First I did some quick rough sketches and a concept for the final design once I found an orientation I liked.
In Illustrator I made a vector version of the design, and added a little more to make it more interesting, (drip from the eyes, nose and mouth). Once I finished the main design based on the initial concept (the left at the top), I tooled around looking at different colors and gradients to see what worked best.
Overall I think with the vector designs the red gradient seemed to look the best. I converted the file to a psd to see if some touch up in Photoshop would be worthwhile.
Once in Photoshop I applied a pavement texture from one of the free texture sites online and did some brushwork to add some detail. I think this could still use a bit of work but I'm happy where the design is. Too much more fiddling might be a bit much and I would hate to guild the lily, or skull I guess. Oftentimes with a design it's good to know where to stop before overdoing it.
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