A headline's goal should be to capture the tone and meaning of the story.
This headline from Sunday's Washington Post does neither: Johnnie-Mid seminar breaks social impasse in Annapolis. Huh? Based on that headline alone, that story could have been about a million different things. My best guess that was I was about to learn about the middle parts of a guy named Johnnie who held a miraculous summit to overcome the austere social rules governing Annapolis.
As it turns out, the story was about none of those things — thankfully. I read on to discover a delightful tradition, where students from St. John's College and the Naval Academy — two polar opposite schools that sit blocks apart — gather for an annual summit to discuss a book. This year they read Anton Checkov's "Gooseberries."
As for a good headline, I like this one from The (Baltimore) Sun: "Late-inning collapse dooms Orioles in 5-2 loss" It's search engine friendly and tells you precisely what's happening in the story.
Finally, this headline, which I found on a journalism web site is truly ugly: "Governor swears in legislature."