A couple things -
When they switched to reader-judging of the contests, my disdain for humanity increased several fold (the dumb things people think are funny, the insanely long captions, the not getting the part of who is actually supposed to be talking - it goes on and on).
And, I like to go here: The New Yorker Cartoon Caption Contest Dataset to torture myself by looking at this caption disaster porn. And, I’ll also check to see how far down my caption is in the list if I submitted one (I think the highest I ever got was top 20 or 30).