I've seen a lot of comedies, and it can be a great genre. Done right, they are a lot of fun and make you laugh every time you see them. I've seen plenty of these: the witty banter of the Marx Brothers in their various movies (plus Harpo's inevitable slapstick shenanigans), Charlie Chaplin eating his boot in The Gold Rush, Mel Brooks' satires of iconic movies, the hilariously over-convoluted plot of The Big Lebowski, the crazy situations set up by Blake Edwards. The list goes on.
Once in a while, however, I encounter supposed comedies that aren't so hilarious. Even a great comedian can occasionally make mistakes; Jaques Tati made some funny movies like Mr. Hulot's Holiday, but that didn't make Play Time any less dreadful an experience. There are films like Hancock that were fun but didn't get huge laughs, but going even further down, once in a while I encounter a movie that is supposed to be a comedy but just isn't funny at all. The Watch was one I saw on Netflix once that wasn't so much an alien invasion comedy as it was just an overly long and elaborate Costco commercial that never got a single laugh from me.
Same with This is the End, while some unknown viewer a few seats behind me was bursting into laughter every other second and I've repeatedly heard the film hailed as an intelligent comedy, I spent most of it just trying to figure out what exactly was supposed to be funny. Granted, I never had super-high expectations to begin with you know something's wrong when you're invested more with Emma Watson's cameo than the actual plot and spend the whole film just hoping she'll come back.
I still stand by my statement that the film would have been far better if it were just about Emma Watson and the guys it insists on following were just a brief cameo. I also stand by my statement that The World's End was a far better of 2013's "apocalypse comedies" insofar as that film was actually funny, but I've already done a whole other article discussing and comparing those two.
In fact, even more weirdly I have seen the sort of thing done with Emma Watson used to good effect. Sometimes it can be hilarious to have a supporting character who is implied to have a far more interesting story than the protagonists which goes entirely unseen. Shaun of the Dead did this nicely.
After spending the whole film following Shaun's attempt to lead his group to the local pub in an attempt to avoid the zombie apocalypse, he and his girlfriend are now the only ones left and find find themselves in a street filled with zombies. Just when it seems they are done for, the army shows up out of nowhere to save them and it turns out Shaun's friend Yvonne was with them. The implication of course is that whatever she has been up to was probably far more exciting than what we saw with Shaun, but here realizing that fact becomes hilarious, instead of leaving you to wish that the film had instead followed Yvonne.
So as someone who has attempted unsuccessfully to write comedic short stories (and created a few funny stop-motion shorts), I think it would be interesting to try and break down what makes a good comedy. What is it that makes the witty banter between Groucho and Chico Marx so amusing compared to the unfunny conversations between the protagonists of This is the End?
Well, one thing that I suspect has something to do with it is something that is a big part of most good movies, and that is the chemistry between the characters. Many intelligent comedies work because the characters can play off of each other. What makes the Marx Brothers so enjoyable is how they all play off each other. Some of the best moments in their films are just the crazy conversations between Groucho and Chico (the infamous "party in the first part" routine from A Night At the Opera, the "tootsie-fruitsie ice cream" scene from A Day at the Races, or the job interview from Duck Soup being good examples).
Now that's all well and good but having characters who play off of each other effectively is a surprisingly important ingredient to a lot of intelligent comedies, even more contemporary ones. Blake Edwards was a director who could pull this off really well in his films, a good example being Operation Petticoat. In this film, Tony Curtis's portrayal of the reckless vigilante officer would not be complete without Cary Grant playing exactly the opposite. A lot of the fun comes from how Grant is trying to go straight and by the book and how he tries to stay that way even after Curtis not only resorts to property theft on several occasions but also ends up bringing aboard several women and children (remember, the story is set during World War II) that the crew aren't prepared to deal with.
Going into more modern examples, we get this same thing working with good comedy. After all, one of the major driving forces behind The Big Lebowski is the relationship between the Dude and Walter, and a lot of the film's most hilarious scenes are based on the interactions between the characters present. When the scene where the Dude first meets The Big Lebowski, a lot of the humor is based on the obvious contrast between the two of them.
I suspect this may have been a problem with This is the End. I never found the characters there played well off of each other. Nobody had any real contrasts or distinctive quirks or other fun stuff to draw on. In contrast, The World's End had Gary King playing off against several different people. What made Simon Pegg so enjoyable in this role was the contrast to all his friends (especially Nick Frost). King has this very childish attitude, he lives in the past, he can remember all kinds of stuff but can barely keep up with the present. Meanwhile all of his friends have moved on. This provides a good contrast with several of his friends, all of whom have moved on to new lives.
In fact, this really drives much of the Cornetto Trilogy in general. In Hot Fuzz a lot of the humor also comes from the interactions between Simon Pegg and Nick Frost. On the one hand there's the professional cop who is just too darn good at his job, and on the other there's the cop who has no idea what he's doing and bases his ideas of police work off of cheesy action movies. The whole first of the film draws you in with the conversations between this two as Sgt. Angel gets increasingly frustrated with Constable Butterman's questions, but it also sets up the big climax when almost every possible action movie cliche they could find a time to discuss and deconstruct until then is played straight.
So it's hard to say for sure, but if you're a screenwriter, and you want to make a really intelligent, witty, and hilarious comedy, the secret apparently has something to do with having good chemistry between your characters. The key to good humor seems to be connected to having characters who can play off of each other really effectively.
Now I would imagine that it is in fact probably more complicated than that. After all, I have not gone into much detail about silent comedies such as those of Charlie Chaplin or Buster Keaton. Those seem to be based on something entirely different, but perhaps this advice will still be of help in developing your comedic writing.