It was a big job taking over 20 broken hours to complete (less than the damn Keith Richards one because I made sure I had a decent reference this time!). It was done digitally using a Wacom Intuos 3 and photoshop. I use low opacity and flow to build up the texture using a rough round bristle brush.
Anywho here's how it all transpired...

The base was a quick sketch done manually, after a couple of aborted digital attempts pissed me off.

Step one was, as always just to lay down a new layer over the base and fill it with a mid tone with some texture, then drop it's opacity, add another layer and start blocking in colour.

As you can see I also added a cigar and hand from another reference, and am adding more detail to the caricature, but still essentially blocking it in.

After the general tones and shadows are are done I start around the eyes and work my way out, I only managed one eye this day, but it looked alright so I gave myself the rest of the night off.




Finishining off the eyebrows (a pleasure to do Sir Winston) and am just refining the remaining areas.


The reference for the hand wasn't that great so it was a fair bit of interpretation and staring at my own hand. I also scaled it down to make sure that the face was the main focus. added some more background texture and we're done!