There are classic romantic comedies, dramatic romantic comedies, thoughtful romantic comedies, and guilty pleasure romantic comedies. Whatever their style, the best romantic comedy films have characters that we love, love to laugh with, and hope to see live happily ever after. While there are many great romantic comedies, these are the movies that I consider the top ten best romantic comedy films of all time.
10. 10 Things I Hate About You (1999)
“Romantic? Hemingway? He was an abusive, alcoholic misogynist who squandered half of his life hanging around Picasso trying to nail his leftovers.”
There’s plenty to love about this romantic film starring Julia Stiles and the late Heath Ledger. Loosely based on Shakespeare’s Taming of the Shrew, 10 Things I Hate About You takes the bard’s story to a 20th century high school. Stiles plays the uber-intelligent, strong-willed Kat Stratford, who feels the whole teen scene is beneath her. Ledger swoops in as bad-boy Australian transplant Patrick Verona, who seems utterly–and infuriatingly–charmed by her wicked shrew act.
Stiles and Ledger are fiery and fun to watch, and there are great supporting cast moments from the likes of Joseph Gordon-Levitt and Allison Janney. Larry Miller, playing Daddy Stratford, almost steals the movie with his hilariously disturbing lectures of how dating leads to teen pregnancy–as well as a memorable scene involving exercise equipment.
9. Bridget Jones’s Diary (2001)
“I realize that when I met you at the turkey curry buffet, I was unforgivably rude, and wearing a reindeer jumper.”
Renee Zellweger tends to be a bit of a caricature these days, but Bridget Jones’s Diary is one of her best and most charming roles. Who can help cheering for the slightly overweight single girl in her 30s who’s attracted to bad boys, can’t shake her bad habits, and suffers every Christmas from bad clothing forced on her by her mother? And of course that tall, proud Darcy–played by Pride and Prejudice hunk himself Colin Firth–is always at every social function, wearing equally bad holiday sweaters.
Throw in delightfully devilish Hugh Grant as Bridget’s boss, and sexual harassment in the workplace never looked so good. As Stephanie Zacharek wrote in Salon, “The script is teasingly, pleasingly raunchy in places.” Firth, Zellweger, and Grant make a delightful love triangle, the dialogue is hilarious, the plot nutty, and there’s nothing better than seeing Grant and Firth fighting awkwardly in the street.
8. You’ve Got Mail (1998)
“Brinkley is my dog. He loves the streets of New York as much as I do, although he likes to eat bits of pizza and bagels off the sidewalk and I prefer to buy them.”
Based on The Shop Around the Corner (1940), You’ve Got Mail turns letters of correspondence into thoughtfully typed emails. Meg Ryan plays a lady with the little book shop that gets overshadowed by the giant new bookstore chain in town–run by Tom Hanks’ character. The two seem destined for mutual hatred, except for the fact that they’re already anonymous email buddies who share their innermost secrets on a daily basis.
The film is an enjoyable romantic comedy, but it also has substance. It is often thoughtful and poignant, tackling issues of self, destiny, and the questions of big vs. small business–from both sides. A movie that includes plenty of voice-over reading of emails could be dire, but the endless charm of Meg Ryan and Tom Hanks makes it golden. Supporting players help round out the film, especially the delightful Greg Kinnear who manages to be sweet and a little smarmy at the same time.
7. About a Boy (2002)
“Me, I didn’t mean anything. About anything, to anyone. And I knew that guaranteed me a long, depression-free life.”
Critics were impressed at the Hugh Grant that emerged in coming-of-age tale About a Boy. A romantic comedy staple, Grant has made a career of self-effacing, nervous and stuttery charmers. Here Grant plays a spoiled, idle man who has nothing more serious to do in a day than get his hair cut or buy CDs. Unlike the usual romantic comedy hero, he’s selfish, shallow, and not all that nice to anyone–including family.
That is, until he meets a geeky kid, the kid’s unstable mother, and a lovely and intelligent woman he wants to be a better person for. Nicholas Hoult is pitch-perfect, his character a real kid that bears no resemblance to the nerdy stereotypes of other films. Weisz and Toni Colette are stellar in their roles as interesting and complicated women, contributing greatly to a quality story that has laughs but also a lot of heart. Of the film’s central relationship between man-child and child, Jeremy Medina at Paste Magazine writes “Grant’s relationship with the boy is tender and thoughtful, much like the film itself.”
6. Pillow Talk (1959)
“At least my problems can be solved in one bedroom. You couldn’t solve yours in a thousand!”
We tend to think of 1959 in Pleasantville terms, not in sex comedy terms, but that’s what Pillow Talk was considered when it was released. This Rock Hudson and Doris Day classic features the two performers as characters sharing a party line–she the sensible career girl, he the womanizing song writer. Their arguments over the phone range from hostile to flirtatious to downright suggestive, and the clever use of split screen elements adds to the fun. Or as the original 1959 review in The New York Times puts it: “…this fun is transmitted to the audience in an easy and generous flow of ingeniously graphic situations and nimble repartee.”
This entertaining vocal dance runs parallel to the pair’s real life meeting, where he assumes another identity to woo her. Throw in Tony Randall as interested suitor and best friend, and you’ve got plenty to work with for romance, suspense, and comedy. Once you’ve seen the original, you can see the modern update in the form of Ewan McGregor and Renee Zellweger in romantic comedy Down With Love.
5. Moonstruck (1987)
“The snowflakes are perfect. The stars are perfect. Not us. Not us! We are here to ruin ourselves and to break our hearts and love the wrong people and die.”
Cher and Olympia Dukakis won Oscars for the insane and beautiful Moonstruck, a film about an Italian-American family and their individual experiences with love, marriage, and sex. There are affairs. There are family squabbles. There is a full moon.
Nicholas Cage and Cher are both unorthodox leading actors, and their pairing here is absolute magic. He talks crazy, she slaps him across the face, he carries her to bed. There is passion and angst in large heaping amounts. The film hits humorous and dramatic notes in a variety of ways, from broad comedy to little quiet moments of truth–like the blunt conversation between a disappointed wife and a womanizing professor. The cast is overflowing with talent, and Moonstruck maintains its appeal after many years and multiple viewings.
4. His Girl Friday (1940)
“He’s got a lot of charm.”
“Well, he comes by it naturally–his grandfather was a snake.”
His Girl Friday is fast. Even modern moviegoers who are used to frenetically-paced action flicks with flying fists and exploding cars will be shocked at the speed of this film. Set in a newspaper office full of cynical and wise-cracking reporters, His Girl Friday gets three more lines of dialogue in while you’re still processing the first. Cary Grant is all devilish charm, and Rosalind Russell more than matches his wit and sass.
As clever lines go zipping back and forth, there’s a love triangle to consider as well as a murderer on the loose. The dialogue meshes with quick-footed action and danger that should keep even the most jaded moviegoer on their toes. AMC’s Filmsite describes His Girl Friday as “speedy and hysterically funny… a modern-style screwball comedy, and one of the best examples of its kind in film history.”
3. Music and Lyrics (2007)
“That’s wonderfully sensitive… especially from a man who wears such tight pants.”
“It forces all the blood to my heart.”
If you remember the 80s, you won’t be able to stop laughing from the moment Music and Lyrics begins–with a Wham!-like video starring a “young” Hugh Grant. With shout-outs to all that is bad and beautiful about the 80s, and wonderfully catchy pop tunes you’ll be singing long after, Music and Lyrics hits all the right nostalgia notes while comparing it to the reality of today’s music biz.
The film follows Alex Fletcher (Grant), once a teen idol and now a has-been performing at Knott’s Berry Farm and tractor shows. Things seem set to change, however, when his agent (Brad Garrett) informs him that pop princess Cora Corman (Haley Bennett) wants him to write a song for her. Enter substitute plant-waterer Sophie Fisher (Drew Barrymore), a once-aspiring writer who scrapped her dreams after a devastating relationship with a backstabbing professor. These two damaged souls team up, and romance and hilarity ensues.
The dialogue is clever and quick, with Grant’s trademark mumbled zingers often continuing even as the scene is ending. Music and Lyrics requires multiple viewings, as laughter often covers up these little asides. Barrymore is her charming, adorable self, Grant and Garrett have a wonderful comedic chemistry, and Kristen Johnston steals every scene she’s in.
2. When Harry Met Sally (1989)
“I’ll have what she’s having.”
Film critic Roger Ebert describes When Harry Met Sally as being “…about two people who could be characters in a Woody Allen movie, if they weren’t so sunny, and about how it takes them 12 years to fall in love.” Meg Ryan and Billy Crystal are the most unlikely couple, but somehow it works brilliantly, and it’s incredibly entertaining to listen to them banter and watch Sally continually wrinkle her nose in distaste and shoo away the sarcastic and obnoxious Harry.
Sure there’s the iconic fake orgasm scene, but When Harry Met Sally is full of fantastically quotable lines like “You mean Mr. Zero knew before you knew?” and “Oh, but ‘Baby Fish Mouth’ is sweeping the nation?” Every moment of Harry and Sally’s lifelong friendship is interesting, or funny, or devastating, or triumphant. Carrie Fisher and the late Bruno Kirby provide perfect comedic support as the couple’s best friends, and the result is a warm and intelligent romantic comedy that so few of its followers have ever lived up to.
1. While You Were Sleeping (1995)
“You don’t have to walk me home.”
“You block the wind.”
While You Were Sleeping is a hot cup of cocoa after a day of shoveling a foot of snow. The characters of the film, which is set in Chicago, would understand that metaphor. Though it’s a scre wball comedy, with a love triangle that includes a stranger in a coma, While You Were Sleeping is a warm, sweet, and satisfying romantic comedy. Sandra Bullock and Bill Pullman are immensely likable, and believable as working class folk searching for their slice of happiness. They also sizzle with sexual tension and true depth of feeling–a combination not often found in an often superficial genre.
The supporting cast of wacky family members, including Peter Boyle and Glynis Johns, fill the screen with life and humor. Jason Bernard is hilariously blunt as Lucy’s exasperated boss, and Michael Rispoli is perfect as the amorous and mildly deviant neighbor Joe Fusco, Jr. Any girl who’s ever wished for a better life and a Prince Charming by her side–but has a cynical streak that dismisses such sexist fantasies–will fall in love with While You Were Sleeping. It’s not just about getting the guy, it’s about being honest with yourself and getting more out of your life. Which isn’t a bad message for a rom-com.
“10 Things I Hate About You”, “Bridget Jones’s Diary”, “You’ve Got Mail”, “About a Boy”, “Pillow Talk”, “Moonstruck”, “His Girl Friday”, “Music and Lyrics”, “When Harry Met Sally”, “While You Were Sleeping”. Internet Movie Database.
Crowther, Bosley. “Pillow Talk”. The New York Times.
Dirks, Tim. “His Girl Friday.” Filmsite.org.
Ebert, Roger. “When Harry Met Sally.” Chicago Sun-Times.
Medina, Jeremy. “The 17 Best Romantic Comedies This Decade”. Paste Magazine.Zacharek, Stephanie. “Bridget Jones’s Diary”. Salon.