Step 6: Draw two lines below the Riddler's head as guides for the neck. The line on the left should be short because most of that side will be hidden behind the head.
Step 7: On the top part of the Riddler's head, about halfway between the eyes and the top of the circle, draw a long horizontal line as a guide for the brim of his hat. The ends of the line should curve up slightly.
Step 8: Draw a tall arc above the head as a guide for the top of the Riddler's hat. The end of the line on the right should rest on top of the ear, and the end on the left should meet the brim of the hat. The height of the hat is about the distance between the brim of the hat and the bottom of the circle.
Step 9: That’s it for the initial sketch! You have the basic shape of the Riddler cartoon character from Batman: The Animated Series. Now go in and tighten your Riddler drawing. From this point on, press harder with your pencil in order to get darker lines and a more defined sketch.
Step 10: Tighten the shape of the Riddler's eyes as you make the lines darker. The eyes come to a sharper point at the end closer to the vertical construction line.