So it turns out that Jack does like sleeping, he just doesn't like sleeping in the ways you think he should like sleeping. You can spout your propaganda that most babies like to sleep in their carseats, and you should like it, too, but he's all "I'm my own man and I'll do things my own way and The Man can't tell me what to do or how to be, dig? If I wanna sleep on my Boppy with my head danging off the back until it appears that it will fall off and I will die, it's my right as a human being. And you can try to put me down but I'll fight back and stand up for my people." And then he started singing a little spiritual, but dozed back off again.
Power to the very small people, man.