adobe photoshop - How to create an artistically posterized monotone portrait?

Can anyone please tell me what this greyscale vector style is called and how can I achieve it?

_Source

I was informed I should put my image in Photoshop and adjust the levels and run the cutout filter before live tracing in AI. I cant get this to turn out right though.

The image above is a super bad 5 minute live trace after some PS tweaking to try and show you what I mean, it makes a bunch of smaller blobs of grayscale versus bigger blobs.

How can I apply a high contrast artistic effect to a monotone image, where highlights and shadows are exaggerated, and there are few shades of grey?

Answer

I found a quickish method!

You had almost all of the workflow, and the 'cutout' part that you had, is what I was missing when trying at first.

Starting with this image, because I couldn't find the one you're using:

The longest part for me was masking out the background. You may also need to add a Black & White adjustment layer after step 2 if you're using a colour image, but want monotone. Here's the workflow I used, though there may be a few 'unnecessary' steps:

1. 
   

   Paste image into Photoshop.

   
   


2. 
   

   Right click the layer in the Layers panel and choose Duplicate Image....

   
   



3. 
   

   Go to Image → Adjustments → Posterize... and adjust the first layer to 4 levels and the second (duplicated) layer to 2 levels.

   
   

   

   
   


4. 
   

   Go to Filter → Filter Gallery... and select the Cutout filter. Set the Number of Levels to 4, the Edge Simplicity to 4, and the Edge Fidelity to 2. Use it once on each layer with the same settings.

   
   

   

   
   


5. 
   

   Set the Opacity of the second (duplicated) layer to 62%.

   
   
   


6. 
   

   Add a Brightness/Contrast... adjustment layer and put the brightness all the way up, leave the contrast at 0.

   
   


7. 
   

   Mask the background if you want to, I prefer a clean background for this effect, so that's what I did.

   
   


8. 
   

   Save for Web...

   
   



9. 
   

   Drag and drop the new file on to an artboard, or use the open function, in Illustrator.

   
   


10. 
    

    Use Image Trace / Live Trace → High Fidelity Photo.

    
    

    _{Disclaimer: I cannot speak for the results in anything below Adobe CC, but I naively assume that you should get a very similar result in Adobe CS5 & CS6.}

    
    


11. 
    

    Save and grin like Ray Charles. :)

    
    

Also tried and tested on a famous image of Steve Jobs. It required 3 layers, and different opacity levels, and I found it better to run the image through PS and up the contrast after Live Tracing, the rest of the workflow was almost identical.