Step-By-Step: Black and white portrait

Hello and welcome to this tutorial. It's about how I did this portrait painting of Sandra Bullock in black and white.

Software: Adobe Photoshop CS6Duration: 3-4 hours

Canvas size: A3 (3508 x 4961 pixels) divided by 2

Designing these tutorial sheets and writing this text took me quite a while (5 hours?) too. I do this in my free time and just to be helpful to anybody by sharing what I know and how I work. You can have it for free, but please consider making a donation, even if it's a small sum I'd really appreciate it.
So now, let's get started!

Step 1: A basic sketch

I start my digital drawings and paintings zoomed out. Working on 100% makes you get lost in the details easily, even before you even have a solid base to work off from. By solid I mean, getting down the overall composition (wich is pretty simple in this case) and getting the (facial) anatomy right. To me it's also important to make it look alike the person I am portraying and trying to catch their personality (or what I think their personality is) in my work. This point can be a little bit confusing in the first steps, because light and shadow do really a lot for it. Like here I don't think it looks like Sandra Bullock yet. But I had a very good reference photo from the internet. Not that big but the resolution and details were very clear and sharp. I recommend everybody – especially beginners – to grab a reference thats in a good resolution and with good lightning conditions (not one of these over lit glossy celebrity photos or blurry screenshots unless you are very good. And if you are a beginner I'd additionally recommend to have a photo with simple lights and shadows. Something like this one I was using might be a little bit tough if you are just starting out in working with dark and light values. I am starting with a quite dark grey as the background color and going lighter as I continue.

Step 2: Shadows
Many people ask about what brushes were used so I mention it just in case: Except the round and oval calligraphic brush I used a custom brush that kind of reminds of chalk. But it's really not important, especially in an early stage like this. I only used it to paint in the basic tone of the hair.

After that I used the same tone to paint some shadows in. 
Now this is a little bit important; I set the layer with the sketch on to multiply and that is how the darkest grey came in. If you do this, the multiply layer might create a black instead of a dark grey. If that happens, just lower the opacity. It's something you might call a little trick: save the lightest and the darkest color in you piece until the end. I will not use black and white until the final step and instead work within greys, so that the dark grey that you see in the image below, is my darkest tone for the longest time.  

Step 2: Lights
Now everything is pretty dark and it's starting to look like something. This means it's time to add some lights. Especially the face, wich is the focal point, has to be much lighter and needs more contrasts. For this step I added a new layer below the sketch and erased some parts of the line drawing that I thought I wouldn't need anymore. Of course you can do it all on one layer as well, if you are brave enough. Obviously I wasn't and painted the lighter grey on a separate layer. When I thought it's good, I merged them together (I don't really like working with a bunch of layers).
Also I added this bright light of whatever casts it in the background. You can ignore that for now, it's not in the face. It will be mentioned in the next sheet, but I also started to define the eyes and some hair strains.

Step 4: Even more lights
After working on the eyes and hair strains a bit, another lighter grey came in. There were some areas that had to be blended together a little bit better, too. Especially on the cheeks and nose. I carefully painted them over with a larger brush (you can see it in the right bottom corner of the sheet) until it looked satisfying. The smudge-tool seems to be fascinating and useful to many people who start digital painting. Of course also professionals use it, as far as I am informed. But I want to tell everybody to be careful with smudge, dodge and burn. They all can be very helpful and useful when you know when and how to use them to your benefits. But if you are not so sure about it, it can make your work look very unprofessional. Smudging can make everything look blurry and washy, and dodge/burn can ruin your values. You know that if you want something to be done correctly, better you do it yourself. The smudge tool is also a question of taste. There are many awesome-looking, super-clean and shiny, almost unrealistic pretty images out there, and probably the smudge tool as well as many soft brushes were in use. Well this is not what I do though. I use hard-edge and painterly brushes a lot.
Anyway, I also lit up some of the hair strains and refined them with some extra brushes.

Step 5: Finishing
When I feel it coming to an end it's time for the details. If you wanted a super clean and glossy looking result, now may be the right timing to blur and smudge and blend the hell out of the painting (but be careful around the harder edges (eyes, nose, mouth) and then add the details. 
But I'll just skip that part and go right over to the details. One last lighter skin-tone was added and I finally zoomed in to 100% to work closer on the eyes, nose and lips.
Then black and white don't have to wait any longer, they'll finally get to play their role and highlight and darkest tones. You have to be careful to use them only in a very few spots and not over-use them. If they are everywhere anyway, they are not highlights anymore, right? From my memory, where I used white was in the eyes and some "dots" on the eyelid as I saw them on my reference (glittery eyeshadow I guess), on one spot on the tip of the nose and on the lips (I bet it's lipgloss).
And that's it, call it done.