Pencils were done in Painter using the 2B pencil tool. I wanted a rough look to the piece.

In Photoshop I used the pencil tool to create an outline on the whole piece, then used the paintbucket tool (anti-alias off) to fill in the empty area. This can be done with Painter too, but I've noticed not as clearnly as with Photoshop.

I used the same technique to build the flats after I locked the layer.

To illustrate the technique I use to make the blocks of shadows I'll use his pants as an example.

First off, I make a new layer and set it on multiply. This will be my shades layer. I use the same orange-color on all the shades for this piece to give it more unity. It also saves some time as I don't have to come up with a new and different shade color for each tone.

I blocked in all the areas I wanted shaded with the basic fold shapes using the Paintbrush.

Then I use the Eraser to adjust the jagged and messy areas as I see fit. I often jump back and forth between the two tools as I work on the shades, creating and shaping areas of darkness to a more refined look.

If you don't like the tone you picked out originally you can Lock the layer and use Ctrl+Backspace to fill in the shaded areas with a different color, until you get the effect you want. (The secondary (bottom) color on your toolbar is the one the program fills with on Ctrl+Backspace command.)

Using the same shaping technique I did the highlights of his hair, but on a layer set to Screen or Normal.

I also put the layer on 'Group with previous' (Ctrl+g) so even if I painted outside the flats color area it didn't show up. Later on I'll take grouping off and clear out the excess using the following steps:

Ctrl+click on flats layer (in layer palette), select inverse (Ctrl+Shift+i), Delete (while on the 'highlights' layer). This clears all the paint outside the flats color area.

For now, using the grouping option keeps the image looking clean without having to clean it up.