America’s funniest romantic comedies, by decade

Today, I heard the sad news that Nora Ephron, screenwriter for Sleepless in Seattle passed away.

I thought a fitting tribute would be to list our favorite American romantic comedies from each decade.

1920s.  Steamboat Bill Junior.
  Two steamboat men have a rivalry, Bill’s dad and the girlfriend’s dad.  Bill’s dad is a real tough guy, and he hates the rich guy with the big boat.  Bill’s dad’s successful rival hates Bill’s dad, seeing him as a low life.  So, Bill Jr. and his girlfriend aren’t allowed to see each other.  Worse than that, Bill Jr. is an embarrassment to his father, as a wimpy college type.  Can Bill save his father, see the girl, and win her father over?
1930s. Bringing up Baby.
Normally, having a big cat on the loose might seem like a cheap gimmick.  Katherine Hepburn was in a lot of great films, and the rest of the cast wasn’t so bad either.  What really made this for me, though, is how believable the characters were in such a weird situation.  And the movie doesn’t age.
1940s.  The Philadelphia story.
This is a tough decade, but I’ll have to go with this one about a woman who has a choice between being a “newspaper man” and a new comfortable life married to some big-shot.  Well, she already made that choice, but her old boyfriend (and an escape convict) have other ideas.
1950s. Marty.
It’s such a simple story about a World War II veteran who always gave his life to other but never got married.  Marty’s convinced it’s because he’s ugly.  He became a butcher, where his customers criticize him for being single and now he finally meets a woman, a teacher who underestimates herself.  Suddenly, all his friends and family try to stop him from gaining success in life for their own selfish ends.
1960s. The Apartment
During this decade, movies started getting a little weird, but it started out alright.  The musical was in high gear.  Jack Lemmon, however, deserves some kind of mention, somewhere, so here it goes.  And who else but Wilder and Diamond can turn statistics like the population of New York into a gag and a piece of character exposition?
1970s. Sleeper.
A clueless man goes ahead in time to find the rest of the world has grown even duller than he is.  The people are so hungry for wisdom, so enamored with leadership, that they copy his every moronic whim.  The plot has been copied hundreds of times, but Woody Allen actually makes it funny. Others to watch: the The Aristocats.
1980s. Brewsters Millions.
Not all professional baseball players are rich, and Monty Brewster is pretty much destitute.   Suddenly, opportunity knocks, and he has to waste 30 million dollars without giving it away before the deadline in order to inherit even more.  If he fails, he ends up dirt poor again.  (Too bad for him that “social media” didn’t exist back then, the modern Internet is a quick an easy way to waste a fortune.)  He’s followed along by a lawyer who grows on him, but unfortunately he can’t tell her the full story.  While he wants to impress her, and she wants to help him, it looks like it just won’t work out.
1990s. My Best Friend’s Wedding
Sorry Nora, but as funny as you were, some people were funnier.  Maybe if you had a chance to bring together the comic genius of Julia Roberts and Cameroz Diaz.  This was a wonderful tale of the jealous old girlfriend trying to mess things up and failing, but becoming friends with her rival in the process. 
And the first draft of the script is available online, it may seem lackluster compared to the final with all the constant karaoke scores, but it shows that a strong plot can come before the biggest laughs are in place.
2000s. Napoleon Dynamite.
No, this is not your typical romantic comedy, but that wasn’t your typical decade.  From El Mariachi in the 1990s, Americans were realising that genres other than horror and exploitation could succeed with a low budget.  It didn’t have much of a plot, and unfortunately most of those involved have yet to make an equally entertaining film, but at least Napoleon Dynamite was funny.
2010’s This decade’s not over yet.  (perhaps Tangled?)

Have a different list? Let’s hear it.