Awhile back, Greg posted an article by Sally Hogshead with the simple statistical reality that you have to write about 100 headlines to get a good one. And while creativity by committee can be a frustrating and deadly process, if you have a concept, it sometimes helps to have several writers plugging away at headlines, just to generate the volume.
Here's an example I found entertaining and relevant to what we do. It's a story from This American Life about the process they go through at The Onion to create their fantastic headlines.