When is something funny enough? That’s a little hard to say since every example is different and every case is subjective. But as a general rule, whenever I write a joke I ask myself two questions.
Is it funny?
What would be funnier?
Just getting a yes on the first question is no easy task. And by funny I mean FUNNY. Not wry, not amusing, not lol, not smiley face, but something that will make people actually laugh. And not just people – strangers. It’s hard. It’s why they used to pay the big money.
So when you feel your joke has passed the rigorous mirth test it’s tempting to take a moment, pat yourself on the back for being a comic genius, and move on to the next triumph That’s what most comedy writers do.
Don’t be one of them. Ask the second question. How can you make the joke funnier? What’s a more offbeat reference that achieves the same result? What’s fresher? Is there a better set up? Is the wording just perfect? Or is there just a better line altogether?
Small example of a joke just to give you a sense of my thought process. When 
Manny Ramirez was suspended for violating baseball’s drug policy I was asked if I was surprised. My first thought was, “At this point I wouldn’t be surprised if Mother Teresa was a dope dealer.” The incongruity of Mother Teresa selling drugs seemed funny. But “is there something better than dope dealer? What I came up with is this: “I wouldn’t be surprised if Mother Teresa was a gun runner.” That seemed to suggest a funnier image, Mother Teresa haggling with terrorists over AK-47’s.
At some point of course you've got to land on a joke and go with it otherwise you can spend the next fifty years trying to get Jess out of a room. But don't just automatically settle for the first thing you come up with. That sounds obvious but you'd be surprised how many writers do.
A better example comes from THE HANGOVER. How many bachelor party gone-bad-in-Vegas screenplays do you think there’ve been? A thousand? Ten? Four idiots getting shitfaced and in trouble in sin city is comic gold. But I bet none of those scripts had tigers, chickens, missing babies, and Mike Tyson. Okay, well most of them didn’t have Mike Tyson. But you catch my drift. Reach.
There’s an expression in the writing room – “Can we beat this joke?” Don’t settle. ESPECIALLY if you’re writing a spec script.
Eventually you’ll train yourself to automatically think that second question. It could be the subtle difference between good and “you’re hired”.
This was a re-post from the last decade. But revised.