This ran with an article that was published a couple of months after the attack on the World Trade Center in New York, and the headline was "Is it OK to laugh now?" or something like that. (Edit: After a little searching I can say that's exactly what it was called, and this was the cover to the entertainment tabloid, not an illustration on the regular news page.)
It was fun to paint, but I remember this assignment as my first huge frustration with an editor. The idea I pitched was a crowd of clowns-- just like this layout, more or less -- but the characters would all be sad clowns. They would have frowns, their heads bowed, their eyes shut; very serious and dignified and respectful for a bunch of clowns.
But one of them would have a smile, and this clown would be looking slyly at one of the somber clowns next to him. And in his hand? A pie! Ready to go. It is time! Ha!
I was really excited about it. However, the editor saw one of my other thumbnails, and it looked like this illustration: People, still sad and hurt, cautiously or angrily eying the clown in their midst.
The editor insisted that this was the better idea. I said that it was not as satisfying conceptually or visually as the all-clown idea. Then, the editor insisted that I was wrong. I said I didn't think so. Then, the editor commanded that I was wrong. I relented. Insert heavy sigh of regret here.
I was still new on the job, I still had to ask questions all of the time about how things worked. My confidence in my instincts was strong but I didn't have the weight of experience behind me. I gave in out of respect for the editor even though I knew it was the lesser of the two concepts.
Oh, well. Just another lesson about how you shouldn't EVER show anyone an idea you don't like -- particularly when working with a client or an editor -- because that's the idea they will like best. Every. Time.
The faces in the crowd I invented or found on the internet, and I did improv portraits from them, changing their expressions to fit the scene. The guy to the right of the clown isn't off the internet. He looks an awful lot like me.