I find it both slightly ridiculous and completely endearing that I have to wish goodnight to every single toy Jake chooses to sleep with.
Tedd E. Bear, Rainbow Dash from my little pony fame, (who Jake insists: despite my assurances that she is female; "No, Mommy, Rainbow Dash is a boy pony! He's BLUE and he can FLY!!!") Wolfy (pretty obvious what he is...) Buzz Lightyear, and occasionally, Optimus Prime... When they wish me a goodnight in various squeaky to growly voices. *sighs* What a production!
I've tried culling the herd, but god forbid he might end up missing one or two of his buddies at night. Silly kiddo.