Played a little with Crazy Talk, it's a program like the PhotoSpeak app. Makes a person's face in a photo move.
So what did I try first with it?
Go all nerdy and make a photo of Yukirin sing, of course.
i'm helpless.The clip is pretty much already like that just by importing the pic and song.
Just tweaked the face points, removed the extra lip movement (since it treats music as talking), set an emotion (like happy or angry), and add a little blinking.
Course, it could all be tweaked and timed right to look a little more natural. And I'm pretty surprised how much extra stuff I could edit in it.
So it's a good timewaster just like PhotoSpeak, but with more options.