Sleepy grew up in a castle in the middle of Fried-Land where a magic cookie wasp stung him and turned his eyes into cookies and cream visions so he can see what is the next move of his opponent.
The legend tells that he was beheaded while sleeping, some tendies and cocks think that it was during the battle of Friederdolf he got a cannon ball to his head but did die because of the cookie wasp sting that made him immortal.
So now he walks around with his head floating over his shoulders. He sometimes stops to tell people the future and most times it is related to how they will die. So everyone keeps a safe distance.
Sleepy doesn't have many friends but the dragon that sleeps in his castle takes him around the kingdom every now and then.