What Did You Call Me?

What? You thought Legolas was the last one? Gollum did aid Frodo in his quest to destroy the Ring, so technically he was  part of the Fellowship.

Taken from the scene: "The Passage of the Marshes" in The Lord of the Rings: The Two Towers.

Probably the closest Smeagol ever comes to recovery is when Frodo calls him by name and treats him like the person he used to be, rather than the creature he had become.

  I find it strange and rather sad that most pieces of art I've seen depicting Gollum always focus on the despicable, little gangrel creature. I suppose most people don't care to look beyond the emaciated appearance, raw-fish-eating and guttural utterances of "my precious" to see the person beneath. For my part I wanted to capture the heart and soul of Smeagol, to depict the profound, abiding sadness of this most unfortunate character.
  Inspite of all that, though, I had tremendous fun working on this one. In all honesty, after "Rainfall and Short Jokes" I didn't think there was much room for improvement, but it seems I've proven myself wrong. This one easily tops the other nine, and I would say that as the culmination of eight months of hard work and daring experimentation, the whole endeavor was well worth every ounce of frustration, trial, and error.

Drawn and painted on a Nintendo DSi XL in Art Academy: Second Semester.

See also:
Process video: [link](you really should watch this)