Favorite Romantic Comedies for Valentine’s Day

A Top Ten list appropriate for February! As I’ve written before, Boots & Backpacks is full of romantic comedy tropes. Which romantic comedies inspired me the most? Why, these!

1. It Happened One Night (1934) IMDB link

Hmm. An opposites-attract road trip? Yeah, I wouldn’t know anything about that. The truth is, Frank Capra’s classic starring Clark Gable and Claudette Colbert is the first and the quintessential Hollywood romantic comedy, with a formula that most subsequent romantic comedies follow. It’s a formula that will feel quite familiar to Pride and Prejudice fans. 1) The two leads meet and usually don’t like each other. 2) They come to know (and love!) each other. 3) Just when we think they might get together, there is a big misunderstanding or revelation that breaks them up, and all hope seems lost. 4) One of them makes a grand romantic gesture and they live Happily Ever After.

Rumor has it that Clark Gable’s carrot-eating-while-talking scene was the inspiration for Bugs Bunny. Can you see it?


2. His Girl Friday (1940) IMDB link

This screwball comedy stars Cary Grant and Rosalind Russell, who give the best banter. In fact, the dialogue is so fast and overlapping that you’ll miss some of it the first time around. I don’t think I need to go into the many charms of Cary Grant as newspaper editor Walter Burns. But I just adore Russell’s Hildy Johnson, the ace reporter accepted and admired by her male peers. Sure, she thinks she wants a “normal” life with a her dull fiancé, but ex-husband Walter knows that if he can manipulate her into staying for one more caper, she’ll change her mind.


3. When Harry Met Sally… (1989) IMDB link

It seems like the deli orgasm scene is all anyone ever talks about. Don’t get me wrong; it’s a great scene, but When Harry Met Sally has much more to offer. We come to know fussy Sally Albright and pessimistic Harry Burns over the course of their years-long friendship. So it really is painful when we think that friendship is over. Luckily it all works out with a New Year’s Eve epiphany.


4. Bringing Up Baby (1938) IMDB link

The screwballiest of the screwball comedies, due in large part to Katherine Hepburn’s scatterbrained Susan (one of the earliest examples of the Manic Pixie Dream Girl). Cary Grant’s David, looking like Clark Kent in his “scientist” glasses, suffers through the various disasters Susan creates in order to keep him from returning to his uptight fiancée. There’s a leopard (two actually), a dog, and a dinosaur bone. Despite everything, it turns out David can’t give Susan anything but love, baby.


5. Bridget Jones’s Diary (2001) IMDB link

I don’t think I need to sell this one, considering my audience! I will say that it has great source material. Helen Fielding’s modern reinterpretation of Pride and Prejudice gives us a heroine a bit less self-possessed than Elizabeth Bennet, but we love her anyway, just as she is.


6. The Philadelphia Story (1940) IMDB link

Any Top 10 list that features Cary Grant three times is a winner, if you ask me! But my favorite part of The Philadelphia Story is Jimmy Stewart as secretly sensitive, struggling writer Macauley Connor. Katherine Hepburn’s socialite Ice Queen Tracy Lord is brought down a peg or two over the course of the movie. But it’s okay. With three suitors, including Cary Grant and Jimmy Stewart, what Ice Queen wouldn’t melt?


7. The Cutting Edge (1992) IMDB link

Speaking of Ice Queens, how about a more literal one? Champion pairs figure skater Kate Moseley can’t keep a partner because she’s a horrible spoiled snob. Desperate for a gold medal at the Olympics, her coach decides to think outside the box. Enter Doug Dorsey, a hockey player from Minnesota whose promising career was sidelined by an eye injury that damaged his peripheral vision. He wants another chance at Olympic glory so badly that he’s willing to learn how to figure skate, not to mention put up with Kate’s attitude. Sparks fly, etc.


8. Clueless (1995) IMDB link

Amy Heckerling brilliantly updates Austen’s Emma, setting it in a Beverly Hills high school. Alicia Silverstone handily carries the film as ultra-popular Cher Horowitz. She takes up match-making for her lonely teachers in order to get better grades; she takes the unhip new girl under her wing: cue makeover montage! The only one who criticizes Cher is her ex-stepbrother Josh, played by a young and dreamy Paul Rudd. Sure, the cell phones look giant now, but is Clueless any less quotable after 20 years? Not even!


9. Pretty Woman (1990) IMDB Link

The movie that made Julia Roberts a superstar can’t be called the most realistic story. But I guess we aren’t looking for realism in romantic comedies. Vivian is a hooker with a heart of gold who manages to catch the interest of lonely yet commitment-phobic corporate shark (and silver fox) Edward Lewis, played by Richard Gere. In My Fair Lady fashion, Vivian is transformed through a series of shopping sprees and etiquette tutorials. But Edward is transformed too, of course, into her knight in shining armor.


10. Blast from the Past (1999) IMDB Link

This underrated comedy boasts Brendan Fraser as a Fish Out of Water in modern-day California. You see, the Webers locked themselves in their fallout shelter during the Cuban Missile Crisis in 1962, believing that the plane crash in their backyard was the feared nuclear strike. Their son Adam was born there. Talk about a nuclear family! After 35 years, Adam ventures to the surface to get supplies, and he hopes he can meet a special girl too. One who isn’t a mutant. He finds Eve (ha ha, get it?), played by Alicia Silverstone. She thinks Adam is a weirdo at first, what with his love for Perry Como and his reaction to seeing the ocean for the first time, but how can she not fall for a hunky guy with perfect table manners? Did I mention he can swing dance like a boss?


I admit that I struggled quite a bit narrowing this list down to ten. Which romantic comedies would make your list?

See more of my Top Ten lists at Culturalist, which is very bad for time management.