This was done as the key art for Jack Brooks: Monster Slayer. It's a combination of photo manipulation and painting in Photoshop. The title treatment was made in Illustrator. The tentacles are illustrated, as is the head hanging in the background.

The rest is photo manipulation, with the exception of Jack's face, which is 50% photo and 50% painted since the model I used in the photo shoot didn't look like the actor from the movie. I kept the models eyes and mouth, photoshopped in the hat, hair and ears, then painted a new nose, beard, neck and eyebrows.

Hope you like it, and thanks for looking!