The Jester is arguably the most well-known of The Wooden Girl's Dolls. As a willing servant, he is allowed a small degree of autonomy. The Jester is known to enjoy playing "games" with his victims - often with cruel consequences if they lose. His existence seems to date back to the late 1800s, though it is unknown if the Jester from those times is the same as the one today, or if the mask is handed down to Dolls inheriting the title. In modern times he is always seen wearing a clown-like mask and a black hoodie.
Jester is also the leader of a group of Dolls known as Misfits. He rarely uses them since he prefers to do things himself, but he does deploy them to aid in his more complex games and "jokes".