Legendairy (credits to my friend Edward Feng for this really dumb pun)
Because he plays with pooh.
Because he only had one pupil! The joke is that I have no friends
Because it **soots** him. Credit: Curious: The Tourist Guide
He finishes her drink EDIT: Apparently this is Conan's joke, so all credit goes to him. I just heard it from a friend of mine and I had no idea.
Legendairy From my young daughter