Draw a circle for the top of Gollum's head and then a triangular sort of shape underneath it draw a line from the top of his head down to his chin. This line should not be straight but should follow the contours of his head. Then do a line for where his eyes will go and one for his mouth and nose also.
Draw in his eyes and the shape of his nose as well as his mouth and teeth. Sketch in his pointy ears. Start defining some of the major shapes on his face such as his jaw. Draw in his torso.
Start shading his head AFTER you think you have the sketch right. His eyes are bright but shaded dark around his eyelids. I erased my original guidelines here but they can help you shade if you don't erase them because it will help you draw 3D. I also drew some guidelines for his arms.
Keep shading his head and neck. Concentrate on his wrinkles and the contours of his face.
Draw in his hair and keep shading his body. Draw the specks he has on his skin, especially around his mouth. He's starting to look quite handsome now.
Shade his body so you can see his ribs and bones on his neck and such. I used a sort of crosshatching shading for the skin on his arms.
Finish shading his legs. Blend the skin tones where you should. Redefine highlights with a kneaded eraser and darken the tones you lost by smudging. Make any finishing touches you want and add a background if you want.
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