dumps her. To get her revenge, she returns by masquerading as an English lady to torture him. It’s a very romantic film with a lot of humor thrown into the mix.

Fun Fact: The ‘tripping’ scene in The Lady Eve is one of our Best Meet-Cutes of All Time.

#56 Sixteen Candles

Year: 1984

Director: John Hughes

Starring: Molly Ringwald and Michael Schoeffling

My Take: A John Hughes classic, this romantic comedy tells the story of Samantha, who has everything bad happen to her on her sixteenth birthday. But her tables turn when her crush, the most popular boy in school, Jake Ryan, discovers her feelings. While there are a few questionable moments in the film, the romance between Jake and Samantha still make teen girl’s hearts soar everywhere and it always makes for a fun re-watch. Especially the ending…

#57 Jerry Maguire

Year: 1996

Director: Cameron Crowe

Starring: Tom Cruise and Renee Zellweger

My Take: It’s hard to top the “you complete me” speech given from Jerry to Dorothy, the only woman who believes in him.

#58 Strictly Ballroom

Year: 1992

Director: Baz Luhrmann

Starring: Paul Mercurio and Tara Morice

My Take: Dirty Dancing meets Moulin Rouge, this quirky romantic dance comedy from Baz Luhrmann is one of my personal favorites.

#59 Sweet Home Alabama

Year: 2002

Director: Andy Tennant

Starring: Reese Witherspoon and Josh Lucas

My Take: This traditional romantic comedy about a southern woman trying to escape her past is pure fun! Who knew lightning could be so romantic…

#60 Emma

Year: 1996

Director: Douglas McGrath

Starring: Gwyneth Paltrow and Jeremy Northam

My Take: A young Gwyneth Paltrow shines in this film adaptation of Jane Austen’s classic novel romantic comedy style. Jeremy Northam made the perfect Mr. Knightley with the perfect blend of wit and old-fashioned charm.

#61 The Bachelor and the Bobby-Soxer

Year: 1947

Director: Irving Reis

Starring: Cary Grant, Shirley Temple and Myrna Loy

My Take: A screwball romantic comedy about the teenager Susan, who falls in love with the playboy Richard, only for him to fall in love with her sister Margaret who is a Judge (who orders him to pretend to date Susan until she gets over her crush instead of going to prison). If you haven’t seen this film, it is hilarious.

#62 Some Kind of Wonderful

Year: 1987

Director: Howard Deutch (written by John Hughes)

Starring: Eric Stoltz, Lea Thompson and Mary Stuart Masterson

My Take: For all the romantics out there who believe the best kind of love stems from friendship…

#63 Swing Time

Year: 1936

Director: George Stevens

Starring: Ginger Rogers and Fred Astaire

My Take: A Fred and Ginger romantic comedy classic! This film includes some of the best dance sequences of all time.

#64 My Man Godfrey (1936)

Year: 1936

Director: Gregory La Cava

Starring: William Powell and Carole Lombard

My Take: This romantic comedy about a socialite who hires a homeless man (with a mysterious past) to be her family’s butler (who she then falls in love with) is a must see.

#65 My Best Friend’s Wedding

Year: 1997

Director: P.J. Hogan

Starring: Julia Roberts, Dermot Mulroney, Cameron Diaz and Rupert Everett

My Take: While I personally didn’t love the ending, the film as a whole is quite memorable and a wonderful romantic comedy to watch again and again.

#66 How To Marry A Millionaire

Year: 1953

Director: Jean Negulesco

Starring: Marilyn Monroe, Lauren Bacall, Betty Grable

My Take: Three struggling women try to find millionaires to marry, but end up finding real love instead. If you love these three actresses, then this film is a must see.

#67 Pretty in Pink

Year: 1986

Director: Howard Deutch (John Hughes the writer)

Starring: Molly Ringwald, Andrew McCarthy and Jon Cryer

My Take: This star-crossed teen love story about Andie and Blane, two teenagers from opposites sides of the track, is a John Hughes classic with heart and humor.

#68 The Pirate

Year: 1948

Director: Vincente Minnelli

Starring: Judy Garland and Gene Kelly

My Take: This musical, romantic comedy starring Judy Garland and Gene Kelly about a girl who falls in love with the idea of the infamous pirate Macoco is great fun.  The story gets even more fun (and ridiculous) when a singer falls in love with the girl and pretends to be said legendary pirate. This is a lesser known gem worth watching.

#69 Austenland

Year: 2013

Director: Jerusha Hess

Starring: Keri Russell and JJ Feild

My Take: If you take this film too seriously, then you probably won’t enjoy it. However, if you go into this satirical romantic comedy and fully embrace the silliness, you may love it as much as I did. Plus, how perfect was the casting of Keri Russell as Jane who just so happens to be obsessed with an unattainable crush (aka Mr. Darcy)?

#70 Woman of the Year

Year: 1942

Director: George Stevens

Starring: Spencer Tracy and Katharine Hepburn

My Take: This film is Tracy and Hepburn magic. Two reporters, Sam and Tess, fall in love and get married only to have a strained relationship because of how busy Tess is.

#71 Waitress

Year: 2007

Director: Adrienne Shelly

Starring: Keri Russell and Nathan Fillion

My Take: Waitress, an unusual romantic comedy for sure but one nonetheless, tells the quirky story of a waitress hoping to win a pie baking contest so she can leave her husband with the money. Along the way, she has an affair with the town’s new Doctor.

#72 It Could Happen To You

Year: 1994

Director: Andrew Bergman

Starring: Nicolas Cage, Rosie Perez and Bridget Fonda

My Take: An enjoyable romantic comedy that embraces the genre’s fairy tale roots as two characters share a lottery ticket and fall in love.

#73 Miss Pettigrew Lives For A Day

Year: 2008

Director: Bharat Nalluri 

Starring: Frances McDormand, Amy Adams, Ciaran Hinds and Lee Pace

My Take: Part romantic comedy, part period drama, this depression era comedy of errors tells the entertaining story of a broke governess who suddenly finds herself working for a singer for a day as her social secretary, only to fall in love with a wealthy gentleman.

#74 The Abduction Club

Year: 2002

Director: Stefan Schwartz

Starring: Sophia Myles, Matthew Rhys, Alice Evans and Daniel Lapaine

My Take: Based on true events from history, this very funny (and very romantic) period drama tells the story of Irish noblemen (younger sons from wealthy families that will not inherit money, titles or an estate) who abduct wealthy women so they can marry into money. You can imagine what happens when two young men abduct two women with a mind of their own.

#75 Shakespeare in Love

Year: 1998

Director: John Madden

Starring: Gwyneth Paltrow and Joseph Fiennes

My Take: This Oscar winning romantic comedy tells the story of Shakespeare who falls in love with a woman who longs to become an actress (even though it’s forbidden for women to perform). This is a wonderful film from start to finish.

#76 Lars and the Real Girl

Year: 2007

Director: Craig Gillespie

Starring: Ryan Gosling and Kelli Garner

My Take: A love triangle between a young, eccentric man, a lifelike doll and a real girl. Bizarre, yet beautiful, this romantic comedy tries something new and pulls it off.

#77 The Proposal

Year: 2009

Director: Anne Fletcher

Starring: Sandra Bullock and Ryan Reynolds

My Take: Proving once again that no one does romantic comedies better than Sandra Bullock, this film is funny and unafraid to be faithful to the genre.

#78 It’s Complicated

Year: 2009

Director: Nancy Meyers

Starring: Meryl Streep, Alec Baldwin and Steve Martin

My Take: A “complicated” romantic comedy about two exes who carry on an affair is incredibly funny and ends in just the right way!

#79 Bringing up Baby

Year: 1938

Director: Howard Hawks

Starring: Cary Grant and Katharine Hepburn

My Take: A very entertaining romantic comedy about a paleontologist who crosses paths with an heiress and her pet leopard who makes his life difficult.

#80 Knight and Day

Year: 2010

Director: James Mangold

Starring: Cameron Diaz and Tom Cruise

My Take: Better than people give this film credit for, this action/romantic comedy parody tells the story of June who finds herself falling in love with a mysterious secret agent as dead bodies keep piling up and they go on the run to escape the “bad guys” trying to kill them. The scene on the plane is one of the funniest scenes I’ve seen in a movie and I can watch it on repeat! If you haven’t seen the film, I recommend giving it a chance.

#81 Shop around the Corner

Year: 1940

Director: Ernst Lubitsch 

Starring: Margaret Sullivan and Jimmy Stewart

My Take: This film would later work as the influence behind You’ve Got Mail, but it’s great on its own merit. It’s the story of two co-workers who can’t stand each other, but fall in love as pen pals.

#82 The Decoy Bride

Year: 2011

Director: Sheree Folkson

Starring: David Tennant and Kelly Macdonald

My Take: In a small Scottish town, an aspiring author without any money becomes the decoy bride for a famous actress to throw the paparazzi off the wedding’s trail. In the process, she and the famous groom fall in love. Basically, who doesn’t love David Tennant? If you don’t know who he is, watch this and Doctor Who and you’ll know what I mean!

#83 The Artist

Year: 2011

Director: Michel Hazanavicius 

Starring: Jean Dujardin and Berenice Bejo

My Take: The Artist won Best Picture at the Oscars and deservedly so. While being a silent film, it’s also part romantic comedy (though the film does get darker later in the movie) and tells the story of a famous silent movie star who falls in love with a dancer (who is also an aspiring actress). But as the talkies become the new thing and Peppy (his love) becomes an overnight success, problems follow.

#84 Warm Bodies

Year: 2013

Director: Jonathan Levine

Starring: Nicholas Hoult and Teresa Palmer

My Take: Bending genres, this zombie flick is more romantic comedy than anything else as R (a zombie) rescues a girl and begins to feel human again.

#85 The African Queen

Year: 1951

Director: John Huston

Starring: Humphrey Bogart and Katharine Hepburn

My Take: Adventure, romance and comedy, this film has it all. Opposites attract in this fantastic movie with an Oscar winning performance from Humphrey Bogart.

#86 Enchanted

Year: 2007

Director: Kevin Lima

Starring: Amy Adams and Patrick Dempsey

My Take: A princess from a musical, animated land is sent by an evil witch to the modern, real world. This romantic comedy has our princess then fall in love with a lawyer who helps her. It’s funny and romantic with some great twists and turns.

#87 Mamma Mia

Year: 2008

Director: Phyllida Lloyd

Starring: Meryl Streep, Pierce Brosnan, Colin Firth, Stellan Skarsgard, Amanda Seyfried and Dominic Cooper

My Take: A musical that can be watched over and over, this romantic comedy tells the story of Sophie who invites the three men who could be her father to her wedding, unbeknownst to her mother Donna. What follows is a rekindling of an old romance between Donna and Sam (Pierce Brosnan) with many comedic situations on the side.

#88 Hairspray

Year: 2007

Director: Adam Shankman

Starring: Zac Efron and Nikki Blonsky

My Take: This musical romantic comedy is about Tracy, an overweight teenager who dreams of dancing on The Corny Collins Show (while also fighting for integration on the show). Meanwhile, she falls for the lead dancer of the show, Link Larkin.

#89 Legally Blonde

Year: 2001

Director: Robert Luketic

Starring: Reese Witherspoon, Matt Davis and Luke Wilson

My Take: A memorable romantic comedy with girl power has Reese Witherspoon at her best. A “ditzy” blonde goes to Harvard Law School to win her boyfriend back, only to find out he’s a heartless cad. She then falls for another lawyer who sees her for who she really is.

#90 Last Holiday

Year: 2006

Director: Wayne Wang

Starring: Queen Latifah and LL Cool J

My Take: This underrated romantic comedy is pure, light-hearted fun. Georgia, a shy department store clerk who dreams of being a chef and marrying her co-worker Sean, discovers she’s dying. She then takes all of her money and goes on an expensive holiday deciding to finally “live” with the little time she has left.

#91 Scoop

Year: 2006

Director: Woody Allen

Starring: Scarlett Johansson, Hugh Jackman and Woody Allen

My Take: A blend of many different genres, the film follows the classic structure of a romantic comedy – while also being its exact opposite. This supernatural mystery (and very satirical) romantic comedy will make you laugh while also causing you to question whether or not the leading man is a serial killer.

#92 Not Another Happy Ending

Year: 2013

Director: David Solomons

Starring: Karen Gillan and Stanley Weber

My Take: A traditional romantic comedy of an author and her publisher/editor who have a love/hate relationship. While there’s nothing particularly new here, the two leads shine in this little known independent film that is very cute, very funny and very romantic.

#93 Casanova

Year: 2005

Director: Lasse Hallstrom

Starring: Heath Ledger and Sienna Miller

My Take: This hilarious romantic comedy tells the story of Casanova and how he falls in love with an independent and moral young woman who shows him what real love is.

#94 Bride & Prejudice

Year: 2004

Director: Gurinder Chadha

Starring: Aishwarya Rai Bachchan and Martin Henderson

My Take: Basically it’s Jane Austen’s Pride and Prejudice with a romantic comedy, Bollywood style twist. This movie is quite fun to watch and fully embraces old-fashioned romance.

#95 Mr. and Mrs. Smith

Year: 2005

Director: Simon Kinberg

Starring: Brad Pitt and Angelina Jolie

My Take: Part action, this romantic comedy of two married assassins (who don’t know of each other’s job) learn the truth when they’re hired to kill each other.

#96 Magic in the Moonlight

Year: 2014

Director: Woody Allen

Starring: Colin Firth and Emma Stone

My Take: While there is an uncomfortable age difference between the actors, this period romantic comedy is nonetheless hilarious with Colin Firth at his Mr. Darcy best.

#97 Down With Love

Year: 2003

Director: Peyton Reed

Starring: Ewan McGregor and Renee Zellweger

My Take: A satirical romantic comedy that pays homage to Rock Hudson/Doris Day classics. It’s very funny with a surprise ending that made the whole movie worth it.

#98 Brown Sugar

Year: 2002

Director: Rich Famuyiwa 

Starring: Sanaa Lathan and Taye Diggs

My Take: An enjoyable romantic comedy about two friends who have known each other since childhood who finally fall in love.

#99 Northanger Abbey

Year: 2007

Director: Jon Jones

Starring: Felicity Jones and JJ Feild

My Take: While a TV movie, this Jane Austen adaptation goes into romantic comedy territory with charming performances and wonderfully romantic scenes.

#100 The Englishman Who Went Up a Hill But Came Down a Mountain

Year: 1995

Director: Christopher Monger

Starring: Hugh Grant and Tara Fitzgerald

My Take: An English cartographer comes to a small, Welsh village only to give them the bad news that their “mountain” is really only a hill. But the townspeople don’t give up and work to prove that their hill is in fact a mountain. Meanwhile, the cartographer falls in love with a woman from the village. This is a heartwarming romantic comedy.

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Stay tuned when I share part two of the 100 best romantic comedies of all time. For now, what are your favorite romantic comedies?

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