According to Slate writer, and recent New Yorker cartoon caption contest winner, Patrick House, most people who look at the contest winners conclude they are, in fact, funnier. Says House,
You’re right. But that doesn’t mean you could’ve won the caption contest…You are not trying to submit the funniest caption; you are trying to win.
The key to victory: know your audience. And by audience he is mostly referring to the cartoon caption gate keeper who looks at all the captions (which has to be a lot like getting stuck at a family dinner with your unfunny uncle) and decides which entries will make it to the second round. Also, House advises, stop trying to be funny.
Is it too funny? Will it make anyone laugh out loud? If so, throw it out and work on a less funny one.
After that it’s just about having more friends than the next guy to vote for you online, and voila! fame and fortune await.