Step 1
Starting off with a sketch of a younger Stephen Fry, I sketched out his prominent features such as his hair, slightly narrowed nose, dreamy eyes and chubby cheeks.
Step 2
Select the Pen Tool (P) and make sure the "paths" is chosen.
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Step 3
I dragged the Fry sketch into the the main document window and resized it before tracing the face out in a layer above it. By the way, the document size is 1100 by 1300 and this makes the document window a portrait by orientation.

Step 4
After filling the path with a #f3dec6 colour, name the the layer "face base."

Step 5
Secondly, make a pen selection for the neck. Note that I didnt select both the face and the neck at the same time in one layer. This was because, I wanted to have a clear outline of the jaw area when I start painting the face.
Step 6
Fill the selection with the same base colour as the face and name the layer "neck."

Step 7
a Soft Round brush with a #bb856d colour and in between painting, switch its opacity back and forth between 20% to 30%. Name the layer "face shade." Using the Sketch as reference, trace out the features of the face and neck as shown below. This would be called the "shade" layer.

Step 8
For another layer, "dark shade." Change the brush colour to #050404 with its opacity reduced to 10%, add more shades to the face and neck. The features here are made more pronounced. Use the Blur Tool (R) to smooth out of the paintings of all the "shades" layers too.

Step 9
Over the "dark shade" layer, create another layer and call it "highlights." Set brush colour to #fef4f0 and reduce its opacity to about 30%. Paint the around the areas of the forehead, nose, cheeks, necks and ears. The result is a splash of light over the face.We'll now go on ahead to merge the "face shade" layers down to the "face base" layer by pressing Crtl+E. Also go to Filter>Noise>Add Noise and set the Ratio to give both the merged layers a slight grainy look.

Step 10
For the eyebrows we'll go to the Brushes Palette and fade the brush with the Fade Size set at 50.

Step 11
Paint the eyebrows.

Step 12
Select the Burn Tool (O), and on the "face" layer (the previously merged layers), burn out the outlines of the face. That is, the wrinkles below the eyes, the outlines of the nose and so on. With a larger brush size, burn the ares of the cheeks, chin, jaw, neck etc. The Range of the brush must be set to Highlights and its exposure reduced to 20%.

Step 13
Now set the Burn Tool's Range to Midtones (Exposure: 25%) and proceed to burn the same areas highlighted above. With the Burn brush size reduced to 1px to 2px, work on the outlines of the face and neck as well. Now the image is given more solidity.

Step 14
In a new layer, use the Pen Tool to trace out Fry's hair.

Step 15
Fill the hair with a black colour.

Step 16
Still on the "hair" layer, select the Brush Tool (B) and set its colour to #53524f and paint strips of lines on the hair. Never mind exceeding the boundaries of the hair when painting over it.

Step 17
Now for the interesting part. Select the Smudge Tool (R) and set its Strength to 80% and smear the grey lines over the hair in the form of waves. On the edges of the hair, smudge inwards. It will take your intuition to get the desired look you prefer.

Step 18
Reduce the size of the Smudge brush to 2px and create thin strains of hair. Also select the Dodge Tool (O) with an Exposure of 30% to lighten up certain parts of the hair.

